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297: Legacy by Design with Naomi Hattaway

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Advent calendars give you a little treat to tide you over until the big treats. Paper chains let you break off a piece to visualize the shortened length that remains. And who hasn’t counted down the days, crossing them off with anticipation?

Especially in the corporate context, when you know you’re leaving for a new job, that final stretch can feel like forever. But what if instead of checking out emotionally and energetically you treated that time as a chance to double down on your efforts to steady the ship for those who’ll remain?

Easier said than done, sure. But try to remember what excited you about the role when you were new. Then, invite some of those things back. And, as a bonus, by leaving well, you’ll also actively participate in shaping the narrative of what people from your professional past say about you in the future.

Continuing our Intentional Support Bean Pod, it’s my pleasure to welcome back — for a THIRD time — Naomi Hattaway. A licensed realtor with endless skills and credentials, Naomi’s passion lies in community building, diversity, and accessibility in online and physical spaces.

Naomi last joined us for episode 181: Linking Arms. In it, she and I spoke about how to build inclusive global communities that start from our kitchen tables and web out.

Today, Naomi returns to help us leave well, both personally and professionally, by showing us how to proactively design our legacy. More importantly, Naomi shares ways we can reduce the trauma on the “Stayers” – AKA the people left behind – and ensure everybody feels seen.

What You’ll Learn in this Episode:

  • The red thread of your life
  • Sewing your values into your day-to-day actions
  • When it’s unsafe to be transparent about leaving
  • Acknowledging that endings are inevitable
  • “Why do you get to leave?”

Listen to the Full Episode:

Featured on the Show:

Are you part of an organization that’s about to make an ambitious shift in 2023? Do you want to establish smoother leadership transitions to shield team members from trauma-filled exits? Let’s chat!

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Full Episode Transcript:

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Hello, it is 8:00 am in New York, 3:00 pm in Johannesburg, and 8:00 pm in Bangkok. Welcome to IN TRANSIT with Sundae Bean. I am an intercultural strategist, transformation facilitator, and solution-oriented coach, and I am on a mission to help you adapt & succeed through ANY life transition.

I’m on such a mission. I barely have my voice today and I’m still showing up to talk to our very special guest today.

I haven’t even had the interview yet and I’ve already had a paradigm shift with our guest today. Now, if you know this podcast, IN TRANSIT or if you were already a listener back, when we were Expat Happy Hour, you do know our special guest Naomi Hattaway. Let me welcome you to IN TRANSIT again for the third time.

Naomi: Thank you. I’m so I did for this conversation. It’s going to be rich.

Sundae: Well, like I said, I already had a paradigm shift I’m going to tell people about it, but let me tell them a little bit more about you before we dive in. Now, this episode has a special focus on leaving well, and specifically leadership transitions. And Naomi is perfect for this based on her personal experience and professional experience. Naomi Hattaway is passionate about community building, diversity, and accessibility in online and physical spaces. She previously served in executive leadership at Habitat for Humanity in Omaha and Front Porch Investments. She also led the COVID-19 eviction prevention and rental assistance program. So you can see the work that she does is deep into the community. And in 2020-2021, the winter plan for non-congregate shelter efforts in Omaha, Nebraska.

She’s a licensed realtor. There’s the connection to living spaces and ran for the Omaha City Council in West Omaha in 2021. She serves on the board of directors for several organizations and consults with organizations on their communication strategies as well as inclusive program design board effectiveness and housing solutions. Recently, she launched #LeavingWell consulting, I’ve even watched her leave well in a recent life transition, a practice for individuals or organizations and board of directors in periods of transition. Which provides protection for organizational assets, purposeful knowledge transfers, and stability for “The Stayers” which is often overlooked and support for those leaving.

So Naomi, thank you for joining us.

Naomi: I’m so excited. It’s always so interesting to listen to your bio being read back because it’s always like, “Oh!” And that’s part of what we’ll probably talk about today is planning ahead for the legacy that you want to leave. And so thanks for having me on.

Sundae: And the thing is, if people haven’t listened to the former podcast with Naomi, you might not know. This is something she doesn’t just teach others about, she’s lived this for her life, right? You might have listened to our episode 181: Linking Arms, where we talk about being in transition together in community. And way back in 2017 we talked about this process of living globally mobile lives, which is inherently connected to leaving well and being a good “Stayer.” So, you have this on so many levels. Just deeply embedded in yourself. I know that.

All right, Naomi. So one of the things I wanted to tell the audience today is I’ve already had a paradigm shift and we haven’t even talked about it. Naomi and I were together speaking just over WhatsApp quickly about this episode and what we could talk about. And Naomi, you talked about this idea of legacy and leadership. And, for me, maybe I’m naive, but I always thought about legacy, like what you leave behind after you serve, and if you’ve done In a good job, you leave a wonderful legacy, right? And what you’re telling me is that a legacy is actually, you have an opportunity to think of it as a path you set forth in advance and with intention. So can you say more about that?

Naomi: Yeah. And I first need to give some deference and some props to our mutual friend Jerry Jones, who wrote about the concept of leaving well and kind of brought it to the forefront in terms of expat life, in terms of the moving and the leaving well. I had a lovely chat with Jerry and said, “Do you mind if I kind of take that and put it into this leadership space?” So I just wanted to give a shout out to Jerry.

Going to the concept of that legacy my husband and I when we moved to New Delhi, India, he kept saying to me, “It’s like you’re on this 100 year plan.” And I’m like, “What are you talking about?” And he said, “I go,” in his work, “from the airport to work, to the office to home, back to the office, to the airport.” He travels a lot and he said, and that legacy that, what I’m leaving behind is a shorter runway. So he’s in private aviation world, serving things very aviation based, but he said, “My runway is shorter on the legacy that I’m leaving.” He said, “Your work is creating legacy 100 years deep into the future.”

And we’ve been riffing on that a little bit as a family and I’ve been thinking about it in my life, if we flip the switch and toggle forward-thinking instead of only in the back, that lets us lay out this beautiful runway of, “What do you want your legacy to be? How do you want it to align to your values?” And then you can pull in whatever you’re working on. A project. A team you’re working with. Whether it’s an individual journey. Whether it’s even as simple as preparing for your own death, which is something we all have to face. You can then lean into your values and lean into a way that really does create that legacy.

So a lot of times we also think about the red thread of our life and looking back, what are the things that that that stay true as we navigate different things and navigate different projects and experiences. And we always look back and say, “Well, that’s the red thread.” My personal red thread is around housing stability and community. Well, if I instead flip that to the future, how does everything else that I do in my life, how can that contribute to my legacy? And I think it comes back to Sundae, it may feel morbid for people who haven’t thought about it but if we are all going to die one day, what if we instead looked at our remaining time on this earth as intentional and purposeful? So that you could almost, and this is where it sounds a little morbid, if you think about what you want people to say about you at your funeral or at your celebration of life, we can design that today. We could design what people will say about us in our future, today.

And so I think there’s some, there’s some real meaningful opportunities there to have the legacy before. We’re thinking, instead of just the reverse.

Sundae: Well, I think it ties into my idea about how I want to live abroad without regrets. I’m gonna live without regrets and not that we don’t make mistakes and wish we had been more savvy, it doesn’t mean that. It means, how do we live intentionally? And there’s this word, this word legacy, I find, I’ve also heard another context and people feel shy to even think about the word legacy because it’s like legacy is only deserving to the famous, only deserving to the super successful. And when I hear you talk about legacy, I’m actually hearing it in a lens of, let’s just be really intentional about living our values and the impact we want to make.

Naomi: Well and how do you want to be known? I think that at our core we all crave a place where we can belong and we all crave to be known for who we are. Well, if we actually get to design a little bit of that, how much more power does that give us? And it can be, it can be kind of in a small little box. It can be that I want my legacy to be that I was kind. And how much pressure does that take off? Just to take kindness into everything that you do in the future? Or it can be big things. It could be, it could have numbers and metrics attached to it. It could be that it could be something huge. Like in my legacy, I want it to be that I impacted homelessness and the prevention of that. So I think you can play around with it a little bit, right?

I think the other beauty of creating a legacy intentionally and thoughtfully is that you can bring your loved ones into the mix and ask them, “Am I living into this? Will you help hold me accountable and check me when you notice that I’m strained from what I want my legacy to be?” So, yeah, I think that’s powerful and I think then the other thing too, is we all need to take this into account, even if you don’t think that you’re in a space that you hold a lot of decision-making power or a lot of control over your destiny. And I kind of air quote that because we all do have that control. We need to be thinking about it actively and regularly because we can’t think about it when the time comes, we have to be thinking about it proactively.

Sundae: So, tell me more about how you came to focus on this. I mean what was it that led you to this clarity?

Naomi: So you know, it’s interesting. I have been in the last three to four years, I’ve been diving and dipping in and out of other people’s systems. So I’ve been a project manager that has come in to help accomplish something. I’ve been asked to come in and help fix or come in and help steady. And I’ve just been realizing that I think that part of the problem is that we are churning out leadership folks that don’t prep for their own legacy. And so then we’re all just kind of flailing in the wind. And then not only that. But we have kind of this broken system where people leave a project or a thing or a role or an organization and they haven’t prepped to leave. And so then they can’t also work on staying well the next place. And then the other piece that’s really tragic is that we don’t help ready or steady the ship for the people that are staying, whenever that transition happens.

So I think it happened, Sundae, because I was privy to but not emotionally connected to all of the trauma that’s happening as people leave projects, or as people try so hard to valiantly show up every day for their work. But there’s no purpose, there’s no riverbanks, there’s no like guideposts. And that’s kind of where it was like, “Oh, well, we’re forgetting our values. We’re forgetting why we said ‘yes’ to this project or the job in the first place.” And then when we don’t remember why we said, “Yes.” And we also don’t have riverbanks that guide our work. It just kind of it makes it messy. Give you an example.

Someone called me recently and said, “I think that I’m going to be leaving in the next six to nine months. I’m just tired. I think I’ve done my job and I’d want to know what you would suggest for me.” And I said, “Well, the first thing you need to do is get a big sticky paper and write out all of the things that you wanted to do when you first started this job. Start identifying the things that you’ve accomplished. And then what’s left? What are the things that you wish you wanted? That you really want to do.” And in that way, her next six to nine months can be so laser focused on two or three of those things so that when she leaves, she knows that she has done what she meant to do. And then it also sets up again, how does she want to be known as she leaves this, this next role?

Sundae: Yes, it’s such a different energy than, like, waiting it out. You know, if we take it from a globally mobile space, right? When you’re like, “Oh we have the next assignment, we’re leaving in 6 months,” you almost like check out energetically and emotionally. And you’re just like, you’re gone, you’re gone, you disconnect. And what you’re saying is, “No, that’s when you dig deep.”

Naomi: I think you can do both. I think you can dig deep. So to use the example of being a globally mobile person who has the next assignment coming, we do check out. And you start, you get your timeline that you use the last move and you start checking the boxes of what you need to do for the next role for the next location. But I think we are so resilient as humans. We can also dig deep in the place that we are currently. Going back to Jerry’s leaving well concept, there’s all of these like real time solutions that you can implement.

For us, when we’ve moved locations, we make sure that we go back to the favorite places. We make sure that we go back to say goodbye to our favorite wait staff. We make sure that we take photographs of the things that really matter to us. And so those things can also be applied to the leaving well concept in our careers, our professional lives.

I think also you know when you think about leaving a place, most often you have a relationship with the people that you work with or even a relationship to the outcomes that you were tasked with. And if you don’t say goodbye to those things and I think that sounds a little like, whoo. But if you don’t intentionally say, “Thank you.” Thanks for what you brought to me. Thank you for the opportunity to have this moment. This outcome, this work.” I think that it also doesn’t set us up for success in the thing. So, there’s a lot of reasons to leave well and make it a practice.

Sundae: Yeah. And I think it would absolutely change the quality of your weeks, right? Instead of being bogged down by like the operational demands, it adds another layer. And what I’m hearing is when you’re living in alignment with your values and you have personal purpose and meaning in what you’re doing, it changes how you engage in your operational day-to-day.

Naomi: Well and think about too, the difference between if you imagine a typical office setting. I know folks are doing remote and people are doing virtual work now. But if you think of a typical office setting where traditionally people are sharing the same space, think of the outright difference between someone who has checked out and has another 30 or 60 days, versus someone who’s coming in and saying, “I have this much time left. What can we do today? How can I help you today? To make sure that you have what you need.” It just shifts everything. And not only that but it becomes this really beautiful opportunity for modeling behavior and then the ripple effect of leaving well with the folks that stay, whether they know it or not they’ll pick up on that same energy. It also helps them welcome the next person in a much different way than if there hadn’t been intention. So it just becomes this really holistic and beautiful opportunity.

Sundae: Exactly. So what if you already have a leadership position and you haven’t thought forward. You’re like actually it’s a great idea, but where do I start?

Naomi: So I think it goes back to the values. I think there’s all sorts of places that you can get a list of common values. So I would encourage everyone to Google, list of values. It’ll pop up and you can spend some time circling the things that pop out to you in our really immediate values that you identify with and then pull the top three to four of them. And then that into a document, make it a living document. A Google doc or whatever you can use that, maybe it’s handwritten. But start to identify how those overlap and how you already see those in your day-to-day life.

So for me, one of mine is kindness. So if kindness is a value for me, am I bringing that to work every day? Am I bringing it to the way that I schedule a meeting? So for me, this sounds very, very rudimentary, but a kindness value for me lives out when I schedule a meeting, I make sure that I have a pre-read. So if you don’t already know about my organization, here’s a link in the calendar invite, and here’s the agenda that we’re going to talk about. And by the way, I only schedule for 45 minutes so that you have time for a bio break for your next.

So that seems like it’s like, “Oh, that would be lovely.” But it goes back to very intentionally. I’ve done it because of the kindness value is something that I want to live into. So what happens then is when I leave a project, if people say, “What would you say about Naomi?” “Oh she was kind, she only ever scheduled 45 minutes.” And I always remember that. So I think you can just take it bit by bit. Find those values that you identify with for your life and then start to see how you can attach them to your work.

The other thing I think I would say for someone who’s currently in a role and thinks, oh maybe there’s no time or it feels too hard of a slog. If you think about the things that you were excited about when he first took the role or when you first were asked to apply for the job. What were the things that were so exciting? Oftentimes, we lose those and they fall to the bottom of the pile because the day-to-day operations take over. So remembering those things and seeing, can you invite those things back? Can you invite the excitement back? What are the things that felt too big that someone told you you couldn’t accomplish and so you set those to the side? Revisit those, because those things can also be legacy.

One other thing I’ll say Sundae and this is a very practical set of advice. But the most beautiful way you can leave well is to set up a structure or framework so that those that come behind you don’t have to do so much work to keep it going. So, that’s another really practical thing you can do is start to lay out a framework of, where does someone find the things that I’ve put together? Where does someone find the frameworks that I’ve laid, so that that can be left behind as well?

Sundae: Mmm, so good and I wanted to just mention here, we’ve talked about an office, right, but there’s so many other ways that we lead whether its corporate context or in the community organization, a religious or spiritual community, that I think these ideas definitely apply beyond let’s say a corporate context, right?

Naomi: Yeah.

Sundae: I just think how much power this has to create more meaning in your everyday life, right?

Naomi: Well, and if you think about too, so you mentioned community organizing and that’s a really good example. Often times something will happen in our world or in our private spaces, or in our small communities, where we have a reaction to something. And I won’t name examples because they could, depending on your audience, people will have different reactions. But think of a thing that makes you react. You know, like, “Oh my gosh, we cannot have this in our community. I am going to go fight the good fight.” I can guarantee you that for everything that you have that visceral reaction to, someone has already been working on it. You’re not the first. And so the problem though is that the people that have been working on it before you maybe didn’t leave artifacts? Maybe they didn’t think the trail that you can go pick up on. And so, that’s another really beautiful way that we can step into and embody leadership in this leaving well, is that if you’re working on something, leave something behind. Leave the little breadcrumbs, leave an artifact of some sort that people can then pick up the mantle and then carry forward.

So I think that goes back to kind of that framework and the structure. Scaffolding almost if you will. And then this is leadership by preparation. I think comes into play when we think about our end-of-life planning and how well we can leave a legacy that way.

Sundae: My whole body just like shuts down when you start talking about that because I’m like, “Not going to happen.” Like I know I just completely go into like denial.

Naomi: I know. I know. And you know what I think. I think that for all of us as humans we have The most ability, we have the highest ability to attach when something’s happened to us. And so I did not fully understand how important this was until I was asked to manage my uncle’s estate. And it was like, “oh if only he had done…If only he had thought forward about his legacy.” Because part of his legacy could have been, “I’ve organized it for you all so that you are not having to scramble and argue and grieve.”

So that all you have to do as part of my legacy is grieve and remember. Shutting down is the natural reaction and itching into it just a little bit more to say, “Okay. It’s going to happen. What’s the small thing I can do to help protect that legacy?”

Sundae: I’m actually going to put a link to a podcast episode I did with an expert on estate planning to help keep this conversation going and to keep myself accountable. Because it is. It’s an act of love to prepare for your loved one’s. To take that he’s away. I’ve also been privy to what happens when you are responsible for the estate. And it’s like a second job for six months, right? So you work full-time during the day and then you go home at night and you do that for six months and that’s heavy, it’s heavy.

Naomi: It is heavy. And not only that, it goes back to that what are we asking others to do because we didn’t plan for our legacy? So it’s in the job space, it’s in our personal spaces, and it’s in that end-of-life space. So if I have not prepared for my kind of life, I’m asking my family to bear the brunt of that when all they should be doing is grieving and celebrating. In a professional space, if I haven’t prepared for my legacy, I’m asking others to pick up the slack for my absence, and their own jobs and prepare for the new person coming in. So there’s a way that we can bring in caretaking for each other, community care, and protecting our legacy and preparing for it.

Sundae: It makes me want to ask something kind of pragmatic. When someone’s going to leave an organization is actually nobody’s business until you make that decision, right? But once you do, and it’s officially communicated, a lot of people are implicated. What do you think about people being transparent about thinking about leaving before they’ve actually made that decision?

Naomi: So I’m glad you brought that up. So every time that I have managed a team, whether I’m the official manager, or I’m project managing I say right off of the bat endings are inevitable. So we are all going to leave. None of us, literally, none of us still have our first job. If that’s true and then we can say, “Well endings are inevitable, how can we plan now? So people get a little bit weirded out about this. But when I first come into a project team management situation, I say, “Let’s all get our resumes out. Have you updated it? Is your current work that you’re doing on your resume?” And they’re like, “Why would it be on my… I don’t have plans to leave.” But it’s in that very practical like, “Well, then let’s all stop and do that together. Let’s come back to the next meeting and make sure that we’ve updated our resumes.

And that’s just kind of lets everyone breathe a little bit easier. Like, “Oh, let’s all just get prepared together,” so it’s not this one sneaky suspicion that someone might be leaving. The other thing that I think is a really practical way to do it is to just talk about, in the US we call them SOPs, Standard Operating Procedures. A simple check of, what are the two top things that we should get on paper right now in case something happens to one of us? I think we can talk about it in that way too. It doesn’t have to be a transparency that I am planning on leaving. It can just be, we should protect the organization by making sure that if and when one of us leaves, we’ve got some things in place.

Having said that though, I do value for folks who can, I think there’s a lot of folks who are in working situations where they’re not safe to be transparent about their leaving. But there’s a way that you can word everything to say, like even just too say like, “Gosh, we’re all gonna end up leaving someday. So what is it that we could do today to best protect the organization.” And that doesn’t bring up any red flags, I don’t think, my to protect the organization. Of course, everyone would want to.

The other thing that I think that is really, really helpful is for managing leaders. So people who have people under their care to ask, “What is it about your job that you want to lean into more? What is it about your role that you’re not having growth opportunities?” And that can also start that conversation about what might be next. And I learned this when I was doing volunteering, I would raise my hand for everything, and not until I realized that if I sat on my hand, it gave someone else an opportunity. And so I think we could shift our thought process there. As well being in a position, we can outlive our positions and so someone may be else should come in, which makes it a little bit more natural to talk about leaving. Not a negative.

Sundae: Absolutely. I remember one of my leaders that I had years ago on my first day, he was like, “So for you to really make a contribution, I’d expect you to stay for two or three years.” It was just really liberating to hear, to have that conversation about expectations and open the door of, “You will probably move on one day,” right? And I appreciate that. I’ve had two people who have said that like, “For this to be worth it for us and for you, let’s try to commit to this timeframe.” And I think that’s nice.

Naomi: From a human resources, people perspective, it costs an organization so much money to have to fill a position. And so if there’s a little bit more transparency on the front end of like, “Let’s talk through.”

We’ve talked a lot about the leaders. Do you mind if we shift our attention a bit to the “Stayers?” So what do we need to know?

Naomi: Well, I think that there’s a feeling of abandonment and feeling of, I think it’s very easy for “Stayers” to feel it it’s personal. I think even if we look at it from a globally mobile perspective of changing postal codes and zip codes the “Stayers” often feel like they’ve been left behind. And so, I think that there’s really beautiful ways in a corporate or in a professional work setting to just acknowledge that that is true and it is normal to feel abandonment. I think there’s also a lot of times feelings come up of jealousy, and being kind of at a covetous space of like, “Why do they get to leave? And why am I stuck? Or why do I have to stay?”

So I think for “Stayers” I think the one thing that I would suggest is if those feelings especially of jealousy come up, what is it that’s keeping you from exploring? What might be next and what is it that’s keeping you from wanting to also protect and create your own legacy? Don’t make it a victim mentality. You can honor the feelings but then move right into doing the exact same thing. Identify your values. Do your value still align with your project or your role or your company that you’re with?

The other thing I would suggest and this is going to feel maybe not so great or effusive. But offer to the person who’s leaving, ask them what they need in order to help them leave well. Oftentimes it would be something like, “Can you help me build this framework? Can you help me capture and document the artifact?” And that also then becomes resume builder. If you’re the person that helped provide that structure, if you’re the person that helped bridge that transition that also helps if you want to stay in the future of your organization. If you’re the one that helped create stability, make sure that that’s known. Step into that space.

The other thing, I think that’s really important for “Stayers” is to just be present, notice, and listen. There’s a lot of trauma that comes with transition even when it’s done well. And I think for folks that stay behind, listen for the opportunities where you can provide support to each other, be present about how you’re feeling, and how you’re showing up. And then I guess I would just say again, it’s an opportunity to check in with your values and make sure that they’re still aligned.

Sundae: Right? Exactly, that’s great. And honestly, it’s so obvious when I hear it now, but I don’t know if people are using that same transition lens.

Naomi. I don’t think so. No, I don’t think so. But it comes back to your question like, where did that come from that we assume that loyalty is the kingpin of what we are signing up for when we take a job or a role or a project? I think about there’s another example I can give, I was volunteering for a women’s circle is the easiest way to explain it. I was in a president role and you serve for two years. Well, I knew a year ago that I needed to be done. And so I could have either stuck it out, slogged for it, counting down the days. Almost like, remember making paper chains–

Sundae: Yes for Christmas.

Naomi: Yes could have had like a chain probably of like, “One more day done. Thank goodness.” Or I could make the paper chain and on each one of them have something that I wanted to intentionally do that day. So I did that and I laid out the year and I dug in really, really deeply on:

  • How did I want the remaining leadership team to feel when I left?
  • How did I want them to feel on my last meeting?

Then I backed that out. So if the outcome was this:

  • How do I want to feel?
  • How do I want them to feel?

Then I backed it out over the course of time that I had and then it became really, really practical small little things every day that led up to and connected to a really good leaving well.

Sundae: I mean these are all very familiar coaching practices of like creating the visualization of it and then working back and checking in, the accountability and it actually doesn’t take that much time.

Naomi: It doesn’t take that much time. And I think one thing that might be helpful for anyone listening is the common response I get is, “But my boss would never go for this.” Or, ”It’s going to feel weird if I suggest this.” You just have to do it anyway. So I think what I would suggest, any time you have a concept that you can name, it makes other people curious or it lets people kind of embrace it. So it literally physically say, “I would like to try practicing leaving well. And what that means for me is…” and then you fill in the blank. I guarantee you that there’s going to be some interest and some intrigue, and some curiosity. At the very minimum, they’ll be like, “Okay, cool, whatever.” They’ll be like, “Sure, you do what you need to do.” And then just naming things signaling that out lets people start to adopt it and before you know it, they’ll also start to be intrigued by it. And they’ll be ready to kind of come alongside you, link arms with you, and the leaving well process.

I left a job a couple of years ago and I said, every time, “As I leave, I want to make sure I leave well. As I leave, I want to make sure I leave well. As I exit, I want to make sure that you felt that I’ve left well.” And just you know, the boss who is still there calls me on a regular basis and says, “You know someone else just left and they left well.” So we remember, right? And so if you just name it and speak it, it’ll be a lot easier for other people to come along.

There’s also some books and some recommendations of ways that you can kind of inject it, Necessary Endings by Dr. Henry Cloud is a fabulous book. The First 90 Days. The button up summary is when you’re intentional about how you leave you are setting yourself up to not only enter the next thing well, but you’re also creating a ripple effect for those that stay behind.

Sundae: Well, and there’s a couple of the things I keep going back to purpose and meaning, it just seems so much more meaningful and that is rewarding for everybody. The other thing is, it doesn’t take very much time. It’s literally just this intention 20 minutes here, half an hour there to get clear.

Naomi: And I think about from a hiring organization’s perspective as well, they want good apples, if you think of the bad apples ruin the whole entire barrel concept, they want good apples to leave because that reflects back on their organization. So, if I’ve left well and if my organization as allowed me to leave well, I will likely talk about that organization in much higher terms and in much more glowing ways than if I hadn’t left well. And so, it’s really in everyone’s best interest to practice, and it’s a practice. It has to be formed.

And the other thing too is there’s no one way to do it. It’s going to look different for everyone but I think you hit the nail on the head when you said it doesn’t take that much time.

Sundae: I just why aren’t we doing the things that will make such an impact that are so light. And it’s also not expensive, you can do some of these reflections on your own. Yes, you can work with a coach, but it’s about intentionality.

Naomi: Maybe it’s a list of passwords, maybe it’s a list of the things that I didn’t get done yet. But here’s the framework that I started. So there’s all sorts of ways that you can set yourself up to with having a list to reflect on that also doesn’t cost much money.

Sundae: I just think about often when we come into a new position, we’re very focused on understanding the organization delivering. And we don’t go on the mental level. So, I think it’s wonderful. This conversation, I’m just thinking about intentionality, I’m thinking about values. How can we talk about knowing– How do I know when it’s time to go?

Naomi: Yeah, so it’s going to be uniquely personal for everybody, but if we lean into our intuition in our gut, we all know. We all know when there’s something that doesn’t quite align anymore, and I will be really intentional in saying, non-alignment isn’t always icky. It’s not always something that feels terrible or is negative or feels tiresome. Sometimes a non-alignment is either a calling to something else. I wouldn’t say a higher thing, but It’s a calling to something else or just a natural shift in organization as it has different leadership in place. Or as it has a null say leadership by title or as their mission shifts. It might just be that you start pulling away.

So I think that often we assume that a no longer fit is bad. No longer fit can also be really, really empowering and really beautiful. If we are so aligned with what our values are, we will know. And when you know, I think that’s an opportunity to go back to whatever your self-care or whatever your personal wellbeing things are. Whether it’s journaling, time with friends, time outside. Ratchet that up a notch. If you have that feeling of knowing that it’s time, spend some self-awareness time to check in.

The other thing that I think is not often talked about is sometimes it’s time to go and we know because someone else is a better fit. If you have someone that reports to you or that works with you, that you see might be a better fit for what you’re working on. That’s also a really, really incredible leadership opportunity to say, “Maybe it’s this person.” And that’s an opportunity to have really, really beautiful leaving well conversations inside of your organization or project. To say, “I want to maybe flag that this person would be great for this role.” That’s a powerful leaving well opportunity, if you know.

Sundae: Yeah, absolutely. And I also just want to use this opportunity to also say thank you to you when I was in a transition with my community, right? With my podcast. I wasn’t leaving anybody. But I was leaving one sort of scope and moving into the other and that’s what you and I talked about during that time is processing, like, how do I feel about that? It wasn’t a misalignment, it was just a shift, a shift. And then, how do I do that? And how do I do that intentionally and with care? And so, that I’ve had your support on that process and I know how much that helped with that transition.

So we’ve talked about it from like it organizational perspective. And I would even say that’s valuable within your own business, right? If you’re shifting even your niche or who you work with those same principles also apply.

Sundae: Do you mind if we turn the attention to you a little bit, you’ve given us so much on these concepts of leaving well and being good “Stayers.” Also, how an organization can really nurture that process. But I want to know a little bit about your own process right now. Now that I have Ambitious Transformation in Transition, do you mind telling us a little bit about what is in transition for you right now? What? Which ones are you feeling? Yeah, so say more.

Naomi: So transformation that I’m currently experiencing. So in my personal life, we have just moved, we moved from a two household situation, and combined our households back into one location. So that’s been an interesting transition. I’m also In the process of leaving employment to go to a contract position. So I’m changing the legal status of how I interact with my work and it’s interesting because that felt like not a big deal. It’s just a legal status, I’m no longer an employee, I’ll be a contractor but it has caused or has given me an opportunity to really lean into practicing leaving well, because I’m leaving a team behind. They feel that they’re being left behind in a certain way. And so, It’s been a beautiful way to practice that transition.

I’m also working towards a transition of just literally how I live my life. You brought up the concept of ease before and ease is something that I am chasing so so valiantly. I want my mornings to be full of ease. I want my decisions to be more at ease. And it goes back to the values and riverbanks. If I know that this is what I stand for or this is the work that I want to do, it makes the “nos” so much easier, and there’s so many other people out there who can do the work that I say no to. So, that’s a transition for me. When I reflect back, I’ve lived a lot of my life in chaos and franticness and fast-paced. Need to do it all need to have it all and I’m really pushing all of that to the side. So that’s been a transition that will be ongoing. I know it will be a journey but I’m inviting welcoming and chasing ease.

Sundae: I’ve watched you live that. I’ve watched, you have all of the things. All of the good things but then make choices make tough choices to get to where you’re at right now. So what is ambitious for you right now? As you know, I define ambitious as has to be outside of scope or scale of any sort of definition. It has to come from you. So what is ambitious for you?

Naomi: So what’s the first thing I thought of when you said that about what’s ambitious, I’m writing a book, and while that might not seem super ambitious.

Sundae: Are you kidding me?

Naomi: I mean, I write. And so like you know, if anyone who’s a blog writer or constantly is in writing spaces to write a book, it seemed initially to me like, “Oh, I yeah, I’ll do that.” But what I’m finding is that because it is part memoir, there’s a lot of healing that is going to take place that I wasn’t prepared for. I’m also going to combine the tarot, the major arcana with this book. And so there’s a lot of research that I’m not accustomed to. I’ve always written kind of from the heart and from the hip.

And so the ambitious piece is coming in needing to really plug into doing right by this book. And I think that feels ambitious to me to lean into the hard and lean into what doesn’t come naturally. So that I can put out this thing and do right by it.

Sundae: That’s so exciting. I can’t wait to hear more.

Naomi: So well I printed I printed the manuscript someone said, “Do not let it just live digitally. You need to print the manuscript and hold it.” And oh my goodness. That was a huge shift.

Sundae: Oh, I bet that felt amazing too.

Naomi: It felt amazing and terrifying too.

Sundae: Well, you have to keep us posted on that. And we will put links to all of your spaces and places, and please come back to us when the book is live so that we can also include that their. You have so much to offer Naomi. And I get all teary when I talk about it now. But you know, I met You in 2018 and in person, although I knew of you before. And you have always, of course, you’re talking about leadership, you came talking about community before. You’ve just lived all of these principles so fully and so future-oriented, that’s something I’ve always respected about you. And you do the right things, even though they’re the hard things. And that’s something I really appreciate. And it’s so interesting that you bring in ease in the heart, if that makes sense. Like you do already bring in ease, at least four others. That’s something you see you do all the time. So you being a role model for this, you living that also sets a path for other people and you’ve been laying that path for me and many moments of my own life and I just wanted to say thank you. Because I don’t know if you realize how much of an impact that’s made.

Naomi: Thank you.


Sundae: So thank you. I did that without getting to teary. All right, so I think it’s about time, we have to close up here. I think we need to talk about this more. I think we can look at where we’re leaders in our life and apply that immediately. I think as “Stayers” we also have agency. Even if the leader doesn’t want to leave well, we can also do that. And I am just so grateful. So thank you everyone for listening to IN TRANSIT with Sundae Bean. Always a pleasure to have you here with me. I’ll leave you with the words of Tim McGraw: “We all take different paths in life, but no matter where we go, we take a little of each other everywhere.”

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Advent calendars give you a little treat to tide you over until the big treats. Paper chains let you break off a piece to visualize the shortened length that remains. And who hasn’t counted down the days, crossing them off with anticipation?

Especially in the corporate context, when you know you’re leaving for a new job, that final stretch can feel like forever. But what if instead of checking out emotionally and energetically you treated that time as a chance to double down on your efforts to steady the ship for those who’ll remain?

Easier said than done, sure. But try to remember what excited you about the role when you were new. Then, invite some of those things back. And, as a bonus, by leaving well, you’ll also actively participate in shaping the narrative of what people from your professional past say about you in the future.

Continuing our Intentional Support Bean Pod, it’s my pleasure to welcome back — for a THIRD time — Naomi Hattaway. A licensed realtor with endless skills and credentials, Naomi’s passion lies in community building, diversity, and accessibility in online and physical spaces.

Naomi last joined us for episode 181: Linking Arms. In it, she and I spoke about how to build inclusive global communities that start from our kitchen tables and web out.

Today, Naomi returns to help us leave well, both personally and professionally, by showing us how to proactively design our legacy. More importantly, Naomi shares ways we can reduce the trauma on the “Stayers” – AKA the people left behind – and ensure everybody feels seen.

What You’ll Learn in this Episode:

  • The red thread of your life
  • Sewing your values into your day-to-day actions
  • When it’s unsafe to be transparent about leaving
  • Acknowledging that endings are inevitable
  • “Why do you get to leave?”

Listen to the Full Episode:

Featured on the Show:

Are you part of an organization that’s about to make an ambitious shift in 2023? Do you want to establish smoother leadership transitions to shield team members from trauma-filled exits? Let’s chat!

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Full Episode Transcript:

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Hello, it is 8:00 am in New York, 3:00 pm in Johannesburg, and 8:00 pm in Bangkok. Welcome to IN TRANSIT with Sundae Bean. I am an intercultural strategist, transformation facilitator, and solution-oriented coach, and I am on a mission to help you adapt & succeed through ANY life transition.

I’m on such a mission. I barely have my voice today and I’m still showing up to talk to our very special guest today.

I haven’t even had the interview yet and I’ve already had a paradigm shift with our guest today. Now, if you know this podcast, IN TRANSIT or if you were already a listener back, when we were Expat Happy Hour, you do know our special guest Naomi Hattaway. Let me welcome you to IN TRANSIT again for the third time.

Naomi: Thank you. I’m so I did for this conversation. It’s going to be rich.

Sundae: Well, like I said, I already had a paradigm shift I’m going to tell people about it, but let me tell them a little bit more about you before we dive in. Now, this episode has a special focus on leaving well, and specifically leadership transitions. And Naomi is perfect for this based on her personal experience and professional experience. Naomi Hattaway is passionate about community building, diversity, and accessibility in online and physical spaces. She previously served in executive leadership at Habitat for Humanity in Omaha and Front Porch Investments. She also led the COVID-19 eviction prevention and rental assistance program. So you can see the work that she does is deep into the community. And in 2020-2021, the winter plan for non-congregate shelter efforts in Omaha, Nebraska.

She’s a licensed realtor. There’s the connection to living spaces and ran for the Omaha City Council in West Omaha in 2021. She serves on the board of directors for several organizations and consults with organizations on their communication strategies as well as inclusive program design board effectiveness and housing solutions. Recently, she launched #LeavingWell consulting, I’ve even watched her leave well in a recent life transition, a practice for individuals or organizations and board of directors in periods of transition. Which provides protection for organizational assets, purposeful knowledge transfers, and stability for “The Stayers” which is often overlooked and support for those leaving.

So Naomi, thank you for joining us.

Naomi: I’m so excited. It’s always so interesting to listen to your bio being read back because it’s always like, “Oh!” And that’s part of what we’ll probably talk about today is planning ahead for the legacy that you want to leave. And so thanks for having me on.

Sundae: And the thing is, if people haven’t listened to the former podcast with Naomi, you might not know. This is something she doesn’t just teach others about, she’s lived this for her life, right? You might have listened to our episode 181: Linking Arms, where we talk about being in transition together in community. And way back in 2017 we talked about this process of living globally mobile lives, which is inherently connected to leaving well and being a good “Stayer.” So, you have this on so many levels. Just deeply embedded in yourself. I know that.

All right, Naomi. So one of the things I wanted to tell the audience today is I’ve already had a paradigm shift and we haven’t even talked about it. Naomi and I were together speaking just over WhatsApp quickly about this episode and what we could talk about. And Naomi, you talked about this idea of legacy and leadership. And, for me, maybe I’m naive, but I always thought about legacy, like what you leave behind after you serve, and if you’ve done In a good job, you leave a wonderful legacy, right? And what you’re telling me is that a legacy is actually, you have an opportunity to think of it as a path you set forth in advance and with intention. So can you say more about that?

Naomi: Yeah. And I first need to give some deference and some props to our mutual friend Jerry Jones, who wrote about the concept of leaving well and kind of brought it to the forefront in terms of expat life, in terms of the moving and the leaving well. I had a lovely chat with Jerry and said, “Do you mind if I kind of take that and put it into this leadership space?” So I just wanted to give a shout out to Jerry.

Going to the concept of that legacy my husband and I when we moved to New Delhi, India, he kept saying to me, “It’s like you’re on this 100 year plan.” And I’m like, “What are you talking about?” And he said, “I go,” in his work, “from the airport to work, to the office to home, back to the office, to the airport.” He travels a lot and he said, and that legacy that, what I’m leaving behind is a shorter runway. So he’s in private aviation world, serving things very aviation based, but he said, “My runway is shorter on the legacy that I’m leaving.” He said, “Your work is creating legacy 100 years deep into the future.”

And we’ve been riffing on that a little bit as a family and I’ve been thinking about it in my life, if we flip the switch and toggle forward-thinking instead of only in the back, that lets us lay out this beautiful runway of, “What do you want your legacy to be? How do you want it to align to your values?” And then you can pull in whatever you’re working on. A project. A team you’re working with. Whether it’s an individual journey. Whether it’s even as simple as preparing for your own death, which is something we all have to face. You can then lean into your values and lean into a way that really does create that legacy.

So a lot of times we also think about the red thread of our life and looking back, what are the things that that that stay true as we navigate different things and navigate different projects and experiences. And we always look back and say, “Well, that’s the red thread.” My personal red thread is around housing stability and community. Well, if I instead flip that to the future, how does everything else that I do in my life, how can that contribute to my legacy? And I think it comes back to Sundae, it may feel morbid for people who haven’t thought about it but if we are all going to die one day, what if we instead looked at our remaining time on this earth as intentional and purposeful? So that you could almost, and this is where it sounds a little morbid, if you think about what you want people to say about you at your funeral or at your celebration of life, we can design that today. We could design what people will say about us in our future, today.

And so I think there’s some, there’s some real meaningful opportunities there to have the legacy before. We’re thinking, instead of just the reverse.

Sundae: Well, I think it ties into my idea about how I want to live abroad without regrets. I’m gonna live without regrets and not that we don’t make mistakes and wish we had been more savvy, it doesn’t mean that. It means, how do we live intentionally? And there’s this word, this word legacy, I find, I’ve also heard another context and people feel shy to even think about the word legacy because it’s like legacy is only deserving to the famous, only deserving to the super successful. And when I hear you talk about legacy, I’m actually hearing it in a lens of, let’s just be really intentional about living our values and the impact we want to make.

Naomi: Well and how do you want to be known? I think that at our core we all crave a place where we can belong and we all crave to be known for who we are. Well, if we actually get to design a little bit of that, how much more power does that give us? And it can be, it can be kind of in a small little box. It can be that I want my legacy to be that I was kind. And how much pressure does that take off? Just to take kindness into everything that you do in the future? Or it can be big things. It could be, it could have numbers and metrics attached to it. It could be that it could be something huge. Like in my legacy, I want it to be that I impacted homelessness and the prevention of that. So I think you can play around with it a little bit, right?

I think the other beauty of creating a legacy intentionally and thoughtfully is that you can bring your loved ones into the mix and ask them, “Am I living into this? Will you help hold me accountable and check me when you notice that I’m strained from what I want my legacy to be?” So, yeah, I think that’s powerful and I think then the other thing too, is we all need to take this into account, even if you don’t think that you’re in a space that you hold a lot of decision-making power or a lot of control over your destiny. And I kind of air quote that because we all do have that control. We need to be thinking about it actively and regularly because we can’t think about it when the time comes, we have to be thinking about it proactively.

Sundae: So, tell me more about how you came to focus on this. I mean what was it that led you to this clarity?

Naomi: So you know, it’s interesting. I have been in the last three to four years, I’ve been diving and dipping in and out of other people’s systems. So I’ve been a project manager that has come in to help accomplish something. I’ve been asked to come in and help fix or come in and help steady. And I’ve just been realizing that I think that part of the problem is that we are churning out leadership folks that don’t prep for their own legacy. And so then we’re all just kind of flailing in the wind. And then not only that. But we have kind of this broken system where people leave a project or a thing or a role or an organization and they haven’t prepped to leave. And so then they can’t also work on staying well the next place. And then the other piece that’s really tragic is that we don’t help ready or steady the ship for the people that are staying, whenever that transition happens.

So I think it happened, Sundae, because I was privy to but not emotionally connected to all of the trauma that’s happening as people leave projects, or as people try so hard to valiantly show up every day for their work. But there’s no purpose, there’s no riverbanks, there’s no like guideposts. And that’s kind of where it was like, “Oh, well, we’re forgetting our values. We’re forgetting why we said ‘yes’ to this project or the job in the first place.” And then when we don’t remember why we said, “Yes.” And we also don’t have riverbanks that guide our work. It just kind of it makes it messy. Give you an example.

Someone called me recently and said, “I think that I’m going to be leaving in the next six to nine months. I’m just tired. I think I’ve done my job and I’d want to know what you would suggest for me.” And I said, “Well, the first thing you need to do is get a big sticky paper and write out all of the things that you wanted to do when you first started this job. Start identifying the things that you’ve accomplished. And then what’s left? What are the things that you wish you wanted? That you really want to do.” And in that way, her next six to nine months can be so laser focused on two or three of those things so that when she leaves, she knows that she has done what she meant to do. And then it also sets up again, how does she want to be known as she leaves this, this next role?

Sundae: Yes, it’s such a different energy than, like, waiting it out. You know, if we take it from a globally mobile space, right? When you’re like, “Oh we have the next assignment, we’re leaving in 6 months,” you almost like check out energetically and emotionally. And you’re just like, you’re gone, you’re gone, you disconnect. And what you’re saying is, “No, that’s when you dig deep.”

Naomi: I think you can do both. I think you can dig deep. So to use the example of being a globally mobile person who has the next assignment coming, we do check out. And you start, you get your timeline that you use the last move and you start checking the boxes of what you need to do for the next role for the next location. But I think we are so resilient as humans. We can also dig deep in the place that we are currently. Going back to Jerry’s leaving well concept, there’s all of these like real time solutions that you can implement.

For us, when we’ve moved locations, we make sure that we go back to the favorite places. We make sure that we go back to say goodbye to our favorite wait staff. We make sure that we take photographs of the things that really matter to us. And so those things can also be applied to the leaving well concept in our careers, our professional lives.

I think also you know when you think about leaving a place, most often you have a relationship with the people that you work with or even a relationship to the outcomes that you were tasked with. And if you don’t say goodbye to those things and I think that sounds a little like, whoo. But if you don’t intentionally say, “Thank you.” Thanks for what you brought to me. Thank you for the opportunity to have this moment. This outcome, this work.” I think that it also doesn’t set us up for success in the thing. So, there’s a lot of reasons to leave well and make it a practice.

Sundae: Yeah. And I think it would absolutely change the quality of your weeks, right? Instead of being bogged down by like the operational demands, it adds another layer. And what I’m hearing is when you’re living in alignment with your values and you have personal purpose and meaning in what you’re doing, it changes how you engage in your operational day-to-day.

Naomi: Well and think about too, the difference between if you imagine a typical office setting. I know folks are doing remote and people are doing virtual work now. But if you think of a typical office setting where traditionally people are sharing the same space, think of the outright difference between someone who has checked out and has another 30 or 60 days, versus someone who’s coming in and saying, “I have this much time left. What can we do today? How can I help you today? To make sure that you have what you need.” It just shifts everything. And not only that but it becomes this really beautiful opportunity for modeling behavior and then the ripple effect of leaving well with the folks that stay, whether they know it or not they’ll pick up on that same energy. It also helps them welcome the next person in a much different way than if there hadn’t been intention. So it just becomes this really holistic and beautiful opportunity.

Sundae: Exactly. So what if you already have a leadership position and you haven’t thought forward. You’re like actually it’s a great idea, but where do I start?

Naomi: So I think it goes back to the values. I think there’s all sorts of places that you can get a list of common values. So I would encourage everyone to Google, list of values. It’ll pop up and you can spend some time circling the things that pop out to you in our really immediate values that you identify with and then pull the top three to four of them. And then that into a document, make it a living document. A Google doc or whatever you can use that, maybe it’s handwritten. But start to identify how those overlap and how you already see those in your day-to-day life.

So for me, one of mine is kindness. So if kindness is a value for me, am I bringing that to work every day? Am I bringing it to the way that I schedule a meeting? So for me, this sounds very, very rudimentary, but a kindness value for me lives out when I schedule a meeting, I make sure that I have a pre-read. So if you don’t already know about my organization, here’s a link in the calendar invite, and here’s the agenda that we’re going to talk about. And by the way, I only schedule for 45 minutes so that you have time for a bio break for your next.

So that seems like it’s like, “Oh, that would be lovely.” But it goes back to very intentionally. I’ve done it because of the kindness value is something that I want to live into. So what happens then is when I leave a project, if people say, “What would you say about Naomi?” “Oh she was kind, she only ever scheduled 45 minutes.” And I always remember that. So I think you can just take it bit by bit. Find those values that you identify with for your life and then start to see how you can attach them to your work.

The other thing I think I would say for someone who’s currently in a role and thinks, oh maybe there’s no time or it feels too hard of a slog. If you think about the things that you were excited about when he first took the role or when you first were asked to apply for the job. What were the things that were so exciting? Oftentimes, we lose those and they fall to the bottom of the pile because the day-to-day operations take over. So remembering those things and seeing, can you invite those things back? Can you invite the excitement back? What are the things that felt too big that someone told you you couldn’t accomplish and so you set those to the side? Revisit those, because those things can also be legacy.

One other thing I’ll say Sundae and this is a very practical set of advice. But the most beautiful way you can leave well is to set up a structure or framework so that those that come behind you don’t have to do so much work to keep it going. So, that’s another really practical thing you can do is start to lay out a framework of, where does someone find the things that I’ve put together? Where does someone find the frameworks that I’ve laid, so that that can be left behind as well?

Sundae: Mmm, so good and I wanted to just mention here, we’ve talked about an office, right, but there’s so many other ways that we lead whether its corporate context or in the community organization, a religious or spiritual community, that I think these ideas definitely apply beyond let’s say a corporate context, right?

Naomi: Yeah.

Sundae: I just think how much power this has to create more meaning in your everyday life, right?

Naomi: Well, and if you think about too, so you mentioned community organizing and that’s a really good example. Often times something will happen in our world or in our private spaces, or in our small communities, where we have a reaction to something. And I won’t name examples because they could, depending on your audience, people will have different reactions. But think of a thing that makes you react. You know, like, “Oh my gosh, we cannot have this in our community. I am going to go fight the good fight.” I can guarantee you that for everything that you have that visceral reaction to, someone has already been working on it. You’re not the first. And so the problem though is that the people that have been working on it before you maybe didn’t leave artifacts? Maybe they didn’t think the trail that you can go pick up on. And so, that’s another really beautiful way that we can step into and embody leadership in this leaving well, is that if you’re working on something, leave something behind. Leave the little breadcrumbs, leave an artifact of some sort that people can then pick up the mantle and then carry forward.

So I think that goes back to kind of that framework and the structure. Scaffolding almost if you will. And then this is leadership by preparation. I think comes into play when we think about our end-of-life planning and how well we can leave a legacy that way.

Sundae: My whole body just like shuts down when you start talking about that because I’m like, “Not going to happen.” Like I know I just completely go into like denial.

Naomi: I know. I know. And you know what I think. I think that for all of us as humans we have The most ability, we have the highest ability to attach when something’s happened to us. And so I did not fully understand how important this was until I was asked to manage my uncle’s estate. And it was like, “oh if only he had done…If only he had thought forward about his legacy.” Because part of his legacy could have been, “I’ve organized it for you all so that you are not having to scramble and argue and grieve.”

So that all you have to do as part of my legacy is grieve and remember. Shutting down is the natural reaction and itching into it just a little bit more to say, “Okay. It’s going to happen. What’s the small thing I can do to help protect that legacy?”

Sundae: I’m actually going to put a link to a podcast episode I did with an expert on estate planning to help keep this conversation going and to keep myself accountable. Because it is. It’s an act of love to prepare for your loved one’s. To take that he’s away. I’ve also been privy to what happens when you are responsible for the estate. And it’s like a second job for six months, right? So you work full-time during the day and then you go home at night and you do that for six months and that’s heavy, it’s heavy.

Naomi: It is heavy. And not only that, it goes back to that what are we asking others to do because we didn’t plan for our legacy? So it’s in the job space, it’s in our personal spaces, and it’s in that end-of-life space. So if I have not prepared for my kind of life, I’m asking my family to bear the brunt of that when all they should be doing is grieving and celebrating. In a professional space, if I haven’t prepared for my legacy, I’m asking others to pick up the slack for my absence, and their own jobs and prepare for the new person coming in. So there’s a way that we can bring in caretaking for each other, community care, and protecting our legacy and preparing for it.

Sundae: It makes me want to ask something kind of pragmatic. When someone’s going to leave an organization is actually nobody’s business until you make that decision, right? But once you do, and it’s officially communicated, a lot of people are implicated. What do you think about people being transparent about thinking about leaving before they’ve actually made that decision?

Naomi: So I’m glad you brought that up. So every time that I have managed a team, whether I’m the official manager, or I’m project managing I say right off of the bat endings are inevitable. So we are all going to leave. None of us, literally, none of us still have our first job. If that’s true and then we can say, “Well endings are inevitable, how can we plan now? So people get a little bit weirded out about this. But when I first come into a project team management situation, I say, “Let’s all get our resumes out. Have you updated it? Is your current work that you’re doing on your resume?” And they’re like, “Why would it be on my… I don’t have plans to leave.” But it’s in that very practical like, “Well, then let’s all stop and do that together. Let’s come back to the next meeting and make sure that we’ve updated our resumes.

And that’s just kind of lets everyone breathe a little bit easier. Like, “Oh, let’s all just get prepared together,” so it’s not this one sneaky suspicion that someone might be leaving. The other thing that I think is a really practical way to do it is to just talk about, in the US we call them SOPs, Standard Operating Procedures. A simple check of, what are the two top things that we should get on paper right now in case something happens to one of us? I think we can talk about it in that way too. It doesn’t have to be a transparency that I am planning on leaving. It can just be, we should protect the organization by making sure that if and when one of us leaves, we’ve got some things in place.

Having said that though, I do value for folks who can, I think there’s a lot of folks who are in working situations where they’re not safe to be transparent about their leaving. But there’s a way that you can word everything to say, like even just too say like, “Gosh, we’re all gonna end up leaving someday. So what is it that we could do today to best protect the organization.” And that doesn’t bring up any red flags, I don’t think, my to protect the organization. Of course, everyone would want to.

The other thing that I think that is really, really helpful is for managing leaders. So people who have people under their care to ask, “What is it about your job that you want to lean into more? What is it about your role that you’re not having growth opportunities?” And that can also start that conversation about what might be next. And I learned this when I was doing volunteering, I would raise my hand for everything, and not until I realized that if I sat on my hand, it gave someone else an opportunity. And so I think we could shift our thought process there. As well being in a position, we can outlive our positions and so someone may be else should come in, which makes it a little bit more natural to talk about leaving. Not a negative.

Sundae: Absolutely. I remember one of my leaders that I had years ago on my first day, he was like, “So for you to really make a contribution, I’d expect you to stay for two or three years.” It was just really liberating to hear, to have that conversation about expectations and open the door of, “You will probably move on one day,” right? And I appreciate that. I’ve had two people who have said that like, “For this to be worth it for us and for you, let’s try to commit to this timeframe.” And I think that’s nice.

Naomi: From a human resources, people perspective, it costs an organization so much money to have to fill a position. And so if there’s a little bit more transparency on the front end of like, “Let’s talk through.”

We’ve talked a lot about the leaders. Do you mind if we shift our attention a bit to the “Stayers?” So what do we need to know?

Naomi: Well, I think that there’s a feeling of abandonment and feeling of, I think it’s very easy for “Stayers” to feel it it’s personal. I think even if we look at it from a globally mobile perspective of changing postal codes and zip codes the “Stayers” often feel like they’ve been left behind. And so, I think that there’s really beautiful ways in a corporate or in a professional work setting to just acknowledge that that is true and it is normal to feel abandonment. I think there’s also a lot of times feelings come up of jealousy, and being kind of at a covetous space of like, “Why do they get to leave? And why am I stuck? Or why do I have to stay?”

So I think for “Stayers” I think the one thing that I would suggest is if those feelings especially of jealousy come up, what is it that’s keeping you from exploring? What might be next and what is it that’s keeping you from wanting to also protect and create your own legacy? Don’t make it a victim mentality. You can honor the feelings but then move right into doing the exact same thing. Identify your values. Do your value still align with your project or your role or your company that you’re with?

The other thing I would suggest and this is going to feel maybe not so great or effusive. But offer to the person who’s leaving, ask them what they need in order to help them leave well. Oftentimes it would be something like, “Can you help me build this framework? Can you help me capture and document the artifact?” And that also then becomes resume builder. If you’re the person that helped provide that structure, if you’re the person that helped bridge that transition that also helps if you want to stay in the future of your organization. If you’re the one that helped create stability, make sure that that’s known. Step into that space.

The other thing, I think that’s really important for “Stayers” is to just be present, notice, and listen. There’s a lot of trauma that comes with transition even when it’s done well. And I think for folks that stay behind, listen for the opportunities where you can provide support to each other, be present about how you’re feeling, and how you’re showing up. And then I guess I would just say again, it’s an opportunity to check in with your values and make sure that they’re still aligned.

Sundae: Right? Exactly, that’s great. And honestly, it’s so obvious when I hear it now, but I don’t know if people are using that same transition lens.

Naomi. I don’t think so. No, I don’t think so. But it comes back to your question like, where did that come from that we assume that loyalty is the kingpin of what we are signing up for when we take a job or a role or a project? I think about there’s another example I can give, I was volunteering for a women’s circle is the easiest way to explain it. I was in a president role and you serve for two years. Well, I knew a year ago that I needed to be done. And so I could have either stuck it out, slogged for it, counting down the days. Almost like, remember making paper chains–

Sundae: Yes for Christmas.

Naomi: Yes could have had like a chain probably of like, “One more day done. Thank goodness.” Or I could make the paper chain and on each one of them have something that I wanted to intentionally do that day. So I did that and I laid out the year and I dug in really, really deeply on:

  • How did I want the remaining leadership team to feel when I left?
  • How did I want them to feel on my last meeting?

Then I backed that out. So if the outcome was this:

  • How do I want to feel?
  • How do I want them to feel?

Then I backed it out over the course of time that I had and then it became really, really practical small little things every day that led up to and connected to a really good leaving well.

Sundae: I mean these are all very familiar coaching practices of like creating the visualization of it and then working back and checking in, the accountability and it actually doesn’t take that much time.

Naomi: It doesn’t take that much time. And I think one thing that might be helpful for anyone listening is the common response I get is, “But my boss would never go for this.” Or, ”It’s going to feel weird if I suggest this.” You just have to do it anyway. So I think what I would suggest, any time you have a concept that you can name, it makes other people curious or it lets people kind of embrace it. So it literally physically say, “I would like to try practicing leaving well. And what that means for me is…” and then you fill in the blank. I guarantee you that there’s going to be some interest and some intrigue, and some curiosity. At the very minimum, they’ll be like, “Okay, cool, whatever.” They’ll be like, “Sure, you do what you need to do.” And then just naming things signaling that out lets people start to adopt it and before you know it, they’ll also start to be intrigued by it. And they’ll be ready to kind of come alongside you, link arms with you, and the leaving well process.

I left a job a couple of years ago and I said, every time, “As I leave, I want to make sure I leave well. As I leave, I want to make sure I leave well. As I exit, I want to make sure that you felt that I’ve left well.” And just you know, the boss who is still there calls me on a regular basis and says, “You know someone else just left and they left well.” So we remember, right? And so if you just name it and speak it, it’ll be a lot easier for other people to come along.

There’s also some books and some recommendations of ways that you can kind of inject it, Necessary Endings by Dr. Henry Cloud is a fabulous book. The First 90 Days. The button up summary is when you’re intentional about how you leave you are setting yourself up to not only enter the next thing well, but you’re also creating a ripple effect for those that stay behind.

Sundae: Well, and there’s a couple of the things I keep going back to purpose and meaning, it just seems so much more meaningful and that is rewarding for everybody. The other thing is, it doesn’t take very much time. It’s literally just this intention 20 minutes here, half an hour there to get clear.

Naomi: And I think about from a hiring organization’s perspective as well, they want good apples, if you think of the bad apples ruin the whole entire barrel concept, they want good apples to leave because that reflects back on their organization. So, if I’ve left well and if my organization as allowed me to leave well, I will likely talk about that organization in much higher terms and in much more glowing ways than if I hadn’t left well. And so, it’s really in everyone’s best interest to practice, and it’s a practice. It has to be formed.

And the other thing too is there’s no one way to do it. It’s going to look different for everyone but I think you hit the nail on the head when you said it doesn’t take that much time.

Sundae: I just why aren’t we doing the things that will make such an impact that are so light. And it’s also not expensive, you can do some of these reflections on your own. Yes, you can work with a coach, but it’s about intentionality.

Naomi: Maybe it’s a list of passwords, maybe it’s a list of the things that I didn’t get done yet. But here’s the framework that I started. So there’s all sorts of ways that you can set yourself up to with having a list to reflect on that also doesn’t cost much money.

Sundae: I just think about often when we come into a new position, we’re very focused on understanding the organization delivering. And we don’t go on the mental level. So, I think it’s wonderful. This conversation, I’m just thinking about intentionality, I’m thinking about values. How can we talk about knowing– How do I know when it’s time to go?

Naomi: Yeah, so it’s going to be uniquely personal for everybody, but if we lean into our intuition in our gut, we all know. We all know when there’s something that doesn’t quite align anymore, and I will be really intentional in saying, non-alignment isn’t always icky. It’s not always something that feels terrible or is negative or feels tiresome. Sometimes a non-alignment is either a calling to something else. I wouldn’t say a higher thing, but It’s a calling to something else or just a natural shift in organization as it has different leadership in place. Or as it has a null say leadership by title or as their mission shifts. It might just be that you start pulling away.

So I think that often we assume that a no longer fit is bad. No longer fit can also be really, really empowering and really beautiful. If we are so aligned with what our values are, we will know. And when you know, I think that’s an opportunity to go back to whatever your self-care or whatever your personal wellbeing things are. Whether it’s journaling, time with friends, time outside. Ratchet that up a notch. If you have that feeling of knowing that it’s time, spend some self-awareness time to check in.

The other thing that I think is not often talked about is sometimes it’s time to go and we know because someone else is a better fit. If you have someone that reports to you or that works with you, that you see might be a better fit for what you’re working on. That’s also a really, really incredible leadership opportunity to say, “Maybe it’s this person.” And that’s an opportunity to have really, really beautiful leaving well conversations inside of your organization or project. To say, “I want to maybe flag that this person would be great for this role.” That’s a powerful leaving well opportunity, if you know.

Sundae: Yeah, absolutely. And I also just want to use this opportunity to also say thank you to you when I was in a transition with my community, right? With my podcast. I wasn’t leaving anybody. But I was leaving one sort of scope and moving into the other and that’s what you and I talked about during that time is processing, like, how do I feel about that? It wasn’t a misalignment, it was just a shift, a shift. And then, how do I do that? And how do I do that intentionally and with care? And so, that I’ve had your support on that process and I know how much that helped with that transition.

So we’ve talked about it from like it organizational perspective. And I would even say that’s valuable within your own business, right? If you’re shifting even your niche or who you work with those same principles also apply.

Sundae: Do you mind if we turn the attention to you a little bit, you’ve given us so much on these concepts of leaving well and being good “Stayers.” Also, how an organization can really nurture that process. But I want to know a little bit about your own process right now. Now that I have Ambitious Transformation in Transition, do you mind telling us a little bit about what is in transition for you right now? What? Which ones are you feeling? Yeah, so say more.

Naomi: So transformation that I’m currently experiencing. So in my personal life, we have just moved, we moved from a two household situation, and combined our households back into one location. So that’s been an interesting transition. I’m also In the process of leaving employment to go to a contract position. So I’m changing the legal status of how I interact with my work and it’s interesting because that felt like not a big deal. It’s just a legal status, I’m no longer an employee, I’ll be a contractor but it has caused or has given me an opportunity to really lean into practicing leaving well, because I’m leaving a team behind. They feel that they’re being left behind in a certain way. And so, It’s been a beautiful way to practice that transition.

I’m also working towards a transition of just literally how I live my life. You brought up the concept of ease before and ease is something that I am chasing so so valiantly. I want my mornings to be full of ease. I want my decisions to be more at ease. And it goes back to the values and riverbanks. If I know that this is what I stand for or this is the work that I want to do, it makes the “nos” so much easier, and there’s so many other people out there who can do the work that I say no to. So, that’s a transition for me. When I reflect back, I’ve lived a lot of my life in chaos and franticness and fast-paced. Need to do it all need to have it all and I’m really pushing all of that to the side. So that’s been a transition that will be ongoing. I know it will be a journey but I’m inviting welcoming and chasing ease.

Sundae: I’ve watched you live that. I’ve watched, you have all of the things. All of the good things but then make choices make tough choices to get to where you’re at right now. So what is ambitious for you right now? As you know, I define ambitious as has to be outside of scope or scale of any sort of definition. It has to come from you. So what is ambitious for you?

Naomi: So what’s the first thing I thought of when you said that about what’s ambitious, I’m writing a book, and while that might not seem super ambitious.

Sundae: Are you kidding me?

Naomi: I mean, I write. And so like you know, if anyone who’s a blog writer or constantly is in writing spaces to write a book, it seemed initially to me like, “Oh, I yeah, I’ll do that.” But what I’m finding is that because it is part memoir, there’s a lot of healing that is going to take place that I wasn’t prepared for. I’m also going to combine the tarot, the major arcana with this book. And so there’s a lot of research that I’m not accustomed to. I’ve always written kind of from the heart and from the hip.

And so the ambitious piece is coming in needing to really plug into doing right by this book. And I think that feels ambitious to me to lean into the hard and lean into what doesn’t come naturally. So that I can put out this thing and do right by it.

Sundae: That’s so exciting. I can’t wait to hear more.

Naomi: So well I printed I printed the manuscript someone said, “Do not let it just live digitally. You need to print the manuscript and hold it.” And oh my goodness. That was a huge shift.

Sundae: Oh, I bet that felt amazing too.

Naomi: It felt amazing and terrifying too.

Sundae: Well, you have to keep us posted on that. And we will put links to all of your spaces and places, and please come back to us when the book is live so that we can also include that their. You have so much to offer Naomi. And I get all teary when I talk about it now. But you know, I met You in 2018 and in person, although I knew of you before. And you have always, of course, you’re talking about leadership, you came talking about community before. You’ve just lived all of these principles so fully and so future-oriented, that’s something I’ve always respected about you. And you do the right things, even though they’re the hard things. And that’s something I really appreciate. And it’s so interesting that you bring in ease in the heart, if that makes sense. Like you do already bring in ease, at least four others. That’s something you see you do all the time. So you being a role model for this, you living that also sets a path for other people and you’ve been laying that path for me and many moments of my own life and I just wanted to say thank you. Because I don’t know if you realize how much of an impact that’s made.

Naomi: Thank you.


Sundae: So thank you. I did that without getting to teary. All right, so I think it’s about time, we have to close up here. I think we need to talk about this more. I think we can look at where we’re leaders in our life and apply that immediately. I think as “Stayers” we also have agency. Even if the leader doesn’t want to leave well, we can also do that. And I am just so grateful. So thank you everyone for listening to IN TRANSIT with Sundae Bean. Always a pleasure to have you here with me. I’ll leave you with the words of Tim McGraw: “We all take different paths in life, but no matter where we go, we take a little of each other everywhere.”

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The post 297: Legacy by Design with Naomi Hattaway appeared first on Sundae Schneider-Bean, LLC..

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