How I run my business solo, without burnout

“Do you know how much more successful I would be if I had a wife?!”

This is one of my favorite lines from Ali Wong’s Don Wong special. I think about it regularly.

It’s well documented that the best thing a man can do for himself is to marry a woman. And the exact opposite, to the exact same degree, is true for heterosexual women.

Don’t we all want a wife?!

Sociologists call it the “Marriage Benefit Imbalance.” That’s a polite, sanitized name for a very harsh reality:

Heterosexual married women, on average, live shorter lives, have less money, more illness, more stress, are more likely to die by suicide, and face greater risk of violence (usually at the hands of their partners) than single women.

While married men?

Those lucky guys make more money, live longer, are physically healthier, and happier.

Sounds pretty nice.

Like Ali Wong, I’ve often joked that I wish I had a wife. Not because I want to get remarried — far from it. But I do sometimes long for that kind of support.

Since I don’t have a wife, AND I’m more focused on profit than revenue, I’ve had to figure out how to run my business entirely on my own.

Not a boss

When my son was little and I was truly drowning in my business, I tried hiring contract designers.

I went through more than half a dozen young people, all 20-something millennials (those kids are now in their 40s btw). It was shocking how hard it was to find someone who was good, affordable, and responsible. The word “deadline” didn't seem to be in their vocabularies.

I discovered through that process that I REALLY don’t like managing people. It never felt profitable or worth the headache. If taking on more work and bigger clients meant hiring people, I decided I didn’t want it.

So for a few years, I stepped away from my business entirely.

Retainers? No, thank you.

When I came back, in preparation for my divorce, I rebuilt with retainers. That gave me regular income, but retainers can sometimes provide a false sense of security and freedom.

It's hard to take a vacation when clients expect you to be available because the work is ongoing. And when my long-term retainers ended, I was left flat-footed, with a shriveled network and no safety net.

Now, I want to be fair: retainers aren't inherently bad. Done right, ongoing work can be a healthy part of a thriving business, as long as no single client accounts for too much of your income. Which brings me to the big no-no I committed: I let one part-time retainer quietly grow into a near full-time role. If one client is more than 50% of your income, that's not really a business. That's a job without benefits. Which I learned the hard way when my biggest retainer ended in 2023.

But even setting that aside, while I understand why retainers work well for others, I've made peace with the fact that they're not for me.

Real freedom

Switching to time-constrained, project-based work has made the biggest difference in running a successful solo business.

All of my projects have clear start and end dates (usually just 2 weeks). So now I can schedule work around my life, not the other way around. I take real vacations. I step away from my desk. Nothing falls apart.

I also stopped doing free proposals, which are one of the biggest time sucks for small businesses.

Instead I have a paid discovery session called the Branding Roadmap. It does the heavy lifting of scoping a project, but it’s so much more valuable than a proposal (which is really just free work that may never turn into anything). It builds trust, provides real strategic clarity for my clients, and gives me everything I need to deliver a stellar custom brand.

I lean hard on technology.

My Dubsado CRM (hooked up to my Quickbooks) is basically my VA. It tracks leads, manages my projects, handles contracts and invoices, and takes care of my bookkeeping. These two tools remove most of the manual b.s. of running a business.

I also have templates for every email I send repeatedly — onboarding, client wrap-ups, testimonial requests, networking, referral outreach. Some live in Dubsado, the rest as saved signatures in Apple Mail. Why reinvent the wheel every time I need to send an email?

And of course AI. Mostly Claude, a little ChatGPT. I primarily use AI for brainstorming and organizing information. I don’t use it to write for me because it tends to strip all the life from my words. And I’m still really not impressed with its critical thinking skills. BUT I love spitballing and iterating with it. I’m never just staring at a blank page anymore and I think it helps me write faster? I tell myself it does anyway.

Solo doesn’t have to mean stretched thin or burned out. 

With the right systems in place, being solo can just be about freedom. And we like freedom.

Goodies Just For You

WHAT I’M THINKING ABOUT: I’m probably going to do a whole email about it, but I really enjoyed Ezra Klein’s conversation this week with Jack Clark, the co-founder of Anthropic. They were talking about the rise of AI “Agents” that are able to do autonomous tasks. But there was a ton of interesting stuff in there about the importance of taste, intuition, and hard-won expertise, and why those are the last things AI will be able to replicate. It’s a long one, but I recommend listening to the whole thing.

WHAT I’M MAKING: On Sunday I made the NY Times’ Braised Pork Arrabbiata and had dinner for 3 nights. It needs to braise for a few hours (hence Sunday), but the prep couldn’t be easier. The first two nights I served it on pasta (it’s also really good on polenta). The third night, I didn’t think there was quite enough meat left for a full meal, so I served it on cheese tortellini and added a little pasta water to the sauce for more coverage. It’s so delicious, no one was tired of it by the third night. 

WHO I’M ADMIRING: Are you tired of custom proposals and want to build your own profitable, scalable offers? My friend, Jay Melone, helps you develop entry-point offers that attract premium clients and sell for you. We’re very aligned. I refer people to him all the time. He has a free masterclass on March 18 that you should check out! Get more info and submit a free invite request here.