Don’t Burn Down Your Business Yet

Entrepreneurs get the itch to make changes when nothing in the business seems to be working. That’s natural. Doing nothing would be, by definition, insane.

I get itch and a second one: I want to make changes when the business is working.

That second itch has two main causes, an addiction to chaos and an aversion to boredom. Left unaddressed, both of these tendencies become forms of self-sabotage. They have hurt my business, and my livelihood and family by association.

I think of these two tendencies as crusty knots in my psychology that I need to unravel and understand so that they no longer come between me and two things that most entrepreneurs want—deeply meaningful work and long-term financial stability.

I can pinpoint the exact moment that I first recognized my addiction to chaos. I was reading Dan Martell’s book Buy Back Your Time, and I came to this passage:

“Entrepreneurs can also become so accustomed to stressful and unknown environments that they become downright addicted to chaos.

Chaos can feel so normal that calm can actually feel strange. Entrepreneurs have been so trained in dealing with stress, like making difficult decisions based on incomplete information and last-minute changes, that they’re always looking for the next problem, even if it doesn’t exist. Without a fire to put out, they can grow inwardly anxious.” (51)

“Oof” is the involuntary sound you make when some bully punches you in the stomach. That’s also the sound my poor, unprepared mind made when Martell’s observation hit it.

I claimed to want peace, but my business ventures stretching back to 2009 told a different story of self-inflicted stress and disorder. I had a tendency to fix things that weren’t broken, stop doing what worked, and generally not leave well enough alone, as we say in the South.

I probed for threats, problems, and weaknesses and believed that this is what a responsible entrepreneur does. When he founded Virgin Atlantic, didn’t Richard Branson buy an airliner he could return within two years and say something like “protect your downsides”?

We get in trouble when we take good advice out of context, and if you had asked me, I would have defended my chronic overthinking and frenetic learning as being “strategic.”

I wasn’t being shrewd or strategic as much as I was looking for the miracle business cure, the crucial insight, tactic, or relationship, that would cause my problems to vanish.

The assumption that the answer to my woes was out there, not right here, caused me to discount what I already had in favor of more, new, and extra. Surely, the odds would tip in my favor. (Pro Tip: You don’t need the odds if you wear out the fundamentals.)

This way of thinking, driven by an addiction to chaos, caused my priorities to shift constantly. Too many projects competed for my attention, and no matter how smart or capable an entrepreneur may be, we don’t get very far if we try to go twelve directions at once.

A fraction of focus means a fraction of progress. This is math. Or science. Or Oprah.

The lack of meaningful progress fed my anxiety. “I’ve been working so hard, and yet I have so little to show for it.”

Don’t get me wrong. I had modest successes along the way. A silly mustache-themed photo booth app grew into a $250,000 side hustle and a tiny exit. A conversation at a farmer’s market led to a tech startup. My co-founder and I did the incubator, accelerator, and fundraising rodeo. I parlayed the startup experience into growth strategy and consulting. I’ve helped one of my consulting clients, an e-commerce company, build a brand and grow it past $2 million.

My wise wife reminds me of these accomplishments even when my ambition dismisses them as false summits.

If I listened to her more, then I would have overcome my addiction to chaos sooner. I wouldn’t see so many instances of the cycle repeating: get some traction, second-guess my path, change my mind about what I should be building or doing, start over without cutting existing commitments, take on too much, and make excruciatingly slow progress.

When my self-inflicted, anxious chaos didn’t bite me, my boredom did.

The irony is that small businesses start to feel boring when they start to work:

• You charge a profitable price.
• You deliver the desired outcome.
• You figure out how to get new leads.

Even working businesses still have problems because every business does, but its revenue model and core value proposition are no longer a Rubik’s Cube. Or rather, they are one that you can solve with your eyes closed.

I’ve gotten to that place of predictability a handful of times, and then that second itch would show up. Like a petulant Roman emperor, I would yawn, give a lazy wave, and say, “Next. I want to be entertained.”

Perhaps I’m too much a product of my elder Millennial generation because I believed that my work should entertain me. I was supposed to follow my passion. If you love what you do, you’ll never work a day in your life, right?

I had the freedom to bend the trajectory of the jobs I created for myself toward the trajectory of my passion, so shouldn’t I exercise that freedom?

Yes and no.

Yes, we should try new things in the same general direction. That’s called innovation.

No, we shouldn’t expect our businesses to provide a nonstop drip of creative and intellectual stimulation. That’s not its purpose. Its purpose is to create a livelihood.

Most people use the words “work,” “livelihood,” “job,” and “career” interchangeably, and this causes confusion because sometimes entrepreneurs think we’re optimizing for one when we’re really optimizing for another.

Clear definitions for work, livelihood, job, and career become very important:

• Your work is what you accomplish in your lifetime—your life’s work.
• Your livelihood is how you make money and pay your bills.
• Your job is the specific set of roles and responsibilities you have. It may include a title.
• Your career is the jobs and roles that you’ve had.

Some people work but don’t have a job. For example, my friend and mentor Bruce is technically retired, but he still advises CEOs and young entrepreneurs and helps nonprofits when they need a fractional CFO. He would tell you, “It’s fun.” We want to keep working when the work is fulfilling. Why would we deny ourselves the pleasure even after retirement?

Some people have a livelihood but no job. They live off income from other people, savings, investments, inheritance, social security, companies that they’ve built and fired themselves from, or some combination.

To create a livelihood for my family, I started various business ventures and side hustles. Most of them created a job for me. Each job came with some roles and responsibilities I enjoyed and some I didn’t.

But a business doesn’t care what its owner finds distasteful or tedious. It doesn’t stop having problems or needs because the owner is bored. It simply keeps acting according to its nature the same as a cat.

• We ought to find work that we love because fulfilling work is one of life’s greatest gifts.
• However, our work, our livelihood, and our job usually don’t overlap perfectly—at least not for a long time.
• Some of us need to admit our discontentment with our work. In “How to Do What You Love” Paul Graham would tell you that acknowledging your discontentment puts you “a step ahead of most people, who are still in denial.”
• Some of us need to address our addiction to chaos and aversion to boredom. Otherwise, our desire to feel passionate will continue to endanger our livelihoods.

Most of my entrepreneurial endeavors have been attempts to break the relationship between time and money and free up more of my time for the work I wanted more of—namely, writing fiction, nonfiction, and poetry.

Meanwhile, my family of five did need a livelihood.

So I always felt like an artist-entrepreneur or entrepreneur-artist—which identity was foremost? I didn’t know—trying to ride two horses pulling apart. The horses were those desires I mentioned, deeply meaningful work and long-term financial stability.

Though I can’t say I’ve got it all figured out, I can say that the business that represents my livelihood doesn’t need to entertain me. I can get my entertainment elsewhere. Taking my business in a new direction is exciting, and it can cause whiplash.

Following some hand-wavy passion doesn’t feel so noble, wise, or light when I’m wondering how I’m going to cover my mortgage payment and I feel that subsurface churn of stress and anxiety.

My business was never supposed to entertain me. It was supposed to create a livelihood.

Now that I better understand my own misplaced expectation, I’m ready to accept some monotony and boredom if that means a predictable livelihood.

I can see the choice in front of me:

• I can go get a full-time job, which I still don’t want.
• Or, I can change my relationship with my own business and figure out the systems, support, and sales that remove me as the bottleneck to growth.

That is the job to be done, and doing it well will ensure that I have more time to spend on the work I find most meaningful, some of it inside the business and some of it outside.

What I’m trying to say, my entrepreneur friend, is stop scratching the second itch. Wean yourself off chaos. See the long-term opportunity in boredom.