Is financial freedom worth waiting for?
5 unconventional ideas from 'The Other Side of Enough' series
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The Way of Work explores stories of where we fit in the world of work. This series, The Other Side of Enough, explores what life is like when you have enough to never work again. I just completed the last interview and am now reflecting on the key lessons from the series.
We are all chasing “enough.” We want enough money. Enough things. Enough time. Enough love. We crave the feeling of having enough, of being enough.
Many of us think that when we have enough, we’ll be free to do what we want. But what does that freedom actually look like?
So I decided to hear from people who have enough. In the world of work, they’ve reached the finish line — or at least what many of us think is the finish line.
In the series, I spoke with a kaleidoscope of people to get a better picture of what it’s like to live inside the dream of financial independence. Less about how they achieved this milestone, and more about what happened after. I wanted to explore bigger questions, like:
Is “enough” worth working toward?
Is “enough” worth waiting for?
What do people do when they don’t have to work?
And what does it mean for the rest of us?
These aren’t just abstract questions. Because if you are killing yourself to get to the other side of enough, it might be useful to know what you’re fighting for.
As I spoke to each guest, their stories revealed recurring themes – unconventional lessons about crafting a meaningful life. Here are some of the best ideas from the series…
I. Live the perfect day, forever
When we picture someone with financial independence, we often envision an endless vacation. A highlight-reel-life filled with extravagant adventures and magical moments.
But the reality, as I’ve learned, looks very different. Most of the people I talked to don’t live exciting lives. In fact, their lives sound quite ordinary.
Many of them have curated a wonderfully boring day, but boring in the best way possible.
, for instance, is one of the most intentional architects of his time that I’ve encountered. He shared a simple exercise that have helped shape his days:“Imagine your perfect day. You wake up. Where do you wake up? Who do you wake up next to? What are the settings? What do you feel? What do you do first?”
For him, that includes a slow morning, some writing, work on his indie project, physical activities (e.g. surfing, jiu-jitsu, running), and one meal a day with a friend. That’s it. Simple. Not a ridiculous fantasy, but something he’s crafted with care.
What’s notable is that Naz created this picture before he was independent, then worked backwards and made the necessary sacrifices to move toward his perfect day over time. Independence was just the latest unlock in his progression (he’s not done yet, by the way).
Naz wasn’t alone in this approach. Omar traded a “pretty horrible day-to-day” as a founder, for a simpler life of independence. As he described:
“[I’m working on] just finding joy in my day-to-day life and gravitating towards that. The more I focus on finding joy, the less depressed I get.”
What if, instead of pursuing an abstract goal of total independence, we designed our perfect day, then reverse engineered how to get there? Not waiting for some monumental event to flip the switch from drudgery to dreams. How close is your current life to your version of a perfect day? And what small steps could you take to move closer, without waiting for “enough”? Naz again:
“Can you actually live your perfect day forever? Everyone could shoot for their ideal day, in their ideal location, and then work backwards, from that goal.”
II. Prioritize where you “play offense”
Most of us are playing offense at work. We bring our best energy, best focus, and best self to our jobs. We even train for it – books, podcasts, and even meditating as a means to an end of better work performance.
And the rest of our life? We’re playing defense. If we’re lucky, we do just enough with our relationships, get just enough sleep, have just enough exercise, and so on. And sometimes, we’re not even doing that.
We’re just getting by, getting through life, on the way to getting back to work.
Avon describes his shift in thinking, from playing offense at work to offense at home, especially with his kids:
“I don't think I'm necessarily spending that much more time with them than I was before. [But] there's a kind of a qualitative difference in the way I'm engaged with them.
I feel like I'm basically their coach or mentor, or something like that. There are ways in which I'm really engaged now in their lives, that really bring me joy.”
Maybe you’re in a season of life where work demands your focus. There’s nothing wrong with that. But what about when you meet your future spouse? Or when you have kids and they still enjoy being around you? Or when you’ve hit midlife and realize your professional success has consumed every ounce of your identity, leaving little else behind?
You don’t need to retire to shift your priorities. Sometimes it’s as small as working from home an extra day, leaving the office a little earlier, or choosing to invest your best energy into the people and projects where you find the most fulfillment. As Esther Pearl puts it:
“Don't give the best of you to strangers and bring the leftovers home.”
Where are you playing offense?
III. Don’t ask too much from your purpose
If you grew up in America, you were probably taught that purpose = huge ambition. The good life, it seems, is a utilitarian calculation of the number of lives impacted X the impact per person. I mean, if you aren’t changing the world, then are you even here?
“Not so long ago, we never even considered our work would scale. But now, it’s the expectation.” - from Scale down, after scaling up
This frame can make anything less than an insatiable ambition feel disappointing. We see other people with impossible focus and grand devotion, and are left with a type of FOMO where nothing has “called” us to the same degree.
What may be happening, instead, is that we’re really chasing extrinsic motivation, while failing in our ability to recognize the intrinsic motivation within ourselves.
No one articulates this as well as
when he compares big “P” Purpose and little “p” purpose:“Big ‘P’ Purpose is the kind that makes us feel stressed and anxious. It is usually very goal oriented. It's usually very big and audacious.
[But if your purpose is] goal-based and it's one of these big goals, most likely you're going to end up disappointed. This is a very scarcity-oriented version of purpose. It's win or lose. All or nothing.
Contrast that to little ‘p’ purpose which doesn't worry about goals as much, but it's much more interested in process. This is very abundance-oriented.
How many things can you do that you enjoy doing? Well, they're countless.
And once you stop worrying about the goals and just enjoy doing what you're doing, it becomes so much easier. It's not winner-takes-all. Everyone can do this. There's no such thing as failure.”
Maybe you've been hoping "your thing" would be much bigger. More impressive. More all-consuming. Or, at least, something cooler to tell other people.
Maybe you think it will whack you in the side of the head as obvious. But maybe, instead, it'll come to you in much more subtle ways, and you have to be patient and listen carefully. Maybe it won’t be “your everything,” but found in smaller, overlooked moments every day.
IV. Follow your “energy”
Chasing money or success gives us a certain kind of clarity. It’s the easy way out – we won’t have to wrestle with the bigger, messier existential questions.
For those who’ve made money or achieved success, it can feel oddly destabilizing. Without that fire-in-the-belly driving us forward, we might even find ourselves wishing we could go back to the hunger we worked so hard to escape. It’s a strange paradox: we resent our contentment.
This flip is perfectly captured in the 6-minute film MORE , by Mark Osborne (nominated for an Academy Award):
Jeff, a founder who exited his company, described how the simplicity of the chase gave his life direction:
“There's a benefit I didn't realize while working and chasing money. The outcome was just so simple.
Bang! Bang the rocks together, monkey! Bang the rocks, and then get more rocks. Bang them together. Just keep doing the same thing.
[But people don’t think about] when the monkey [doesn’t] have to bang rocks together anymore. There's a sense of loss about it.”
Jeff now has an alternative aim: he chases energy. Simply: when he does something, is he energized by it? Or drained?
“Negative energy is putting your time and resources into something that sucks and you don't want to be doing.
There's an extrinsic-should and intrinsic-should. And when I retired I certainly acted on the extrinsic-shoulds.
‘You should do nonprofit work. You should sit on boards. You should mentor startups. You should be an angel investor. You should, you should, you should.’
And I didn't like most of them.”
Positive energy, however, reinforces itself. When you do it, you want to keep doing it. He says to pay attention to…
“...inklings where you're drawn to something. You've had one of these ideas that keeps calling you. Just take that 1st step toward the energy.”
“Energy” can be a far better guide than the more nebulous concept of “intrinsic motivation.” We can notice and pay attention to what brings us energy, while ignoring the external voices telling us what we should do.
V. Expose your dreams to air
I’m guessing that you have a dream to do something amazing in the future, but ONLY IF something else happens first. We always have a list of requirements, some level of “enough,” before we get to follow our dreams.
But as Brandon (aka the Mad Fientist) found, it isn’t so easy to flip that switch. He realized something important: dreams are safer as dreams. We’ll keep them locked away in our heads, away from the cruel whip of reality, as he did with his dream of making and playing music:
“I don't wanna try and fail, because then my dream is dead. So instead, I just won't do anything.”
Brandon delayed his dreams for years, before and even after independence. It wasn’t until he confronted his self-doubt that he realized the cost of waiting:
“I put everything off until retirement, which was stupid. I think I would have done it a lot differently.
I could have easily… been pursuing all my big goals even with the job.”
He also pointed out how exposing your dreams to reality can reveal whether they’re truly worth chasing.
“If you think you want to travel the world as a nomad, then take a sabbatical, do it for 3 months, and realize that's too much and you don't like it.”
Waiting for the perfect time to start – or worse, waiting for a dream that may never happen – seems too big of a risk. What if the right time never comes? Or what if you discover too late that your dream was never worth pursuing in the first place?
Instead, what if we expose our dreams to air, earlier? Even if we can’t fully realize them, we can test them in bits. So that we may realize whether it’s a dream that requires waiting. Or the moment of “enough” we’ve been waiting for, is already right here.
In the end, what may be hidden beneath all these stories is that we never really reach a point of “enough.” We may graduate from one enough (e.g. money), but around the corner, there another new search coming for us. It’s one thing to see financial freedom as a worthy goal, but another to see it as The Endgame — the perfect destination where we automatically get to live happily ever after.
Instead, I think “enough” is a fictional place — it’s made up inside our heads. But still critically important, because it challenges us to rethink what we value, how we spend our time, and what we’re really want out of life. And we decide when we arrive.
Next up, in The Other Side of Enough, we’ll give some advice for people who are still on their path to enough.
I love this series so much! I had the secret dream of becoming a full-time youtuber for a while until I took a 6-month sabbatical and tried it out. I realized it doesn't fulfill me enough to be my main thing. I still love it as a side thing and now I feel a lot more satisfied with how much time I have to put towards it. Before that, I was always frustrated with not having more time for making videos.
Now, I wonder if sometimes we even know deep down that our dreams aren't what we really want but we don't have a better idea yet, so we are scared to challenge it by trying it out, at which point we would be forced to face the fact that we have no idea what to do with our lives. I think that might have been true for me. But since I have tried that and realized that destroying your dreams is not that bad (it was actually exciting to think up and try out some new ideas), I have less fears around just trying things out on a small scale or on the side or for a limited time - and at least it gets me closer to finding my path every time.
Excellent post. I think you hit all the major pieces. I am at the end of a two year sabbatical after selling a company, and at the precipice of jumping back in. This really crystallizes many of the issues foremost in my mind such as the “perfect day” that I’ve built up over two years off, and the focus on process required (boundaries and means) that would entice me to return to the world of startup building in a saner way.