I Don’t Have To

It was a revelation when I realized that I didn’t have to be unhappy to be an artist.

No one ever outright told me that this was a requirement — heartbreak or abuse or drama or whatever — in order to be a creative person worth the title. But it was implied by pop culture and hearsay. Great artists are tortured souls, I knew, and being a happy person, I felt I was at a disadvantage.

And so I sought out difficulty. I stuck with a few relationships long past the point when I admitted they were bad for me, and mined my life for something dramatic, something sad. It didn’t work very well, so I gave up on the whole artist thing for a while. Tempered my creative ambitions.

Designers don’t have this same cultural baggage. You don’t hear as many folktales about brilliant designers being gifted because of some horrible thing that happened to them. There aren’t any old wives’ tales about designers mailing their lobbed-off ear to someone before booting up a pirated copy of Photoshop. No popularized culture of self-destruction in the typographic field.

I was able to embrace design the same way I’d embraced art, but without those added expectations. I didn’t even realize the difference, really, until I was a senior in college, looking back at the work I’d done and recognizing that the things I made when I allowed myself to be happy was far more me than anything I did while feigning anguish.

I experienced a similar moment when I was on my way out of Los Angeles, leaving behind my brand-building lifestyle for something else, something new that I hadn’t quite defined yet.

There’s a culture of dominance in the entrepreneurial world that you don’t really notice, not so that you’d put a name to it, while you’re inside that culture. The heroes and villains and hero-villains in the entrepreneurial world are all larger-than-life caricatures who stomp around and tell all those backward, dust-covered tycoons, and normal people who lack their superhuman vision where they can stuff their caution and concerns. According to the folklore, entrepreneurs take up space, dominate the room’s attention, and have origin stories that are repeated in awed reverence by people who aim to make the same ripples in the world someday.

Stepping away from this culture for the first time since I started my first business as a teenager, I realized how much of this grandiosity I had faked for so long; how much of myself I had to set aside to fit this mold so that others would see me as someone who made sense within that context; would believe I was made of the right stuff for success.

Quite often the friendly, happy person is seen as a rube or as someone who’s not made of stern-enough stuff in the context of entrepreneurial culture, but that’s who I am. I like helping people out, I like being happy. I like building things that don’t scale to infinity and living a lifestyle that isn’t ostentatious. I don’t believe that being an asshole is an advantage, or an attribute worth bragging about.

I enjoyed those years of entrepreneurial ambition to some degree, but I didn’t realize what I was missing until I extracted myself from that culture, from those expectations and folk tales. As soon as I was on the road, unsure of myself but wanting to make something me-shaped, I found out that there were so many elements of who I am that I hadn’t been exuding in my work or in my own brand.

Recognizing that these expectations were a reality in these different spaces was a big turning point for me. Recognizing that I don’t have to live up to these expectations in order to participate, enjoy the work that I do, and thrive, was earthshaking. It formed the entire basis for how I live and work today, and allowed me to be more myself than I’d ever been before.

There’s nothing inherently wrong with any of these culturally prominent stereotypes.

If you want to take up space and stomp around and be seen as a hard character who gets things done, that’s wonderful. There’s a pre-built scene where you can do that.

If you’ve had some difficulties in your life and can tap into that heartache, that pain, that suffering, and channel it into something beautiful, something communicative, then I applaud your positive use of something negative. Keep it up! Make your art.

These ready-made cultures can be destructive, though, if we assume they are the only paths to success or fulfillment — if we feel compelled to whittle off our rough edges so that we better fit the commonly accepted perception of what a protagonist should look like and how they should behave.

Most of us are exposed to these pop culture idols before we’ve lived enough life to know who we are as individuals, so the likelihood of using these creations as shorthand, as filler until we better understand ourselves, is high.

Extracting ourselves from these preconceptions, then, and reminding ourselves that we don’t have to be anything that doesn’t align with our beliefs, our preferences, our ideal habits, is an incredibly valuable pursuit.


The Math

Any lifestyle is within reach. We just have to balance the books. Do the math.

In a lot of cases, this means tallying up our available resources and reallocating them accordingly.

You might want to write a book, for instance. Writing a book is typically a monetarily cheap endeavor, but requires a great deal of time. As such, you look at the time you have available — 24 hours each day, 7 days a week, etc — and sort out how much of that time you can dedicate to the writing of this book.

Most of us already have most or all of our time accounted for. We spend it at work, or on our habits or hobbies. This is where the seeming simplicity of the math falls apart: how do we choose between two possible ways to spend this precious resource?

We have to decide, then, what’s more important. Between writing this book and, say, binge-watching Netflix or playing board games with your family, which do you choose? Between writing your book and sleeping a little more each night, or working full-time at the office, which do you choose?

The trouble is that there’s no clear answer. Working is good because it helps us keep a roof over our heads and food on the table. Spending time with our families (particularly if there are board games involved) is good because these are (hopefully) people we enjoy spending time with, and we want to prioritize happiness in our lives. Sleep is good because it helps us stay healthy and mentally alert. Even binge-watching Netflix can be good, when it’s part of a balanced (or intentionally imbalanced) lifestyle.

In this case, then, we might start looking at other ways to make those numbers dance.

Perhaps we figure out systems which allow us to do our work more efficiently, and which free up a few minutes each day. Over time this might liberate more time, say an hour or two each week, which we can then spend on our book.

Or maybe we reduce our monetary needs, moving into a smaller space, eating more simply, living with less stuff in favor of liberating more time. This might mean working part-time, instead, which frees up many previously entangled hours to spend however we like, possibly on that book.

Or maybe we step away from TV for a bit, to focus on this book. We decide to take two months for a lifestyle experiment during which we’ll dedicate all of our spare time to writing instead of consuming.

Perhaps we’ll attack this from the other side. We can write in short bursts each day, a few minutes here, a few minutes there. Because of this practice, after several months we are able to write more, and better, in less time. This means that each liberated minute is more valuable in the pursuit of this book-writing endeavor.

It could be that we already have some time freed up, but it takes ages to get into the right mindset and focus on the task at hand. Spending some of that time on working out, instead, could be the right move. Maybe a healthier body, feeling good more regularly, could allow us to be more in tune with ourselves and as such, more capable of stepping away from the everyday stresses into a more productive mind-space.

Or perhaps the same movement but with meditation or some other mind-focused ritual. Perhaps you’ve freed up an hour each day, and you spend ten minutes doing jumping jacks and push-ups and stretches, ten minutes sitting quietly, doing nothing physical at all, allowing your brain to sort itself out, and then use forty minutes to sit in a chair and write, the internet turned off, as many distractions as possible kept out of reach. Though this is a deviation from the ‘free up as much time as possible to write’ methodology, it’s a combination approach that could lead to more and better words landing on the page, faster.

The path to achieving a certain lifestyle or goal, then, isn’t always a straight line. It’s something with an infinite number of variables and with uncountable legitimate paths that will take you there.

It helps to sort out the math, though, to juggle the numbers so that you’re aware of what variables are in play, and so that you don’t feel these goals are impossible tasks.

Piece by piece, pick apart what’s in your way, sort out what’s necessary and what’s just habit, just a psychological barrier that can be overcome, and then start moving toward where you want to be.


Seeds and Vegetables

One of the questions I’m asked most frequently is about making money while still being able to enjoy a fairly liberated lifestyle.

Asking “How can I make money so that I can live such-and-such lifestyle?” however, is prioritizing money before life. It’s like being born with a barrel full of seeds and asking how you can sell them to buy vegetables.

You are born with your energy, attention, and all of your time. Over the years, you learn to exchange these things for money.

More ideally, we ask ourselves something like “How can I sustain this lifestyle that I’ve built?” because this implies that we’ve figured out how we want to live, first. From there, we take into account the economic realities that shape our environment and see how we might perpetuate the life we’ve already built (or have started building). This is the equivalent of planting those seeds, digging some irrigation canals, and trying to decide how to invest the fruits (and veggies) of your labors.

The advice that I usually give in response to this question is:

Start building the life you want, today. Avoid inessential commitments, make a lot of valuable mistakes, appreciate any privilege you might have, and help others along the way when feasible. Then, figure out how to sustain your lifestyle, knowing something of how you want to spend your time and energy, what rewards will actually fulfill you, and what you’re willing to trade for more opportunities (and what you won’t trade at any cost).

Flipping this, selling your time, attention, and energy first, is like selling off your seeds in hopes of being able to someday afford vegetables. It’s a shortcut we’ve been trained to see as the default option, or even the only option, but this couldn’t be further from the truth.