Ep. 387 The FIRE movement and building a life by design with Jake Wysocki

What would it look like to design your life the way you’d design a great product – starting with the why, testing before you commit, and building towards a shared vision with the people you love? Design thinking strategist Jake Wysocki shares how intentional decision-making, the FIRE movement, and honest conversations with your partner can help you stop living by default and start living by design.

Key moments

Key resources

• Jake Wysocki – Intentioncraft: workshopwhy.com
• Jake’s State of the Union approach – as shared on the Mindful Fire Podcast
• The Simple Path to Wealth by J.L. Collins
• Die With Zero by Bill Perkins
• Good to Great by Jim Collins
• Great by Choice by Jim Collins
• The 7 Habits of Highly Effective People by Stephen Covey
• Ramit Sethi’s podcast (money conversations for couples)
• Dr. Becky Kennedy – Good Inside podcast and book
• The Anxious Generation by Jonathan Haidt
• Book a call: onestepoutside.com/call

Fire movement

Anna Lundberg: Okay, hello everyone and welcome back to this month’s interview. I’m here with Jake Wysocki and he is in Wisconsin in America. So I will put you straight on the spot, Jake, and ask you the million-dollar question, which is what does success mean to you?

Jake Wysocki: All right, so I got lots of thoughts on success, but maybe I’ll start with what it used to mean to me only a few years ago, before I left corporate. And that was basically just like, get the work done, put it out there, just do what you promised. Nothing can change, just get the work done.

But now for me, success can mean a lot of different things. So I’ve quit my job and now I’m an entrepreneur. And that means for my business that I’m profitable and I’m serving my customers to the best of my ability. But the other thing with success is really just living the way that I want to live. There’s a whole FIRE community backstory that we can get into later as well. But that’s been part of my journey – how do I actually live the life that I want to live, and that my wife and I want to live with our family.

Anna Lundberg: And I definitely want to come back to that piece. But starting with you, what has been your process of rewriting those scripts of just get the job done to identifying as an entrepreneur? And I love that you emphasise that, yes, we need to be profitable and actually be selling, because otherwise it’s not a successful business, right? But also these other things. And what’s been that journey for you?

Jake Wysocki: Yeah, so a few things that come to mind. So my company’s name is Intentioncraft. And that kind of hits at the core of my philosophy, which is think about what you’re trying to do and why so that you have the best chance of succeeding. And a lot of times, though, why are we doing this seems obvious to people, unless you stop and actually think about it and you realise the actual why of something is often different than we assume.

So let me try to give an example. Why do we work? It’s like, well, because everybody works. That’s just what people do. But if you pause and think, you can find lots of examples from the FIRE community, for example – which is financial independence, retire early.

For anyone listening who’s not familiar with it: it’s basically the concept of saving enough that you can live without having to work. And it gives you freedom. It’s not so much about the retire early. It’s more about the freedom that it gives you.

For me, it’s all about taking a step back and actually thinking about what am I doing this for? And a lot of people just think, well, I need more. I need to buy that house. I need to go on those vacations. But if you stop and think, why do I want those things? They might still be important to you. But then you might realise, well, we need a house for these reasons, so we don’t need that particular house we were looking at. We can scale down and that gives us more freedom. The point is, take a step back – consider those big decisions, really get clear on those, and it makes everything else easier in life.

Anna Lundberg: I love that. And as you know, I think we connected because of the intentionality crossover. It’s such an important piece for me too. So much of how we live – because we’re so busy and life is just lifing around us all the time – it’s just head down, autopilot. At school, it’s get the grades, go to another school, get the job and the promotion. It’s the ladder. And then in our personal lives as well, it’s meet that person, have the children, and then the house. It’s really just, why are we doing it?

So again, in your story, what was it? Was there a trigger or was it just a gradual awakening that happened?

Jake Wysocki: That’s a really good question. I don’t think anyone’s ever asked me that before. So let me just think for a second.

I think it started in college. One of my first jobs was working with children in Gainesville, Florida, where I was a counsellor and a bus driver and all these other things. And at one point I became a supervisor. Part of that supervisor training – the owners were really big on Jim Collins’ first book, Good to Great, and the hedgehog concept. And part of the training was introspection, the Seven Habits of Highly Effective People, which I actually just reread recently and it still holds up.

The owner had given us goal packets to complete – what’s your ideal day look like, imagine 20 years from now, things like that. And I really enjoyed that. And I think that was the seed.

And then one of the big decisions where I really leveraged this thinking was right after my wife and I got married in 2015 – we quit our jobs and we travelled for a year. I remember thinking, am I really going to do this? Am I really going to go off that paved path – get a job, climb the corporate ladder, and then sail off into the sunset when you’re 70?

Which, if that’s what you want to do, I’m not knocking it, but I also think you should do it intentionally. So my wife and I stepped back and said, what do we want to do? We hadn’t really travelled much. We were living in San Francisco at the time, which is really expensive. We were saving up theoretically to buy a house. And we kind of projected a little bit – looked at the financials and looked at what we want our life to look like. And then we looked at, well, what if we just travelled instead?

We almost chickened out, honestly. I told my work that I intended to leave, and they offered me six weeks’ vacation. We almost took it. But the question we asked ourselves was, would we regret not doing this the way that we’d originally envisioned? And we decided, yes, we would. So we went for it. And that thinking has carried through for us since.

Anna Lundberg: You know, it mirrors my story, although individually for me. And you remind me that I did a Seven Habits training – it was like a three-day training. And I think my grandmother died around the same time. We went around the room saying, why are you here? And we’re all talking about finding the meaning of life and living in the moment. And then this one guy was like, I just want to be a better leader. Which is fair enough. And all of us were like, oh, we’re going to find ourselves. So I guess you have to be receptive to it. That’s the lens you bring.

I also travelled – I took a sabbatical initially, but halfway through I left because I felt if I came back to my very comfortable life, nothing would have changed. And what I’ve realised is it’s not about leaving the job. Most importantly, you carry those scripts with you.

So has that been something in terms of the more mental process – have you found when working for yourself, is it easy to get caught up in those old corporate scripts, even though on paper you’re doing this for freedom?

Jake Wysocki: Yeah, so it definitely is. And I’ll give you a few examples. The first thing I want to mention, though, is you were talking about should. One of my favourites around this topic is don’t should all over yourself. I love little phrases that stick, because they really draw attention to the problem. Another one I love when I’m conducting research or doing a workshop is put your brain on speakerphone. That usually gets people.

So for scripts around work – let me share a little bit about what’s going on in my household right now. My wife is supporting us day to day. Because of FIRE, we don’t really need to worry too much about the future. We have quite a bit saved up as a nest egg, and it should grow to be very good for us in the future. So we really just need to worry about the now. And my wife’s work can support us for now. That’s what enables me to do what I do without stressing, which has really helped prevent a lot of what I’ll call the fight-or-flight mentality of corporate – I need to do it or I’m going to get fired.

But the fundamental challenge we’re having right now is she is, we’ll say, sceptical about how much she likes her job. There have been some changes recently, and we’ve been having a lot of discussion about, OK, well, how long do you stick this out? Do we really need you to work? And so we’re at this point where it is time to examine those scripts. And the way we’re doing that is by mixing intuition and logic. Intuitively, it feels like – if you’re really unhappy, we should find a way to get you out now. But also, what does that actually mean for our life? So we’re looking at it from both perspectives. And that’s how we sometimes examine our scripts: when we notice something’s wrong, we stop and we actually analyse and think about it and discuss it.

Anna Lundberg: And it’s such an important realisation for people who may be early in the journey – it’s not just that one decision, right? Things change. An assumption is, OK, one partner has the well-paid job and the other is more free to imagine and dream and maybe build something for the future. But hang on – that person is no longer enjoying the job, or the manager has left, or they’re made redundant. Suddenly that shakes the ground and you have to rethink again.

And it seems so obvious that you should do it with your partner, because of course you’re never making these decisions in isolation. You have a house, you have children. I made my decision very much in isolation – I had a cheap flat I could give up right away, no real obligations. So I was hugely privileged to be able to take all that risk. There are so many things that make my situation different to someone who’s listening with three kids in private school and a big house. But all the more powerful to rethink those scripts, I suppose.

Any tips from doing this together as a partnership?

Jake Wysocki: Yeah, I got a bunch of thoughts on this. I’ll shout out Ramit Sethi – he’s big in personal finance, and if you’re married and you have money conversations, his podcast is amazing. My wife and I get along really well and we’re really dialled in on our money, but we still love listening to the show.

The answer to your question is: I think shared goals and having a shared vision. For my wife and I, we are playing together on the same team. A common thing I hear is, well, I’m making money and I want to spend it the way I want to spend it. And my spouse shouldn’t spend as much because they don’t make as much. And I just don’t understand that view of the world. We got married. We are now a team. So a dollar I make is your money and the dollar you make is my money. And our goal is to figure out what do we want to do with it and what do we want our life to look like together.

There’s no resentment in our marriage, as far as I’m aware, because we are working together towards a goal. And our goal is to do another trip like we did, except longer and without our kids, in the next four to five years. We’d actually just started making it a little more concrete than fuzzy this last month. And so that goal gives us a timeline, gives us more concrete things to look forward to. Then we can start saying, should we buy that thing? Or would we rather accelerate our plans? Having a concrete thing we’re moving towards makes everything clearer about what the trade-offs are in the day-to-day.

Anna Lundberg: And how do you actually do that? Is it a New Year’s kind of sit-down with a big piece of paper? Is it organic throughout the year?

Jake Wysocki: So my wife and I do what we call state of the unions. I have a design thinking background – which is basically structured exercises mixed with a human-centred mindset. I’ve used those skills to design experiences for my wife and I to basically do our own workshop. I call it the quadrant two space, from the Seven Habits – important but not urgent. It’s so hard to find time for that, so we actually schedule three times a year, about half a day, to do this workshop between us.

It starts with what I call the pillars exercise, which is more commonly known as the wheel of life – looking at your life across about eight categories: relationships, health, work, and so on. We always start with a check-in: where are we at now? We do this separately first. We rate each category on an A to F scale – like a report card. And then we come together and share and discuss. That gives a sense of what’s important to us and what might need focus because it’s going the wrong way or not getting enough attention.

Anna Lundberg: Are you doing that together, sort of a score each, or as a combined team score?

Jake Wysocki: We do it individually first. We are a team, but we’re also individuals first. And then we figure out how we’re working as a team and where we can support each other. So for example, if my wife were to rate work right now, it would be a pretty low score. And mine would be pretty high because I have the ability to control my own destiny to a certain degree. And she does not.

This year, it was: we’ve been talking about doing this big trip. Let’s start making it real. And so we talked about what the purpose is. Why do we even want to take a trip like this? We landed on: besides being fun, we want our girls to be able to feel confident walking into any room they enter. That was what we ended up landing on, which is kind of counterintuitive. And it’s debatable – which is actually the sign of a good purpose, if someone can disagree with it. So now that gives us focus on how to actually design that experience to accomplish what we want for our girls.

Anna Lundberg: Did you say that’s an annual process or are you checking in throughout the year?

Jake Wysocki: The check-in is three times a year. We were trying to do it every quarter, but life gets a little busy. So we decided – instead of trying for four and landing on three, let’s just commit to three and land on three.

Anna Lundberg: And do you imagine involving the children in the process at some point?

Jake Wysocki: Yes, 100%. We haven’t yet. My eight-year-old certainly could. And especially for the trips that are coming on the horizon, we’ll definitely start including them more and more. I want to do something like a family mission statement – we’re the kind of family who… – some exercise like that in the next year, with at least my eight-year-old and probably my five-year-old.

Anna Lundberg: Yeah, it’s very empowering for them to feel involved, even if they’re not making the big financial decisions. It gives them responsibility from an early age.

Jake Wysocki: Exactly. It’s like, well, do you really want to go to Disneyland? Let’s talk about what that means. I want to start peppering in how this works. I’m a big Dr. Becky fan – she basically advocates for treating children like actual humans. They’re more sophisticated than you think, and you can have more real conversations with them than many people assume. We’re definitely raising our children to be more involved, to hear what they think, to bring them on the journey. If you’re asking me something, you’re old enough to hear at least some kind of reasonable answer.

Anna Lundberg: I’m with you. I think my partner says I tend to be too sophisticated with my answers, but I figure I’d rather be honest and talk about it and eventually they’ll understand, rather than trying to oversimplify things.

In terms of the business model – and because you talked about FIRE – what does that mean concretely in terms of your financial and business decisions?

Jake Wysocki: So my favourite resource, which I’m actually rereading right now, is called The Simple Path to Wealth by J.L. Collins. That lays out the primary thesis of FIRE. The concept is usually rooted in simple index funds in the stock market that should likely grow at a certain rate. You’re building an asset that will spin off money or grow that you can pull from such that it won’t go down over time, but you’ll have enough to live off of. The 4% rule is the typical thing people in the FIRE community reference – whatever your amount of assets are, you can take out 4% pretty safely without it drawing down to zero.

What I love about this is instead of the concept most people have in their minds – I just need more, I need $10 million, I’ve got to keep working – there is an actual number that you can calculate that is a reasonable stopping point for wealth accumulation. And then you can make decisions from there.

And what I love about this journey is every step along the way, you gain more freedom. It’s not that you have to wait until you hit a certain number. I’m in what’s called coast FIRE – I don’t need to worry too much about saving for the future, I just need to pay for now. That’s more freedom than I had years ago.

I’ll also shout out another book that’s a great companion to the whole FIRE conversation – Die With Zero. Have you heard of this book?

Anna Lundberg: No, I like the idea of it.

Jake Wysocki: Die With Zero is an amazing book. The high level is: if you reach the end of your life and you have enormous amounts of money, you have in many ways wasted your life energy. The thesis is there are certain points in your life where things are harder, if not impossible, at different stages. The example he uses is skiing – if you’re 60 or 70, do you think you’re going to be hitting the slopes the way you might want to when you’re younger? He encourages you to think about where you are in your life and what has the most value now.

The phrase he uses that I love, and that I’ve actually worked into the pillars exercise, is memory dividends. We think about money dividends – he talks about memory dividends. If you make a memory on a trip, you see it periodically on your screen – that is harvesting more of the benefits of taking that trip. It’s not just the trip itself, it’s the memories you have and the stories you tell and how it impacts your life. And the sooner you can have those, the longer you have to reap the rewards.

And just to bring it back to kids – my oldest is eight years old. She’s basically halfway out of the house from a practical perspective. Even if she stays longer, she’s going to have her own life at an ever-increasing rate where she’s going to want to hang out with her friends and not her dad. And that puts it into really stark contrast. Time is limited and time changes. I don’t have forever to do things. So when do I want to do it? Let’s be intentional.

Anna Lundberg: I love it. And on one hand, there’s the big meaning-of-life platitudes – life is short, yes, we know. But on the other hand, I really like the Ramit Sethi money conversation. What is the number? There’s a sense of enoughness. And that’s really the heart of the work I do too – bringing the beautiful life-is-short vision into the real world by going, OK, right now I’m a three out of ten in terms of money satisfaction. What do I need to do? What are the levers we can pull? What are the dials that we can turn? That’s so much more empowering than just keeping going and hoping for the best.

Jake Wysocki: 100%. Can I add something to that? I love planning, but I don’t love rigid planning. Let’s take a quintessential trip. A lot of people say, well, I want to be spontaneous. And I say, great – plan time where you can be spontaneous, and then plan the things where you can’t be spontaneous because you need to book ahead of time.

What I love about this – I think of it like going out to eat with friends. You say let’s go out. And it’s like, how about Mexican food? I had Mexican last week. How about Indian? I’m not really feeling Indian. My point is you’re giving them something concrete to make decisions against. And that’s what plans are for me. You’re putting your stake in the ground, not because you’re cementing it in forever, but because you’re making a concrete plan you can base different decisions off of. Having a decision you’ve made doesn’t mean it needs to stick forever – you can always remake it. But having one turns it into a tool to make even better decisions as you get closer.

Anna Lundberg: There’s a couple of concepts that come to mind. One is the idea that creativity comes from constraints. If you can do anything you want, anywhere, with anyone – suddenly you can’t do anything, and that’s the paradox of choice. Giving yourself some parameters – OK, it’s going to be this month, or it’s going to be a hot trip or an adventure trip – suddenly you can filter and make far more concrete decisions. Rather than business as usual carrying on and the whole year is gone.

Jake, I feel like we could talk about so many different things. I’m conscious I haven’t really asked you what it is you do. Did you want to share with the listeners what is the current iteration of your business?

Jake Wysocki: Thanks for asking. So I’ll just tell a brief story and then I’ll get into what I do.

I mentioned my one-liner used to be helping millennial parents live regret-free. That’s what I wanted to do when I first quit corporate. I started down that path and had some early success. And along the way, somebody knew my background – in corporate I was a design thinking strategist, teaching people in my Fortune 200 company how to run workshops and move a project forward using these principles.

And somebody reached out and said, Jake, I’m freaking out. I’ve decided to do an in-person coaching event and I just committed to it, but I don’t know what I’m doing. Can you help me? And so that brought me back to my corporate roots. And I said, I really like doing this. I really miss this. And I think I’m going to pivot to doing that. That was about a year and a half ago.

So now what I do is I build five-star workshops for established experts. Usually somebody who has a lot of expertise and wants to do a group coaching programme or a workshop or some structured transformation – I help them get clarity first, and then I build most of the things alongside their knowledge, shaping it into a world-class experience for their clients that they love delivering and are proud of.

Anna Lundberg: I love that. And it’s quite reflective of a journey I see again and again. We all come out of corporate and go, I’m going to live a regret-free and fulfilled life. And a lot of coaches come out and say, I’m going to coach other people. And it’s all very fluffy, nice language. Also because we’re kind of rebelling against the corporate world, so we draw a line through the very skills that make us so commercially strong. Then there’s a process we go through organically – and it’s hard to skip that phase – where someone goes, hang on a second, you can do these amazing things I can’t do at all. And then we land on a far more commercially viable proposition.

So it’s reassuring for people to hear that it’s a very common journey. You can land on something drawing more on your background while also bringing in new insights and things you’ve learned along the way.

Jake Wysocki: Yes, 100%. And I’ll share another thing from Jim Collins – a different book called Great by Choice. He talks about bullets before cannonballs. If anyone’s an entrepreneur who hasn’t read some of Jim Collins’ stuff, it’s really good.

Imagine you’re on an old-timey ship, like Pirates of the Caribbean. You only have enough gunpowder to shoot about one and a half cannonballs. Are you going to chance it and hope you hit that ship? Instead, fire a few bullets first until you know you’re aimed properly – and that’s a really apt metaphor for how I approach my business. I didn’t take out a huge business loan. I’m trying things out. I’m experimenting. It’s low risk, it gives you a lot of information, and then allows you to make a better decision. It’s tied in with a bias towards action.

So my advice to anybody listening: if you’re curious about something – how can you go test this idea? My friend who reached out basically asked me to fire a bullet. I did it for free, and I realised I really missed this. No risk, I wasn’t committing to anything. I just helped her out. And I realised maybe I should go all in. I did a few more bullets. And then I said, I’m pivoting. You don’t have to be all in from the start. Find a way to dip your toe in.

Anna Lundberg: Yeah, I love that. I’ve been doing free workshops locally in person and it feels like, oh God, I can’t believe I do it for free and I don’t have time for that. But actually slowing down to speed up – you’re giving value, but also in the meantime you’re refining your messaging, meeting connections. You don’t know that someone’s going to say, wow, this is exactly what we need. And the bullets and cannonballs feels like a more sophisticated evolution of ready, fire, aim. But coming from those scripts of being a good girl at school, getting the top grades – I’m going to launch this programme, I’m going to make it perfect, I’ll spend months crafting it with AI, and then nobody wants it. Rather than a survey here, a free workshop there, a low-paid thing there – and see what sticks.

Jake, one more and then we’ll wrap up.

Jake Wysocki: OK, thank you. So this is huge in many of the clients I work with. What I tell them is: let’s figure out the foundation of your workshop or group programme before you actually build it. You’re going to understand what you think you’re trying to do for your clients – your promise figured out, why they’d care about it. Then you go sell your programme first, or get people to sign up for your workshop, before you design any slides. You have a really rough idea – I call that the 10% – and before you actually build anything, make sure somebody wants it. So many people spend months building something and then nobody wants it. You can build a great programme that’s still rough around the edges initially and deliver real results.

Anna Lundberg: It’s the MVP, isn’t it? It doesn’t have to have the fancy perfectly-designed cards and software and automations. What’s the result they want? How can we get them there? They’ll rave about it. Then we can get fancy later.

Jake Wysocki: Yes, exactly. And this will be my last comment. I’ve been doing some work on what my big premise is. And it’s: instead of perfectionism, think about excellence. The difference is that perfectionism assumes there’s a point where it’s done, it’s perfect, and you don’t need to change anything. But excellence – that’s the pursuit of continuing to make it better because you care. You can start somewhere and continue making it better, versus thinking you need to reach some certain point that you’ll never reach anyway. Don’t think about perfectionism. Think about excellence.

Anna Lundberg: I think it’s such a form of procrastination. OK, I’m going to make this book perfect. Oh, it’s not perfect. So I’ll start on another book. It’s just chasing your tail. What I love about excellence is it gives us permission to still have very high standards and to keep evolving and improving, but your 80% might be someone else’s 100%. And especially if you’re not releasing it to the world because you’re waiting for perfection, you’re not helping anybody. So many lessons for those rewriting those success scripts.

Jake, where can we find you and what’s the next step if someone’s curious about the way you can help them?

Jake Wysocki: The easiest place to go is workshopwhy.com. That’s where you can get my free resources, including how you figure out what your workshop or group programme should be about. And you can get in touch with me over there too.

Anna Lundberg: Amazing. What a great URL. Thank you so much, Jake. Really enjoyed the conversation. Some really interesting aspects there. We’ll make sure we gather all the resources, next steps and links for everybody. Thanks so much for sharing so generously of your time and insights.

Jake Wysocki: Thanks for having me. This was great.

Anna Lundberg: If this conversation resonated with you, I’d love it if you could share it with someone who’s in that in-between place right now, questioning the scripts they’ve been running but not quite sure what comes next. And if you’re building your own thing and want to do it with more intention, more structure, and a little less chaos, hit subscribe so you don’t miss what’s coming in the next few weeks.