There are lots of people who write beautifully about lifestyle design. But for all the insights these writers share, almost all of them begin sharing their wisdom on how to live a happy and fulfilling life only after they’ve become quite wealthy.

“I made millions and it didn’t make me any happier,” is a common theme, followed closely thereafter by a nudge to work less, live in the present more, and optimize your life for freedom over earning potential.

Well no shit.

I think most smart people—even those that aren’t yet wealthy—recognize this to be true even if they haven’t realized it themselves. Our happiness is tied to much more than our bank accounts.

But I think for those of us that aren’t rich, these well intentioned messages often provoke a natural and common reaction…

“Yea, that’s easy for you to say.”

If there were millions in my bank account I’d be working less and living in the present an awful lot more, too.

It’s not that this advice is in any way wrong—in fact, I think it’s quite important that this perspective is shared by people who have had the experience of making boatloads of money. It’s a proof point that money doesn’t by happiness, and it’s useful for that reason.

But these words often land for the rest of us as at least a bit inauthentic—especially when the writer did anything but what they are suggesting on the path to building wealth, only to turn around and tell us not to do what they did. It’s not that this advice is hypocritical per se, but nobody wants to hear a rich person tell them not to do the things that they did to become rich. And it strikes me that the alternative is most often the polar extreme—a monk sitting on a hilltop who has rejected most societal structures altogether as he tells us wealth and happiness come only from within.

There seems to be no middle ground—who is writing for those of us that aren’t ready for the hilltop, who want to participate in the “normal” world? And who is writing about how to build wealth and happiness, that’s not already rich?

There’s a void here—one that I’d like to try to fill.

I’m not rich

Let’s start by getting this out of the way—I am not financially wealthy. Sure, if you look at the landscape of all the human beings on the planet, I’m doing quite well. But by the measure of income in developed countries—and by the measure of just about anyone reading this—I am definitely not rich. I had a few jobs in my 20’s where I was paid well, but my income has been very modest throughout my 30’s as I’ve been working on my start-up, Outseta. Chances are, you’re making more money than me.

And for the record—I would love to be rich!

I like money a lot and I’m quite skilled at spending it. I seek it far more for the freedom it provides than out of a need for fancy things, but make no mistake about it—I’d like to do very well.

I’ve had a few opportunities so far in my career to make a lot of money, but in every instance except for one I’ve turned those opportunities down. I’ve had the opportunity to work in senior positions at big tech companies. I’ve had the opportunity go to into venture capital. But I never jumped on those opportunities—those decisions have always come down to me prioritizing my own personal freedom over opportunities that would require a lot of time, albeit for a lot of money. I am for the most part very happy with those decisions, although I do increasingly have a sense of “OK, it’s gotta be time to get mine at some point.”

I’m working on it.

If you look at wealth by almost any other measure, I am decidedly wealthy. I’m healthy, I have a beautiful family, I’ve had all kinds of wonderful life experiences, and I have as much fun as just about anyone I know. My wife will tell you I bitch and moan about things like anybody else, but I’ve always been quite happy. The world, generally, amazes me.

Everyone’s journey toward building wealth and happiness is ever evolving, and always quite personal. There is no blueprint, but this is a topic I’ve thought about and acted on starting at an earlier age than most people I know. My hope in writing this is simply that some of these ideas may help or resonate with other people, and that my voice can help fill the void that I mentioned earlier. And before I continue, I want to directly address that void.

In my little professional world (technology start-ups), nobody has written more about wealth and happiness as of late than Naval Ravikant and Daniel Vassallo. They are both fabulous thinkers on this topic—you should read their writing if you have not. I am a fan of both.

That said, they do fall on one end of the spectrum that I mentioned. Naval is an extremely financially successful CEO and investor, and he’s been very open about saying that for much of his life he worked way too hard, was extremely focused on becoming rich, and really burned himself out on the way to getting there. It wasn’t until he was financially wealthy that he started optimizing his life for his own happiness and freedom.

David’s story is similar, albeit not as extreme. He was making $500,000 per year as a software engineer at Amazon before he quite deliberately stepped out of the rat race. I admire that wholeheartedly. Today he’s working a job two hours per day that pays him $120,000 per year while he’s building a new home from scratch in a forest outside of Seattle. Kudos to him! My point here is just that that’s not terribly relatable to most people.

I’m not knocking Naval or Daniel at all—more power to them both and I believe all of their successes are hard earned. I’m just saying the vast majority of people who read their ideas react with a “Yea, that’s not exactly an option for me” or “You weren’t singing this tune until you were rich.”

I know I did.

On the flip side, I’d recommend reading The Art of Disappearing by Ajahn Brahm. This is an amazing book and introduction to Buddhism written by someone who decided to completely reject most societal structures and certainly the quest for financial wealth or material objects.

I think the ideas and perspectives presented by Naval, Daniel, and Ajahn Brahm are incredibly important—I’m just looking to fill the void between them, which I think is a far more relatable space for most people.

You know that you should “live in the present”—but why don’t you?

You don’t need me to tell you that living in the present is something we should all strive for, and a practice that’s tightly correlated with happiness. Our minds are constantly chasing wants, desires, and new thoughts—so much so that we miss out on what’s happening right in front of us.

I would not describe myself as a “meditator,” but the benefits of meditation are much less tied to levitating off the floor on your way to enlightenment and much more grounded in taking a minute to yourself to acknowledge the world around you. For me, this often just takes the form of taking a minute to watch the palm fronds rustle in the wind as I sit in my front yard with my kids.

While I try my best to incorporate those moments into my day, I am not particularly good at living in the present. It’s certainly something that I have to work at. But I think for most people, this is typically fueled by a need to go, go, go! They’re compelled to work harder, faster, to get a bigger house, to make more money. The “race” is what keeps them from slowing down, from living more fully in the present.

That’s not me.

Over the years I’ve learned to examine the defining aspects of my personality, and I have a combination of two personality traits that I think is quite odd.

First, I am good at not caring about “keeping up with the Jones’.” Most people I know struggle with this, but I really don’t. I’m the type that you could probably drop off on a deserted island with a pair of board shorts and a spear, and if I like the view I would be happy as a clam. If I’m happy with what I have, I’m happy with what I have— what you have has little impact on me.

Second, I am without question a “searcher.” I don’t look back very often, but I’m always looking forward. These two ideas seem to be diametrically opposed, and in some ways they are. But my searching is not a quest for bigger, better, richer—it’s a direct result of my happiness. I am always thinking about what’s next or what else is out there to experience, because I recognize that I have limited time and want squeeze everything out of life that I can.

This aspect of my personality makes it more difficult for me to live in the present. The only tip I have here is to look at the reasons that you struggle to find home in the present—the more that you can understand that, the easier it is to address. For me that means understanding that yeah, there are things that I haven’t experienced yet that I’m really excited about. But if I spend all my time daydreaming about them, I will miss what’s right in front of me.

Like the palm fronds in the wind and my kids.

Worry is the not-so-subtle killer of happiness

The only item in this post that I’ll say I’m really, really good at is not worrying about things that I can’t control. I think this is far more tied to our happiness than most people suspect.

Without question, this aspect of my personality is tied to my mother. My mom is the type of person who looks at the world with a lot of wonder. Our typical phone conversation consists of her telling me how beautiful the moon looked last night—but she’s also an obsessive worrier. I have watched worry consume her to such an extent that she’s enjoyed her life far less than she may have otherwise. I think that’s unfortunate, and I’ve probably overcorrected as a result.

Was her worrying justified? In some cases yes, in other cases no. It always came from a good place and was well intentioned, but that doesn’t mean it hasn’t been crippling.

There are lots of things that are worrisome, but if you can’t control them worrying about them serves absolutely no purpose other than to drive you mad and make you less happy.

That doesn’t mean that I don’t worry, but I very rarely worry about anything outside of my own control. It’s particularly relevant to this conversation that I do worry a lot about money—definitely more than I should! But this is something that’s in my control and while I agree that there are more important things to worry about, I reject the idea that money isn’t worth worrying about.

Money is the lifeblood of our day to day lives in modern society, and we all have a need for it at least to some extent. It’s much like oxygen to the human body—we don’t need unnecessary bounties of it, but you sure notice pretty fast if you don’t have enough to survive comfortably.

I’ve also noticed that I worry about money that much more since I’ve become a parent. Becoming a parent requires that you have more money to support a family, but beyond that my worry is driven by the realization that my decisions—including turning down opportunities to make more money and live more comfortably—don’t just affect me now but also my kids.

I’m using worrying about money here as an example, but the bigger point is simple—I think one of the most direct paths to happiness is learning not to worry about things that you can’t control. That’s easier said than done, but I think the cheat code is to appeal to reason. Sure, something may be worrisome—but if you truly can’t change it, you’re only poisoning yourself and your happiness by letting it consume you.

Distract yourself by addressing the stuff that you can control instead!

Consider the role of responsibilities in your life

This is kind of a funny topic and one I didn’t think about much until recently, but I think another step towards building wealth and happiness is considering the role that responsibilities play in your life.

Through most of my 20’s, I had a job but otherwise very few responsibilities. As time went on I folded in a serious relationship, a mortgage and other financial obligations, I had kids, and generally my list of responsibilities grew quite quickly. More people were expecting things of me, and I had obligations to meet those expectations. Some people will say “that’s just growing up,” and to a large extent that’s true. But I think it’s worth examining the role that responsibilities play in your life.

Some people truly love responsibilities—whether they recognize that or not. Many even need them to thrive! They want to feel like people depend on them at work. Their family gives them an enormous sense of purpose. The fact that they are needed and things are expected of them by others gives them on opportunity to deliver and feel fulfilled. Even as I write that sentence, I get it.

But for me personally, I hate most responsibilities. You may read that and say, “Well that’s just you being immature,” and it’s your prerogative to think that. I don’t hate all of my obligations by any means, but as I’ve folded more and more responsibilities into my life I feel like they’ve increasingly encroached on my personal freedom. With more responsibilities, you simply have less time left to yourself—I get far more fulfillment from having a sense of freedom than I do from successfully delivering on a laundry list of responsibilities.

At this point in my life, I’m actively looking to shed responsibilities whenever I can—it’s about having only a small number of the right responsibilities, and this practice and mindset is absolutely tied to my own happiness. In many ways I believe recognizing this and punting on responsibilities whenever I can is the “adult” thing to do.

My philosophy on investments

So far I’ve talked more about building happiness than the practice of building actual financial wealth, so let’s turn our attention there.

As I said earlier, I’d love to be rich!

While that’s the case, I’ve developed a financial strategy that I’ve heard exceedingly few people state outright…

I won’t make any investment solely for the financial return.

Hear me out.

I work in the world of technology start-ups, which is a pretty screwed up place from a financial perspective. I listen to start-up founders whine all day about how they can’t raise money from venture capitalists, then in the next breath they’re swapping stock tips. This is beyond screwed up to me—why would anyone invest money in your business, when you’re out investing money in public corporations that you have nothing to do with?

I understand not co-mingling your business and personal finances, but consider the message that this sends. If you’re unwilling to invest your own money into your business, why should anybody else?

At the moment, Bitcoin is the most representative example of an investment I just can’t bring myself to make. I think it will turn out to be a great financial investment, but Bitcoin provides absolutely no value to me or my life other than being a potentially lucrative investment. I just can’t bring myself to do it.

The stock market is similar. I watch friends spend countless hours studying the stock market and obsessing over their portfolio. It boggles my mind that people line up to invest their hard earned money in big corporations they know little about and certainly have no influence over. Not to mention there corporations most often don’t enrich their lives in any way—their interests are purely financial.

Let me be very clear about this—I have no issue with people making investments solely for the financial upside. I just choose not to spend countless hours researching or studying those opportunities, when that time could be better spent learning about investments that yield returns both in terms of happiness and financial gains.

I understand the importance of having a diversified portfolio of investments. And hey, if you’re already wealthy making investments that are solely financially motivated might make some sense. But that brings me back to the void that I’m looking for fill—if you’re not already wealthy, any investment that you make means that you’ve already invested your time and energy into saving up enough money to make the investment. Shouldn’t it be in something that provides a return not only financially, but also in terms of your happiness?

What this has meant for me, personally, is rather than investing in Bitcoin or the stock market I’ve invested in myself—primarily via my start-up.

  • This has the potential to be very financially lucrative.
  • This is already paying huge dividends in terms of my happiness—it’s enjoyable work and gives me a ton of flexibility.
  • I have a huge ability to influence the success of this investment.

How is such an investment not preferable?

The point here is not that everyone needs to start a company so they can invest in themselves; I’ve practiced this in other areas too. For example, I’ve always has an interest in real estate. But if I was investing in real estate solely to deliver a financial return, I’d probably buy some beat up duplex near a college in Kansas and rent it out as a slumlord to college students.

Instead, I’ve had a personal goal to own a small second home on a tropical island. Last year I bought the place—it’s a long term financial investment where someone else will end up paying the vast majority of my mortgage. But it’s also a place that I’ll get immense pleasure out of visiting for a few months each year—my family is heading to live in the property for three months this fall.

I’ll get so much more yield in terms of wealth and happiness out of this investment than I ever would by investing in that duplex in Kansas!

The luxuries of minimalism

Somewhere in the last decade, the practice of minimalism seems to have turned dirty. For many it conjures up images of a young unshaven man who owns one t-shirt and a single pair of shoes sitting in a 500 square foot apartment with only an Ikea table. Fair.

But I am at least a bit of a minimalist, and it’s absolutely contributed to my happiness in two ways.

1) First, owning less stuff does increase your personal freedom. It’s much easier for me to take off and go live somewhere else for three months this fall when I have a lot less stuff to account for.

2) Second, owning fewer things means you can spend more on the things that you do buy. Want to live a life of luxury before you’re rich? Buy less stuff. Most of the things I do choose to purchase I get really excited about because they are awesome and not just excess.

You only go around once…

Of all the cliches themes we’ve thrown around so far, perhaps none is more commonly stated and ignored than “You only have one life to live.”


This is alarmingly true—but just as so many people don’t prioritize their happiness and lifestyle until they’re rich, very few people choose to truly live life like it’s their last until they have some sort of serious health scare and confront their mortality.

Early on in my career I had the opportunity to work a guy named Josh Silverman, who is maybe 10 years older than me. He mentioned to me one day that he took 30 days off when he turned 30 and was planning to do the same, no matter what, when he turned 40, 50, and 60. That struck me as a really great idea.

My wife and I decided to adopt a version of this ourselves, and we both quit our day jobs in 2018 to travel for six months. We had the time of our lives, and vowed to do it every five years—we’ve already reduced that time frame to every other year. I’m in the midst of our second six month trek as I write this, from San Diego to Savannah to Cape Cod to Hawaii.

I’m fortunate to have the flexibility to work remotely, which will enable us to take this trip, but my wife is leaving behind a great job that she loves. Many of our friends think we’re kind of nuts… why would she leave a job she loves so much? What about insurance benefits? Our 401ks? The nanny that we finally found that’s so great with our kids?

Yes, we’re uprooting many aspects of our lives but consider the alternative—a life that you’re less excited about just because you’re too afraid to rock the boat? It’s cliche, but we won’t look back at our lives and remember those 401k deposits or the great nanny that we let go. We will, without question, remember the months we spent in Savannah, Cape Cod, and Hawaii.

It is that simple.

You can build both wealth and happiness on your own terms—if you just give yourself permission to do so.