Back when I was 24-25, I told myself that our brand new baby business would be doing $1-2 million a year by the time I turned 30. My 30th birthday is Sunday. Did we make it?

Nope.

Am I sad?

Nope!

So, should I then be giving thanks to the overweening power of subconscious self-protection mechanisms?

Nope!

There are a lot of lessons I’ve learned in the past 6 years of running a bootstrapped product business, ~18 years of hustling, and 4+ years of teaching others to hustle.

And this here lesson is a major one:

You can never know quite how things will turn out…or how you’ll feel about it when they do.

The thing you think you want on Day 1 will very likely turn out to be the last thing you’d want on Day 731. The vision board you set your eyes & heart on may turn out to be something you despise.

Or, more likely, something that just doesn’t matter to you any more.

For me, the $1-2 million was a kind of signal: I have ambition. When I talked about “competitors in our space,” I used to gasp at their audacity (because of how terrible their products were). I knew I could & should do better.

My friends often heard me laughing, “I’m gonna eat their lunch!”

That was 5 years ago. Today? I just can’t give a shit.

In 2012, we grossed about $750k, between Freckle Time Tracking, 30x500 Product Launch Class, our various JavaScript-y technical workshops & ebooks. We could have made it to $1 million and beyond in 2013-2014, if that was what really mattered.

We worked on a second SaaS that people absolutely loved, that earned five figures in private beta, that looked like it was going to be a huge hit. We could have eaten ZenDesk’s lunch, if that was what really mattered.

But it isn’t.

That’s why in 2013 Alex, my 30x500 co-teacher, and I decided to kill the goose that was laying $200k golden eggs. Yeah, we took the class that brought in >$400k/year and…ended it. We started fresh. We retooled the class, giving up $320,000 in revenue. And it was worth it.

These days I’ve got less than zero desire to “beat” anyone. I don’t want to eat their lunch. I just want to eat my lunch. At that awesome local cheese shop. In the courtyard. With my team…my friends. Without concern for the hour or duration.

And I don’t care if we never gross $2,000,000 a year.

Yes, this sounds like the last page of a chick lit paperback. But it’s true.

A fuckload can change in 6 years…and it usually will.

In those past 6 years I left a consulting company I co-founded, convinced my husband-to-be to leave his consulting agency that he co-founded (and start a new one with me), convinced him to start a product company with me, and did all the things that entails.

That included those times when I/we…

  • moved to Austria, got married, moved again, moved back to the US
  • forged a development partnership, only later to kill it
  • and another (later) went the same way…
  • designed and managed the development of a SaaS, and learned how to run one
  • prodded, structured, wrote, laid out, and launched a technical ebook
  • designed & delivered 2-3 day private JS workshops
  • took those workshops on the road, turned them into public events, then took them online…
  • launched a 3-month email class with only 1 month of content pre-written, then redid it the next time, and then redid it completely again (years later)
  • hired / fired employees, freelancers, partners, several times…
  • created & ran a bootstrapping conference, and again, and again (the 3rd one is this May 29-30! and sold out, naturally)
  • started a second SaaS…paid a lot of money for development help…tried to create a partnership…built it up in revenue-producing private beta…then killed it
  • got my husband a green card, moved back to the US, bought a house
  • hired again…slowly…keeping everybody this time
  • started to work on a Real Book™…

Yeah. I’ve been around the block. Many times. Believe it or not, I left a bunch of shit out. (Including all the things I learned watching my friends do.)

The biggest thing I left out of this timeline is this: At the end of 2009, I developed a chronic illness.

When it was waning, I was okay…low-capacity, maybe 20-50% of my normal abilities, and everything took serious, draining mental effort, but I could work. I could get things done eventually.

But during the periods when it was worse — often caused by that effort — I could barely think. I could barely get out of bed. That’s not an exaggeration; standing up often made me so dizzy I had to sit back down again, and often the most exercise I’d get was going from the bed to the sofa and then back again at night. That went on, in cycles, for years. I’d be able to be myself (if diminished) for a day or two, and then I’d pay the price. There were times when I didn’t leave our apartment but once in a month. I kept trying & trying with research and different doctors, and every now and then I’d find something that’d help a little…but until late last year, nothing truly helped.

Every so often the weight of it all would crush me so hard I’d stop whatever I was trying to do (like tying my shoes), and sit, and cry, because my life was over.

It sucked beyond my ability to describe it. And, with the exception of my husband, I was almost totally isolated, in a foreign country.

It changed everything.

Tragedy is so often the turning point of a story. It’s a cliché that a crisis shows a person what really matters. But guess what? Clichés are clichés for a reason.

All this, good and bad, taught me what’s really important to me:

It’s not “beating” everyone, or even someone.

It’s not about domination, or even winning.

It’s not about perfection, or even completion.

It’s not about other people telling me how good I am, or even how good my work is.

It’s not about rewards or status, or even recognition.

It’s not an arbitrary amount of revenue or number of employees.

It’s not — and this is a hard one to swallow, but bear with me — even about keeping my word.

Going through months at a time of being unable to work; having good days and knowing that a good day now meant suffering tomorrow; having to continuously cancel things I said I’d do, for others and for myself; being isolated in a country where it is nearly impossible to form deep, caring relationships with new people; having hired people because I thought we needed to do it, and suffered through the emotional wrench of firing people who had to be fired; designing and building an app that people loved, that people paid for in beta, that people clamored for, that we didn’t want to run; well, that was an accelerated crash course in What The Fuck Actually Matters!?

And the answer is: Not a lot.

I learned that these things do not matter, not even a little.

Imperfection doesn’t scare me. Incompletion doesn’t scare me. Less than my best work doesn’t scare me. Customers do not scare me. Launching, shipping, canceling — they’re old hat to me now. Once you face the specter of your life being nothing but an endless parade of empty suffering, everyday things hold no more fear.

Yesterday at the custom cocktail tasting for the next BaconBizConf speaker’s dinner, I said to Alex, my co-organizer and co-30x500-er:

“I’m almost stressed about how not stressed I am about this conference. Maybe? I dunno.”

Now, if you’ve ever known a conference organizer, you know they tend to be harried. There’s a fair amount of stuff to do to pull off even the simplest conference. It feels like we’ve left some of the organizational details too late. Hey, the conf is in 20 days, exactly, and we are just hammering out the final details now. All very chill. Maybe terminally chill.

But, in reality, I just can’t convince myself to be frantic. I know, deep down, that it’ll work out just fine. I’m not just lazy, I’m laissez-faire.

This is the third conference we’ve run. Each one has made its attendees very happy. I could practically do it in my sleep. With nothing.

Even if the biggest moving parts — the caterers — failed us all at once, things would be fine. We’d order pizza or sandwiches. People aren’t coming to our conference for the food. Video guy canceled on us too? Oh well, we don’t need video. The event could continue, even if half of our headline speakers canceled on us at once.

Last year it was Surprise!! 95 Degrees and we had to cancel our very cool 2-hour walking tour at the very last minute. No big deal. You know what we did instead? Teardowns. It wasn’t even our idea. And it was awesome.

That’s my approach to life now: “It’ll be fine.” Very little in life is unrecoverable. Very little in business is permanent. Very little is world-ending.

I do try hard. I do my research. I revise, I improve, I kill what’s not working. I pick my #1 and #2 priorities, and I go at them, and do the best I can at the time and with the resources & energy & time I have available.

I design & structure my work to have a lot of things that are nice additions, but not world-ending if they fail. I design my life that way, too.

Everything I do is designed to deliver the most impact for the least work, with the fewest points of failure, and the slightest requirement of perfection possible.

Everything else I let go. I just don’t care. Don’t have the energy to care. Or actually, now that I do have the energy to care, I simply don’t.

And this works out fantastically for everyone involved.

Because you know what really matters to me?

My husband. My friends. My enjoyment of life. My community. My house. My cats.

Then my customers.

My customers, my students — and you know I love you, but really — my customers come last.

Which is exactly how it should be, because it’s all the other things that give me the energy & the will to show up and deliver for the customers.

If I put my customers first, everyone would lose. That’s a recipe for loss, stress, and ironically, reduced ability to serve others effectively.

So I put them last, and everybody benefits.

This is what I call “Oxygen Mask Entrepreneurship.” I put on my own mask before assisting others. Every time. Without fail.

It’s hard to learn this without a crisis, without a chronic illness, without a tragedy, I think. You can’t know just how much of your own trouble you make for yourself, and how manufactured & unreal all the drama is. How unnecessary & self-flagellating the constant stress and crippling sense of responsibility. How the most important things are the ones that are easiest to neglect.

I’ve seen what happens when all that pretense falls away, because I couldn’t, simply physically couldn’t, do it any more. And guess what? Nothing bad happened. In fact, that’s when I did some of my best work ever.

So, that’s why I can’t be bothered to get emotional about the revenue, or even the milestone birthday, or how fast Freckle is growing, or if there are a couple hiccups in our video lessons. Goal? What goal? Oh yeah, that goal I wrote in my journal in 2009. It seemed so important at the time. Ahh, but does it materially impact my happiness today, tomorrow, next month? Does it matter at all for my customers, even?

Nope.

I’m able to live the life I want to live, to spend time & work with people I care about, and help create fantastic results for my customers…without the rollercoaster ride. Without a 40-hour work week. Without the sturm und drang. With a smile on my face.

That’s what I call fine.

(And with that, I’m off to drink birthday margaritas. Have a nice weekend!)

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