Bob Marley (supposedly) said that “some people are so poor, all they have is money.” What he meant was that there are people that mistake the pursuit of wealth for their purpose, and when they realize that they’ve conflated the two, they understand that they’ve missed the point of why life is so worthwhile in the first place.

This is why purpose must be discovered without the promise of incentives or monetary rewards. It can only come from conducting an honest audit of what makes you feel wonderment (i.e. childlike curiosity) or a sense of duty (i.e. parental responsibility), and then directing your attention to making the most of those endeavors.

The sense of self-worth that can be derived from purpose is free from money’s clutches, so keep this in mind whenever you feel discouraged by how much you have. Money is simply not a variable here, and the knowledge of that goes a long way.

I’ve spent the past six months of unemployment conducting the audit described above.

And I’ve learned that what brings me wonderment is learning how technology works¹, and my sense of duty is in teaching others how to use it.²

It’s not so much that I forgot those things about myself. What brings me such shame is the fact that I’ve suppressed the urge to pursue those activities in the name of making money.

Ultimately, love is the thing that matters most, but it’s often overlooked and disregarded as a cheesy emotion. In the minds of many, skepticism signals intelligence, whereas love signals naivete. After all, you garner respect by sounding the alarm on humanity’s problems, and not by pointing to love as the answer to them.

This is precisely why love is taken for granted. Even if love is felt between you and another person (be it a friend, partner, family member, whomever), it’s often left unarticulated because saying “I love you” means that you’re fine with seeming naive and aloof. And if this fear goes on long enough, you’ll feel that the best way to express your love will be through ways that act as surrogates for it.

Another thing I’ve learned about myself is that I am a naturally trusting person.

The majority of people I’ve encountered professionally appear to be the opposite. In particular, those playing the entrepreneur game seem especially skeptical or fearful of leaning into love.

Skepticism and fear drive those folks to make decisions about their business which ultimately lead to their demise.

I’ve sat in countless meetings with teams of executives who are frantically trying to come up with an idea for how to get more people to buy their thing.

At some point, an obvious answer emerges which involves building something that genuinely helps people.

But that obvious answer is almost universally looked at the same way you’d look at a plate of boogers because of financial concerns.

This general feeling is why I’ve struggled so hard to find a job. I’m tired of building software which only serves the purpose of making money.

Instead of jumping into another job where the culture is driven by money, I’m waiting until I come across a culture that is driven by love.³

Money’s a great tool, granting me a level of freedom that I may not have experienced had I pursued any other career.

But money is also the primary reason why I am dealing with severe anxiety and depression. It’s why my heart constantly feels like someone is squeezing it like a strongman squeezing an orange.

The only thing that causes the grip to be released? Doing things that lift the “purpose” and “love” levers. It’s when I trust others and spread as much love as possible when I feel the most alive.

Using the analogy in this article, I’ve spent the last 12 years of my life optimizing for the money-receptive levers. I’m gonna spend the next few in pursuit of lifting the money-negligent ones instead and see where that leads me.

So then I asked him: what kind of VC does he actually want on his cap table (that is, owning a portion of his company)? What would be true of the sort of investor who really gets him and resonates with what he’s building?

The same question applies here as on a first date, I pointed out: do you want them to fall in love with you, or with a fake version of you that you now either have to maintain—at the expense of the person you actually are and want to be—or else face irreconcilable conflict and disapproval when you finally drop the facade?

You want to reach the investors in the room who want to flame-spot audacious and idealistic young upstarts like you; who’ve staked their careers and reputations on the thesis that the world needs more of just the kind of company you’re building; who resonate so hard with your story and are so wowed by your talent that they’ll be willing to invest in, nurture, and protect your agency as a founder.

One can of course relate to money in pathological ways. For those whose standard of value resides not in a conception of their fully-lived life (a la the builder), but in the impressions or judgments of others (be it God or society or their parents or some other “drill sergeant”), money means whatever it purportedly means to those others—status, in some circles, or wicked materialism in others, or in still others, “privilege” to be forgiven with obligate philanthropy. 

By contrast, a builder’s relationship to money is not mediated by any of these external intermediaries. She understands that money is a medium of value exchange, and what she values is set by the life she wants to build and the world she wants to live in. 

There are also simpler pathologies, such as when fear or insecurity drives founders to pursue short-term monetary gains over the longer-term health and durability of their business. But such financial anxieties can be diagnosed and remedied by re-orienting toward the overarching goal of building one’s best life, which presumably includes a healthy and durable version of one’s business (or whatever one is building) as part of it.

Quite a useful way to reframe money and its importance to a well considered life.

Nathan Barry of ConvertKit fame shared this post on Reddit a few weeks back, and I have read it a half dozen times since then.

If you are at all interested in taking the leap into being an entrepreneur, read this. It’s more insightful and inspiring than 90% of the business books I’ve ever read.

Jason Fried is always a fascinating and insightful person to listen to, and this interview is no exception. He has a lot to say about how awful work can be (but doesn't have to). I'm definitely going to read his new book as a result of listening to this podcast.

However, what really got me thinking after hearing this podcast was the way that Jason uses his strong, personal convictions to run his software company, willfully eschewing the conventional wisdom that comes out of Silicon Valley.

I've long held the opinion that raising large amounts of money confuses me. I've always thought it was because I didn't truly understand how investing and finance works, or maybe it was because I bootstrapped all of my businesses and wasn't aware of a different way.

But after listening to the way Jason justifies the decisions he makes with his company (not having a bunch of benefits that keep people at work, paying for people to go on vacation, etc.), it made me smile and think about some of the decisions we've made at the JMG, and how the vision of the company I want to run does not need to fit the mold of the typical software company.

When running a company, it's crucial that you listen to your own gut and to skate to where you think the puck will be.

After all, isn't that what entrepreneurship is all about?

There were a ton of valuable takeaways from this episode of The Tim Ferriss Show featuring an interview with Seth Godin.

• That concept of "be a professional, not authentic" was quite eye opening. I had orthopedic surgery not too long ago, and it truly would've been a bummer if she decided she didn't feel like cutting my knee open that day.

• I've had my own existential qualms about selling apps because, at the end of the day, does anyone really need an app? However, much like scope creep, you can find a way to spin it into a positive for everyone involved. It’s okay to sell people something you think they don’t actually need, because they actually do need it. Be empathetic and sell to what people think they need.

• You get better by serving your smallest viable audience. If you keep trying to make things work for folks who don't fit that niche, you are just doing a disservice to those who do fit your niche.

If you run a company, this is required listening.