I Don't Know How You Do It

How to Baby Step Your Way to Your Dream, with Tanya Hackney

August 22, 2023 Jessica Fein Season 1 Episode 31
I Don't Know How You Do It
How to Baby Step Your Way to Your Dream, with Tanya Hackney
Show Notes Transcript

Have you followed the conventional path -- school, marriage, kids, job (maybe not in that order) and found that you life doesn't really align with your dreams? Have you been told that following the conventional path is the only way to find fulfillment, only to be left feeling unsatisfied? Maybe you look at other people and wonder how they're able to throw expectations to the wind and set off on grand adventures.

My special guest is Tanya Hackney

Tanya  went from living a life built around societal expectations to taking the path less traveled. Tanya, with her husband and five young children, decided to break free from the constraints of suburbia. They traded their conventional life in the city for an adventure at sea, living aboard a boat for a decade. Tanya's expertise as a former elementary school educator came in handy as she successfully homeschooled her five children amidst the rhythm of tides and sails. Returning to 'normal life' a decade later, she has encapsulated her unique journey in her book "Leaving the Safe Harbor."

We baby stepped our way out of suburbia and into a little house in Florida and onto a little boat that we could practice on. And my husband baby stepped out of a brick and mortar career into working from home, which eventually led to him becoming a digital nomad. I had quit teaching so that I could stay home with the kids, but my natural next baby step was to homeschool. - Tanya Hackney

In this episode, you'll learn:

  • What it means to baby step into your dreams
  • How to coach yourself through audacious goals
  • Why you need to find alone time, and how to do it
  • Why you shouldn't postpone your dreams
  • How to collect verbs instead of nouns

Learn more about Tanya:

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Music credit: Limitless by Bells


Jessica Fein: [00:00:00] Welcome. I'm Jessica Fein, and this is the I Don't Know How You Do It podcast, where we talk to people whose lives seem unimaginable from the outside and dive into how they're able to do things that look undoable.

I'm so glad you're joining me on this journey, and I hope you enjoy the conversation. 

Welcome back to the show. Before we get into today's episode, I just wanted to take a second to thank you for listening. I know there are so many podcasts out there. And you have a ton of choices of what to listen to.

I'm really glad that you've chosen to join me on this journey and to be part of the community. Now, on to today's show. My guest today is Tanya Hackney. Tanya and her husband were a couple of average high school sweethearts from middle class America who went off to college, got married, followed all the rules, played it safe, and pursued the American dream.

But then they found that they felt boxed in by their predictable life, and they wanted some adventure. They decided to revisit the dreams of their [00:01:00] youth, abandon the conventional path, and leave the safety of suburbia to live aboard a sailboat with five children. They lived at sea for 10 years, which Tanya documents in her book, “Leaving the Safe Harbor.”

Tanya talks about the trade offs of prioritizing relationships and experiences over material things and a so called normal life, and what it's like to homeschool five kids at sea in very close quarters. And also what it's like to return to a quote unquote normal life 10 years later. Without further ado, I bring you Tanya.

Welcome Tanya. I am so glad to have you on the show.

Tanya Hackney: Thank you so much. I'm really looking forward to this conversation. 

Jessica Fein: Can you just describe where you are right now while we're recording? 

Tanya Hackney: Sure. I am sitting in my cabin on my 48 foot catamaran. It is a sailboat [00:02:00] that I have lived aboard for 15 years. With my family, I raised five children aboard this boat.

It started a really long time ago. My husband and I were high school sweethearts. The summer that we fell in love, he was sanding the bottom of his dad's boat. And so he had grown up sailing. And when we were newlyweds, we took a trip in his dad's boat with his dad and stepmom out to the Dry Tortugas, which is a national park west of Key West, like way out in the middle of nowhere, and requires that you be out of sight of land.

And so we took this sailing trip. And it was a really amazing trip. It was kind of represented all the highs and lows of sailing. It started with a storm at sea. If it had ended with a storm at sea, my whole story might be different, but it started with a storm at sea on the way there. And then on the way back, it was like an overnight sail on in calm waters with a million stars in the sky and phosphorescence in the water.

And it was so magical. And I thought. This, let's just do this instead of all the normal things that we [00:03:00] wanted to do. And so we actually did the normal thing for a while. We were sort of suburbanites with 2. 5 kids and house with the white picket fence and weekend car. And we kind of rejected all of that, did a U turn, left Atlanta, came back to Florida, bought a sailboat and moved aboard with four children under the age of eight.

Jessica Fein: Okay, well, you make it sound so like, so we did that and we rejected that and we had four kids and we were like, great, let's just go on the boat. So first of all, what was life like before the boat and what made you say not, hey, let's go on a two week vacation, but let's give up everything we've worked hard to establish.

I mean, you said you had the yuppie lifestyle. What did that look like and why wasn't that working for you?

Tanya Hackney: Right. Well, I gave it to you in a nutshell. Obviously, it was much longer, harder, and, you know, more laborious. We had this big idea, but we did not know how to execute. We had been, you know, brought up in this system that you go to school, you go to college, you get a job, you get married, you have kids, you buy a house, [00:04:00] and, you know, maybe not in that particular order, but...

You know, then you work your whole life and then you retire, then you travel. That's kind of like the formula. It was very, very hard because what we were rejecting was sort of some programming. We started out doing the normal thing where you go to high school, then you graduate and you go to college and then you get a job and you get married and buy a house and have kids and you to follow that formula.

And then eventually you work really hard and you take a couple of vacations and you retire and you travel when you’re retired. And that's kind of  The American Dream, and we had it. We didn't really like it, but we weren't sure what to do differently. And so I was an elementary school teacher in Atlanta, and my husband was a computer consultant.

We had started out our marriage deeply in debt, like $50,000 school debt and car debt and personal debt, which is actually part and parcel with the American dream. As we started looking around at the people in our little neighborhood once we bought our first house, we realized that that whole keeping up [00:05:00] with the Joneses lifestyle that we were in, Involved being deeply in debt and we didn't like it.

And so we ended up paying off all of our debt. And that was probably the first step that we took towards our freedom. We started talking about selling the house when I was pregnant with our third child. It was really hard to break free. Everything in your culture, in your society says, stay where you are, or maybe buy a, you know, a bigger house and a bigger car, but keep filling your 401k.

Don't rock the boat. Don't do anything. Extreme, make sure that you live in a neighborhood where there's a good school for your kids, you know, there's sort of a track and we got out of the beaten track and it was hard because people criticize you and think that you're crazy and ask you difficult questions that you can't really answer because aren't you leaving a safe life for something dangerous?

And the answer is yes, yes, you are choosing danger. And why would you do that?

Jessica Fein: So people are saying, why are you doing this? And of [00:06:00] course there's probably a little bit of like, why are they brave enough to do it and we are not. But I'm curious. So you have these jobs, you have the kids, you have the house and the white picket fence.

You even have a fancy car to drive around with on the weekends. Which one of you was like, uh, hon, we need to talk. There's something I want to suggest. Like how did that even come up? And did one of you have to convince the other?

Tanya Hackney: That is a perfect question because a lot of it is about our relationship. I mean, you couldn't do this on your own.

What we did, we could not have done. I mean, we've seen families where the dad wants to go on an adventure and the mom's just on it, you know, to satisfy him. And it's. It's almost impossible. We also find a lot of sailors that are newly single, where they've gone out sailing and this spouse has flown back home.

So we definitely needed to be, you know, on board together. So we actually went looking for a house. We went looking for a, a second house. We were pregnant with our third child. And the whole time that we had been living in Atlanta, my husband had been racing sailboats on Lake Lanier on [00:07:00] Wednesday nights.

We read Cruising World magazine and Sailing magazine, and we were always talking about this thing that we wanted to do. And we both really wanted it pretty much ever since we had gone on that trip with his parents as newlyweds. It was something that we just talked about, like pie in the sky. Probably everybody has a thing that they talk about.

This is not... We have a thing. Right. This is not abnormal to dream. It's a human universal trait. I think what's abnormal... Is to actually do it because mostly our dreams are, they look insane. Like who could even do that? Who could even get up in the morning and wake up in an exotic location on their sailboat and homeschool their kids while the back of their boat hangs out over a reef.

Not many people actually do the thing because. Quite frankly involves a lot of risk and it is a little crazy. It is. 

Jessica Fein: So how'd you go from we're looking for our second house to forget the house, the house is going to be a boat?

Tanya Hackney: Yeah. So we found a house. We found [00:08:00] this great starter home. The real estate broker was also a mortgage broker.

So he sent us home with paperwork and he's like, this deal's as good as done. You sign this one piece of paper and we can get the ball rolling. And we came home with paperwork and we were supposed to sign it and bring it back Monday. And by Sunday afternoon, Both of us had said to each other in one way or another, very tentatively, we were like, I don't think that this is the right thing to do and the other person was like, Oh, thank God. I don't think this is the right thing to do either. I'm so glad you said that. I personally thought that it was a trap. It was, you know, the shiny new thing. It was a little too perfect. And I knew that if we bought that house that we might never try our crazy dream.

And I thought that we should at least try. Maybe we wouldn't succeed. We had no idea back then what it entailed. And if someone had told me what it entailed, I would not have done it. I would have bought the suburban house. So it's probably a good thing that we didn't know how hard it was. But we knew that we would have regret.

We had plenty of fears about going sailing [00:09:00] with small children. We had really never done it. We'd never even owned a boat, let alone taken a kid sailing or moved aboard a boat. But there was this other fear of the fear that we would die with regret, that we would get to the end of our life and wish that we had lived a little more fully.

That really drives a lot of my decision making is what am I going to say on my deathbed? It's not really morbid thinking. It actually makes me live more fully. 

Jessica Fein: That's a great way to make a decision. My sister used to tell me when I was deciding between two things, which one will you have bigger regrets about?

And it was a really good way to help me focus in on what might feel like the scarier choice, but also the choice that I should go for.

Tanya Hackney: My kids know this about me. That's how they got me to go ziplining. I was actually all fully harnessed and I'm standing in the top of a rainforest tree in Bocas del Toro, Panama.

And I'm like, why would a person jump out of a perfectly good tree? It's like 200 feet off the forest floor, like, I don't really want to do this. And they were like, yeah, but what are you going to [00:10:00] say on your deathbed? Are you going to say, I wish I hadn't taken off all that gear and walked back through the forest?

Or am I going to say, I wish that I had leaped through the tree? And I'm like, oh, you guys. 

Jessica Fein: Okay, remember Family Feud? My family was chosen to go on family feud and this was a really long time ago. We were all set to go, you know, we had the plane tickets, we had the everything, we were going to be on family feud and then 9 11 happened.

And I was really afraid to fly after that. So I ended up saying like, I'm out. And you can't be on Family Feud unless the exact people who have auditioned are actually the ones. And I was the team captain, you know, anyway, I digress. But the point is that I was afraid to fly for a little while after that.

And I was like, we're not going on Family Feud. And we didn't. And looking back, like pretty soon after that, I was like, we should have gone on Family Feud, you know, we would have won. It would have been fun. Who knows? Literally, I still think about that. And yeah, you know how long ago it was, but I still think about that.

Like do the thing, [00:11:00] right? 

Tanya Hackney: Do the thing. Even if you're afraid, I say do it, even if you're afraid, do it. 

Jessica Fein: Yeah. Sometimes, even especially if you're afraid, you know?

Tanya Hackney: I do a lot of things and I still feel afraid. I do it anyway. 

Jessica Fein: Okay, so when you've made this decision, now you're leaving everything behind, your neighbors are like, why you and not me?

But that's not exactly how they're saying it. They're just like, what are you thinking? How old were your kids at that point?

Tanya Hackney: So the day that we left Atlanta was my son's third birthday. I had a three year old, a two year old, and a newborn. My daughter was three months old. 

Jessica Fein: Okay, so you were in the house with the white picket fence and you had the three year old, the two year old, and the newborn, that would be really, really hard and chaotic.

And that's on land.

Tanya Hackney: It was. It was. 

Jessica Fein: So what in the world happened when all of a sudden you got on a boat and you've never even owned a boat before, now you're on a boat with the three, two, and newborn?

Tanya Hackney: So there were some baby steps. We didn't just go like house in the city straight to the sailboat. We made a five year plan.

We're very [00:12:00] reasonable people in the same way that we made a plan to get out of debt. We made a plan to get out of a house. And so we made a five year plan. We moved to a smaller house. In Florida, which required us to sell a lot of our stuff in Atlanta. So we did a, an initial downsize. We went back to Florida so that we would be near the water and near our families so that we would have a support system.

So we baby stepped our way out of suburbia and into a little house in Florida and onto a little boat that we could practice on. And my husband baby stepped out of a brick and mortar career into working from home, which eventually led to him becoming a digital nomad. I had quit teaching so that I could stay home with the kids, but my natural next baby step was to homeschool.

We were able to have some consistency, internal consistency, even though the external things were changing. And so we baby stepped into homeschooling, boat ownership, adventure, little by little. And when the time came, when we found the boat that would be our, well, I'm going to [00:13:00] call it our forever home, but it's very fragile.

Obviously, it could sink, anything could happen, but it's the longest place I've ever lived anywhere. We had baby stepped our way right up to that scary threshold. 

Jessica Fein: I like the idea of baby stepping because kind of jumping off, we were talking about going towards your fear, but that's like terror, right? And so now you were going towards your fear, but doing it in what seems like a really manageable way.

Tanya Hackney: There's a way that you coach yourself through that situation, too. So we had looked at this other boat, this Tiana 55, which is a big fiberglass, ginormous boat, and somebody was selling it and it was in really bad shape. And we had gone aboard to look at it. And so we had begun the process of looking and thinking about things.

And we hesitated, and someone else bought that boat and sailed it away. And I knew the feeling of regret of, Oh my gosh, we just let our dream sail away. We may never get another chance. And then when take two came up for sale, my husband found it on the internet and he's like, I think I [00:14:00] found the boat for us.

And he was. You know, like 97% sure. I'm like, are you sure? I don't want to get my hopes up for nothing. And then we start to realize what we're doing. Like we're going to buy a 48 foot catamaran. We don't even know if anyone will sell us a 48 foot catamaran or insure it, or you know, anything, or where we're even going to put it.

We, where do you find a dock for about that big, but we started with the swarming questions and we said, okay, well, all we have to do today. Is get in the car and drive to Fort Lauderdale and look at the boat. We don't have to answer all of those other questions. And so we coach ourselves through decision making by saying, what's the tiny decision that we need to make today?

Today, we just get in the car and drive to Fort Lauderdale. Anybody can get in a car and drive to Fort Lauderdale. That's no big deal. And then pretty soon you're standing on the dock and you're looking at the boat and you're like, well, anybody can call a bank and ask if they'll loan you the money for the, this giant boat.

Anybody can just call the bank. And then eventually, you know, you're signing paperwork and you're like, okay, not anybody can move aboard with four children, but we can [00:15:00] do this. You know, you, you kind of coach yourself into that till you can take that final step. The final step is still a leap of faith and it's still terrifying, I can tell you.

And then suddenly you're boat owners and you have four children under the age of eight and they think that this thing is a giant playground and I just remember the tour that my husband gave the kids when the boat finally came back to the dock. We found a dock for it in Bradenton, Florida. And my husband was like, this is a Seacock.

Don't touch it. This is the AC panel with all the electrical switches. Don't touch it. This is a fire extinguisher. Don't touch it. This is the engine kill switch. Don't touch it. And that was the whole tour . 

Jessica Fein: Oh my goodness. These kids under eight were probably like, I'm gonna touch everything. I mean, okay, so now you're on the boat.

You've got these four kids under age eight. First of all, what does it even look like on the boat? Where's everybody sleeping? There are six of you. Do the four kids all sleep together? I mean, what, how does this work?

Tanya Hackney: So it's a, it's a catamaran and so [00:16:00] it has two halls and then there's a main cabin in, we call it the upstairs, up above.

And so down below you have, two cabins in each hull, and they sleep, it's basically a full size bed up off the ground. It's a bunk, but it's, it's a full size bed, takes standard full size sheets. And so the, the boat sleeps eight comfortably. And then we later had a baby and built a fifth birth into a, what would have been like a couch, I guess, downstairs.

Jessica Fein: Wait, you had baby number five. 

Tanya Hackney: Yes. I know we didn't get there yet in the story. 

Jessica Fein: All right. Wait a second. How long were you on the boat before baby number five comes along?

Tanya Hackney: We bought the boat in 2008. We moved aboard full time in 2009. It took us a year of baby steps to get the boat. Like, family friendly, where you could have a toddler crawling around.

We had to put the battery switches somewhere else because you realize that, like, the toddler turned the batteries off one time, or it would be raining and the hatches would be leaking and we'd had, like, buckets and pots under the hatches collecting rainwater, and then my [00:17:00] toddler would come around and dump the water because he thought it was funny.

Jessica Fein: But you're talking about baby proofing, and I'm thinking, okay, there's one thing to think about baby proofing, like, you don't want your kid to put the finger in the outlet. But baby proofing, weren't you afraid that one of your kids was going to go overboard?

Tanya Hackney: Yes, absolutely. That's probably like the number one fear when you buy a boat.

It's the number one thing that the grandparents say like, well, what about sharks, pirates, drowning, shipwreck? Those are the kind of big fears. So all of our kids swam really well. That was one of our actually prime directives when we bought the house. In Florida was get the kids really comfortable with water, get them so that they could, if they fell in, save themselves now in the ocean.

If we're sailing, they know how scary that is. Nobody's going overboard and certainly not without a life jacket. But the first rule of falling overboard is don't fall overboard. We had this coconut game where we would be out sailing and we would see a coconut floating and we'd say, okay, keep your eyes on that coconut.

Keep your eyes on the coconut. Just watch it. And then you would try to distract the kids. And then you'd be like, where's the coconut? And you're [00:18:00] looking even in small waves. And that thing just disappears. I'm like, okay, not to scare you, but that could be your head. If you fall overboard, that's like the size of your head.

How are we going to find you? So when we say, ask us to leave the cockpit, ask to go forward, hold on, you know, there's one hand for you and one hand for the boat. When we say those things, it's because it's life or death, and they understood that.

Jessica Fein: But how did they understand that as toddlers? I mean, as little ones?

Tanya Hackney: So, that was the hardest part. The hardest part, I think, is between, like, nine months and a year and a half, where they're mobile, crawling and things like that, but they're not old enough to understand. You know, you can't put the fear of God into them. So you teach emergency swimming. So my toddler swam, he was diving for pennies at two and a half.

We were at the Marina, at the dock, wearing life jackets on the dock, wearing life jackets if he was up on deck. So if he had fallen in, you know, the rescue protocols, you actually really have to watch a toddler and keep an eye on them. You know, there are consequences. You can't just have rules. You also have to have [00:19:00] consequences.

So, you know, if he were to crawl. out of the cockpit, which is enclosed, and crawl onto deck. That would be the end of outside play. You have to come back inside. And so they learned the safety things. It wasn't just, don't go down by the water. It was, don't leave this cockpit without permission. And that rule was established early on and was strictly enforced.

But then we would go up to the marina pool and practice swimming every single day. And by the time he was two and a half, he could, he could go down to the bottom and pick up pennies off the bottom, which was fine during the week. You know, we were home homeschooling. No one was there. But on the weekend, all these weekend boat people come down to the pool and they're hanging out by the pool and they're like, Oh my God, there's a toddler drowning in the deep end.

And I'm like, no, no, no, no. He's just diving for pennies, you know, and he was so tiny, but he swam really, really well. And then with children smaller than that, you can actually teach emergency swimming techniques to say, you know, to save themselves. Babies actually know how to swim. Everybody remembers that Nirvana album cover with the baby swimming.

You know what I'm saying? [00:20:00] But that is really what babies do. Babies know how to swim and they're chunky and they float. You can teach a baby to float like a starfish. 

Jessica Fein: So you've got these five little kids and you are now setting off for what turns out to be 10 years at sea. And there's a set of challenges around having five little kids as we're talking about, you know, really thinking about safety issues.

But I imagine that the challenges morph and continue to evolve as the kids get older. For example, first of all, like, how many bathrooms are on this boat? 

Tanya Hackney: When we first bought the boat, it was a single hand pumped saltwater toilet. And that was a challenge. Obviously, a huge challenge for six people to be sharing one head.

It was not great. And then when we got pregnant with Rachel, I insisted that we open up another head. The boat originally was four beds and four heads, but nobody really wants four toilets. 

Jessica Fein: And what about alone time? I mean, your kids are getting older. First of all, they must want some privacy. But equally important, how do you and your husband get any privacy?

Tanya Hackney: [00:21:00] Privacy on a boat is a little bit of a myth because of the sound traveling issue. Like, it's very hard to get out of earshot of another human being. You're always kind of in a small space. So it's very hard to get private time. We became very disciplined about things like bedtime, so that would be how we got some alone time.

Or we would do date nights, even if we couldn't get off the boat, um, we would put a, a movie on or something. We'd set a laptop up at the dinner table. We would go outside, shut the sliding glass door, and have a romantic dinner outside in the cockpit. 

Jessica Fein: And what about alone time for you, or for your husband, or for one of the kids?

I mean, with the chaos of a big family, again, even behind the white picket fence. Each individual needs some time to herself. How did you find that? 

Tanya Hackney: Your podcast is about people saying like, how did you even do that? This is a big part of how I did it. So I have a very strict morning routine. I'm not a morning person per se, but I've always gotten up earlier than my kids.

Or even if they got up at the same time, I would go find a [00:22:00] quiet place. I would go sit in the captain's chair. My faith has gotten me through a lot of things. I get up in the morning and I pray and I. Sometimes exercise, you know, do yoga or something first thing in the morning, write in my journal, go outside, breathe some fresh air, look at the sunrise, whatever, that inviolable morning routine really helped me as a human being stay sane when things were really crazy.

And then my husband and I had a routine where we would go sit and watch the sunset together and the kids could come out and not ask us questions. We would say, Okay, well, we're having mom and dad time right now. Just hold on to your question. You can ask us and, you know, as soon as the sun goes down or as soon as this drink is gone, that's The routine that we had set up.

So we'd set up time for this. Um, my husband and I each took one night off a week. We started that when the kids were little, he was doing the racing on Lake Lanier. And I would go to Starbucks with my laptop and write because I was always a writer. Once we started traveling, that didn't happen. Then when I needed alone time, I would get into the uh, hammock. That was kind [00:23:00] of the mom space and I would not take any questions or comments while I was in the hammock. I'd be like, 20 minutes. I'll see you in 20 minutes. And I would set a timer and I'd say, you can ask me any question you want in 20 minutes. And I would go sit in the car in the A hammock with a book.

The best thing is the kayak. I love my kayak. When I felt like I was losing it, I would be like, I'm going for a quick kayak, and I would drop the kayak in the water and paddle off. And by the time I came back, whatever I was upset about or sad or frustrated or angry, all of those feelings would have dissolved and I'd come back and be able to deal with things reasonably.

Jessica Fein: It seems to me like this is the kind of thing that little kids might think this is the greatest thing ever, we're so lucky, and you know, this is all they've ever known, and so I can see how this would be just magical for little kids, but as they grew up, did any one of them ever come to you and say, hey guys, we've had enough, can we go have a quote unquote normal life?

Tanya Hackney: Yeah, actually, they probably don't know how great it was. I think it took a [00:24:00] long time for them to get some perspective because it was the only thing that they had ever known, living on a boat, doing boat chores, taking the dinghy ashore to get groceries or to do laundry or, or even like hanging the laundry on the lifelines.

All of those things were very normal. Homeschooling was normal. All the kids that they met while we were sailing, and we met lots and lots of other families doing this. All lived the same way that they lived, you know, you finish your schoolwork after lunch, you get in the dinghy and you dinghy across or you kayak over to a friend's boat and you knock and see if they're done with their schoolwork and then, you know, you go snorkeling or you go to the beach or you play games or whatever.

That was normal for them. January 2017 to January 2018. We lived in Panama and we were sitting at Shelter Bay Marina and all these people are getting ready to cross the Pacific. It's kind of the marina where you fix your boat and supply. You find your line handlers and you get ready to go through the canal.

And all of these people were getting ready to go and I'm like, Hey, you guys want to cross the Pacific? Let's go. [00:25:00] Let's let's go to Tahiti. Let's go to French Polynesia. And I was really excited about it. And then that's where there was a hard stop. So at that point, we had teenagers. They had been on the boat for a long time.

I think eight years at that point. And my oldest was like, If you guys decide to cross the Pacific, I'm going back home to live with a grandparent. I do not want to go like that was the level of. of no. And then my daughter, who was 13 or 14 at the time, was beginning to really miss having close friends.

And we had been traveling with another family extensively through the Eastern Caribbean that had two girls and they became very, very close friends. And my daughter seemed to always find other girls her own age, which was great. But the constantly like meeting up with people and then sailing away and then meeting up and then sailing away is really hard.

And it's harder for some people than others. And she's kind of an introvert. So she would get close with somebody. And then we would sail away and this was really taking a toll on her socially. And so she also was like, no way, I do not want to cross [00:26:00] the Pacific. I want to go back to the United States and, you know, catch up with old friends.

I want to have some normalcy. So we did not go through the canal. We did not cross the ocean. We started to sail north again out of Panama into the Western Caribbean. And we spent another, I think, year, we didn't come back until 2019, but we spent another year traveling. but slowly making our way back to the United States.

And when we came back in 2019, we did it to honor our teenagers. So to answer your original question, they needed something that the constant travel wasn't providing. Initially, living on the boat provided this amazing contact with nature and other cultures and, you know, just the whole wild world. And it really expanded horizons.

But by the end, the horizons felt very narrow. You know, we had this very narrow way of living, and they really needed to come back to shore. They needed to reconnect with their cousins and their grandparents, and they needed friendships, and they needed driver's [00:27:00] licenses, and they needed their first cell phones, and girlfriends and boyfriends.

jujitsu and they needed jobs and they needed to try and figure out how to reintegrate and then how to follow their own dreams. And so we've been pretty stationary for the last four years. We've taken a few small trips, but nothing, you know, no big offshore trips for us because this is where we needed to be.

Jessica Fein: Your book is called “Leaving the Safe Harbor, the Risks and Rewards of Raising a Family on a Boat.” What was the biggest 


Tanya Hackney: It's hard to say what the biggest risk was. Obviously the risk to life and limb. It was not a safe life. We clearly left the safe life. So there was the physical risk of loss. There were obviously Tough questions that we had to answer in 2019 when we came back, we didn't know, did we homeschool them well enough that they could seamlessly integrate into the United States education system?

Did we provide enough social interaction so that they weren't completely [00:28:00] awkward or so different that they wouldn't be able to come back? Would they be angry at us for the rest of our lives because we took them away from normalcy and friendships and family? And it wasn't until we came back that we discovered that everything was going to be okay.

And so, I don't know, maybe I didn't even know what the biggest risk was when I set out. When I set out, it was always how to keep the toddler alive on the boat, how to keep everybody, you know, safe while we were on a long passage, really out in the middle of the ocean. You know, how to manage everything during a storm at sea, which is, you know, totally terrifying.

Those were the obvious risks, but the less obvious risks really came home to roost when we came back. That's when the rubber, rubber met the road and we discovered whether or not it had been worth it, really. It's one of the things you can't know at the beginning. And what'd you decide? Was it worth it?

Yes, it was worth it. And if you asked me if I would do it all again, the answer is yes. I might do some things differently, but travel is the best school. It's the best school [00:29:00] for all of us. We got a really, really good education. My daughter, she's now 19. She's probably heading off to the Coast Guard soon.

That's kind of the path that she's chosen. She speaks fluent Spanish, not because she studied it in school, but because we lived in Central America. My oldest two are now out of the house and they have kind of pursued their own dreams and that's been that's been really wonderful to watch them go and and start their own lives.

It's hard also to say goodbye to that phase of our lives. But I also know, okay, we didn't ruin their lives. It was a good choice for our family. 

Jessica Fein: So they're grown and flown. Are you and your husband going to go back to sea? What's your plan now? 

Tanya Hackney: We're still kind of tied to land. It's really hard to break free.

But we would like to do some longer trips. So I don't know what we'll do. We're now at a phase of life too, where we have aging parents. And so what I advise people when they ask me, like, would you do it again? Or how would you do it differently? I would say like, go, go when you're young, when you're healthy, if you can figure out how to, how to do it [00:30:00] financially, if you can plan for it financially, travel in your thirties and forties before you get old and sick before your kids need stability.

Before your parents need you because we're now in a phase of life where our family really needs us. 

Jessica Fein: I think it's really great advice to think about traveling when you're younger and it really does go against the kind of we all think we're going to work until we retire and then travel and it is a real turning of the script to think about doing it when you're young.

But as you say, figuring out how you can support yourself is such a key piece to it, right? How did you support yourselves and how do you advise other people to think about supporting themselves if they want to spend those high earning decades traveling. 

Tanya Hackney: You know, we've met so many people who did this and everybody did it differently.

We're unusual in that we didn't take a sabbatical. We did a complete lifestyle shift. And so we're the long timers. Not many people continue doing it, you know, year after year after year, even if it means saving up and doing a sabbatical. [00:31:00] I mean, we've, we've met lots of people on a one or two year sabbatical and we've never met anybody who regretted taking that time with their kids.

And even if it's only a year or two to travel, we've Some people set up real estate businesses where they buy homes and rent them out. And then they survive on rental income. My husband is a digital nomad. And so he took his brick and mortar consulting job and then just was able to move it online where he could, as long as we have a stable internet connection, you can make phone calls so he could stay in touch with clients and send emails back and forth and move data and things like that.

We've met other people who just choose to live more simply. So, you know, they'll work really hard for a while, save up a bunch of money, travel. And then when they run out of money, they'll come back, work, save up some money and then travel. It really, if you want something badly enough, you figure out how to do it.

And we just tell people not just about buying the boat, but if you have a dream, do whatever it takes to try and fulfill it. I mean, [00:32:00] do whatever it takes, because the good things are totally worth some of the hard things that you'll have to put up with in order to pursue it. If you want something really bad enough, you, you'll figure out how to get it.

Jessica Fein: When you came back after being at sea for 10 years, what had changed about you?

Tanya Hackney: So much, so much had changed. There's a turning point that I have written about. We were on a road trip in 2018, we had come back, we'd flown back to the United States from Guatemala to be there for my, uh, mother in law's 70th birthday.

We had promised her that we would be there for her birthday, and so we flew back to the United States, we took a little hiatus from the boat and traveled by car, and we took this road trip, and the transmission on our old Suburban that we had just kept in storage while we were traveling, Completely catastrophically failed on the roadside and this kind of thing would have just wrecked me, you know, my old self, uh, I would have been freaking out or crying and [00:33:00] I realized that day on the roadside, it's not that that was the day that I changed, it was the day that I realized how much I had changed where we're all standing there debriefing, trying to figure out what we're going to do, should we abandon the vehicle on the roadside and like buy a new car?

Should we buy a new transmission for this old car? What does this mean for the rest of our trip? I realized that I, I was calm and I wasn't upset. And I was like, Hmm, I guess that our plan wasn't the plan. I wonder what the plan is. And I approached that catastrophe with curiosity instead of with panic and fear and loss of control.

And so it changed me from the inside out. I'm a much less fearful person. I'm much less in control. Not that I had more control before, but the illusion of control was shattered when we moved on to the boat and I became comfortable with discomfort and uncertainty and much more go with the flow. I'm still pretty high strung and I still like to make a plan, but I also don't hold my [00:34:00] plans very tightly.

And I'm, I'm very spontaneous. So I changed personally, all of us learned so much living on the boat. There was a huge cultural shift too, that we made so many cross cultural friendships that we really view ourselves more as citizens of the world. It changed the way that we approach other human beings as well.

Not just, you know, how we approach ourselves and our, our circumstances, but also how we approach other people. It made us outwardly focused in a very different way. 

Jessica Fein: What's your biggest piece of advice somebody comes to you and says, Hey, this quote unquote American dream isn't working for me and I have another idea in mind.

It seems kind of crazy, but you did it. What would you tell me in terms of how I could do it? What do you say?

Tanya Hackney: I would say to collect verbs and not nouns. That you should look at your life, and if it's full of stuff that isn't making you happy, you can actually just get rid of that stuff. I would say start by downsizing.

You want to go on an [00:35:00] adventure, get yourself out of debt. Start getting rid of excess stuff. Surround yourself with other adventurers. And try and figure out what... pursuing your dream looks like. Take the baby steps in that direction. It might not end up where you thought that it would end up, but you should at least point your feet in that direction.

Jessica Fein: What verbs did you collect? 

Tanya Hackney: So instead of birthday presents and Christmas presents, we would have experiences instead. So we don't really do a lot of stuff based holidays, for example. So one year we went snorkeling on Christmas. We were in the Bahamas and I got up and made cinnamon rolls on the boat from scratch.

And then in the afternoon we went snorkeling. There've been countless birthday experiences. My favorite ones are going horseback riding with my daughter who loves horses for her 13th birthday in Bocas del Toro, Panama. Our 20th anniversary was spent surfing and then going up into the cloud forest in Costa Rica.

I have a [00:36:00] son whose favorite birthday memory is going four wheeling through the jungle on ATVs. They came back and it was like, The most dangerous thing that they had ever done. They were really like in the United States. It would not have been allowed. There would have been all sorts of legal reasons why they couldn't have done it, but they were off ATVing in the middle of the jungle.

Swimming with whale sharks is a huge memory for me. Climbing volcanoes is another amazing verb. So I have this lifetime of memories that we made. The stuff, I don't remember anything that I got for my birthday as a kid. But my kids, if you ask them, do you remember what we did for Aaron's 14th birthday?

And he'll be like, Oh yeah, that was the day that we jumped in the seven sisters in Grenada. We remember that. We don't remember the stuff that we get, but we remember the memories that we made. 

Jessica Fein: Last question. You were at sea for 10 years. You're back. You're on land now. Well, you're on a boat moored to land now.

Does life seem boring by comparison? 

Tanya Hackney: Sometimes it does. [00:37:00] Sometimes all of those things that we did feel like a movie that we watched, it was just like a whole different life and you come back and everything's kind of the same. And you're like, did we actually do those things? You know, did we sail to South America and back?

It doesn't feel like we've been tied to the stock for a couple of years. We like forgot how to use our boat. But then other times it doesn't, because we're the kind of people who just do crazy things. We are still the same people that bought a boat and went sailing with small children. And so if we have an idea of like, let's go do this thing, we just go do it.

And so there isn't any reason why we would be bored. Sitting still has taught me some really important things, like how nice it is to be part of a community. There's a group that meets here in the Keys on the beach on Thursday mornings, it's a prayer group. That has been amazing to be a part of a stable group.

The other thing about stability is that it allowed me to really write consistently, so I'm working on a second book. When we're traveling, it's hard to find the [00:38:00] consistency and the sitting still time to do the hard work of writing. So there've been some really good benefits. My kids have gotten to join sports teams and activities that they never could do.

I have a daughter that dances now and my son competes with jujitsu and my other daughter also does jujitsu. There've been some really lovely things that I didn't appreciate before about staying. So sometimes it seems boring, but sometimes, sometimes we need that. We need a little bit of both. We need adventure times and then we need staying still times.

Jessica Fein: Well, thank you so much for sharing it. It gives us a glimpse of what that adventure life could be like, but also maybe a little bit of inspiration of, you know, maybe it's not the craziest idea and maybe by taking those baby steps, even if it's not going to see for 10 years, even if it's, you know, the weekend trip, maybe it's something that I could work up to and that I could do.

So it's really just a remarkable story. Thank you so much for your time today. 

Tanya Hackney: You're so welcome. And thank you for letting me share this part of my story. 

Jessica Fein: Here are my takeaways from the conversation with Tanya. Number [00:39:00] one, travel or do the adventure now. Most of the time we can figure out a way if it's something we want badly enough.

Number two, Baby step your way into your dream. 

Number three, try coaching yourself by asking what you have to do today. Can you make the call or write the email? Break it down into the tiny things that feel manageable. 

Number four, when your goal seems audacious, whether it's moving onto a boat or ziplining, ask yourself if you'll regret not giving it a try.

Number five, it's possible to take time for yourself and find alone time. Even if you live at sea, on a boat, with six other people. 

Number six, my favorite, collect verbs instead of nouns. 

And number seven, there's a time for adventure, and there's a time for staying still. 

I hope you enjoyed this episode. If you think a friend of yours might like it, Please forward it on to them and I'd so appreciate taking a second to rate and review the show.

Thanks so much. Have a great day. Talk to you next time.