Your Business Looks Successful. Do You Like Your Life?
I want to have an honest conversation about what the fuck we’re calling success.
Because a business can look successful in all the ways we’ve learned to recognize. You’re booked out. People want your work. You have a good reputation. Money is coming in. From the outside, things look great.
But you’re also maxed out, stressed about taking a day off, and trying to work through being sick because the whole thing depends on you showing up regardless of what’s happening in your life.
I think we need to be able to talk about that without immediately turning it into a gratitude problem.
You can appreciate your clients, love your work, and recognize that the way you’re running the business feels fucking awful.
Demand tells us people want what you sell. Revenue tells us money is coming in. Neither tells us enough about the life you’re living while you produce it.
And before we decide that someone is successful, I think we need to ask what success even means to them.
We already know we hate these working conditions
We criticize employers for expecting people to work through illness, treating family responsibilities like an inconvenience, and acting like every employee should have the same energy and availability every single day.
We know how shitty it feels when taking a day off comes with guilt, or when being good at your job means getting more work until you can barely keep up.
Then we start our own businesses and find ourselves doing some of the same shit.
We don’t account for sick days. We fill the calendar without considering what the work will take out of us. We treat every available hour as an hour we should be able to produce something, and then get frustrated with ourselves when our bodies or lives interfere with the schedule we created.
Sometimes we become the boss we would have hated working for.
I feel like people do this because these expectations are familiar to us. We’ve spent years learning to associate being busy with being valuable and pushing through with being committed. Those ideas don’t suddenly disappear because we’ve decided to work for ourselves.
There are also real financial pressures involved. Bills need paying, clients need their work, and taking time off can directly affect revenue when you're the person responsible for selling and delivering everything. It's not as simple as deciding you're never going to work when you don't feel like it.
But I don't think we should accept harmful working conditions as the inevitable price of having our own businesses, either.
Especially when being the person imposing them on ourselves doesn't make them any better.
Booked out for what?
Being booked out might be exactly what you want. You might love a busy season, enjoy the work you're doing, and make enough money that the commitment feels completely worthwhile.
Great. I'm happy for you.
But being booked out doesn't tell me much about whether the business is actually doing what you need it to do.
What are you booked with? What does that work require from you? What does it leave you with financially? And perhaps most importantly, do you actually enjoy the life you're living around it?
If your calendar is full and you're still stressed about money, that’s not sustainable at all,…. If the revenue looks impressive but you can't be present for the people you care about, that also isn’t sustainable.
We shouldn’t have every good month requiring you to spend the next one crawling out from underneath the delivery and you don't have to disregard those things because somebody else would be absolutely thrilled to have your client list.
We're very comfortable celebrating the parts of a business other people can see. The bookings, demand, revenue, recognition, and all the other things we've collectively decided indicate that somebody is doing well.
But I want us to be equally interested in whether the person running that business actually likes their fucking life.
Mine is pretty straightforward
The most important thing to me is being home for my family.
I want my family taken care of, and I want to be able to take days off without stressing about work. I also want to have fun and help people.
If I'm having fun, helping people, and our family's bills are getting paid, that's what the fuck is up.
That doesn't mean I'm never going to want more money, a bigger business, or new opportunities. Those things could all be wonderful additions to my life, and I'm not opposed to any of them.
But I do want to understand what they're going to ask from me before I decide they're things I should be working toward.
I don't want to spend my time achieving things that look impressive to other people if doing so makes the life I actually care about harder to live.
That's my version of a very good life. It doesn't have to be yours.
Maybe you want to build something enormous. Maybe you want to work four hours a day and spend the rest of your time doing literally anything else. Maybe you love being busy, traveling for work, or having a calendar full of people and projects.
I don't think there's one correct answer here, and I'm certainly not interested in deciding what somebody else's life should look like.
A very good life means whatever the fuck you want it to mean.
The point is that you get to have priorities of your own, and those priorities deserve to matter when you're making decisions about your business.
The business is one slice of the life
I keep coming back to this because even the way we talk about business tends to put it at the centre of everything.
We ask what the business should leave room for, as though it automatically gets first claim on our time and energy and the rest of our lives can be arranged around whatever happens to be left.
But why are we starting there?
I would rather start by understanding what matters to someone, what kind of life they want to live, what they need financially, and what responsibilities they already have. I want to know what they enjoy, what they don't enjoy, and what their bodies can reliably support.
Then we can start looking at how the business fits into that life, instead of treating the life as something that needs to fit around the business.
And that doesn't mean the business has to be small or that you shouldn't care deeply about it.
You can be ambitious as fuck. You can love your work, enjoy spending a lot of time doing it, and genuinely want your business to occupy a huge part of your life.
I love my work. I want it in my life, and I want it to feel like something I get to do, even while recognizing that it comes with obligations and some tasks I would happily never do again.
But I also want ordinary fucking life.
I want to be home with my family. I want to have a bad day without immediately calculating its revenue impact. I want to be able to spend an afternoon doing something completely unrelated to my business without feeling like I should somehow be making that time commercially useful.
And I don't want the business to become the thing everything else in my life needs permission from.
Fantasy output is still fantasy output
You're going to get sick. Your energy is going to change. People you care about are going to need you, and there will be weeks when your ability to think, communicate, make decisions, or show up publicly looks completely different from the week before.
Some of that will be unpredictable, and some of it you probably already know about yourself.
But we keep building businesses around the assumption that we're going to operate at our best every fucking day.
We fill the calendar, create the offers, set the revenue targets, and make delivery promises based on what we think we should be capable of doing. Then the actual human being running the business has to figure out how to keep up with all of it.
And when we can't, we start criticizing ourselves.
We should have been more disciplined. We should have managed our time better. We should be more consistent. We should be grateful that we have the work in the first place.
Meanwhile, we haven't necessarily stopped to question whether what we're expecting from ourselves was reasonable to begin with.
Maybe there are decisions that need attention. Maybe commitments need changing, or the pricing, delivery, client load, and schedule no longer make sense for the business we're actually running.
I'm not suggesting that every difficult week means there's something fundamentally wrong with how the business operates.
But if we're building a business that only works when we're consistently operating at our highest capacity, I think we need to be willing to question the plan instead of constantly criticizing the person trying to execute it.
Because your life and capacity don't suddenly become relevant when something goes wrong.
They were part of the equation the entire fucking time.
And we can't keep leaving them out of our plans and then getting pissed off when they show up anyway.
Let's do the radical fucking thing
There are already enough pressures involved in running a business without making ourselves our own worst bosses.
And I think it's worth questioning how many of the expectations we have for ourselves are things we actually want, versus things we've learned we're supposed to admire.
We can care about revenue without treating it as the only meaningful measure of success. We can want growth and still question what that growth will require from us. We can appreciate the opportunities our businesses create without pretending that every part of running them feels good.
None of this means we're going to avoid difficult seasons, financial constraints, or the reality that sometimes we have to do things we would rather not do.
But I want the possibility of having a very good life to have a real place in the decisions we're making about our businesses.
And whatever that life looks like for each of us, I think we should be able to take it seriously.
Because when somebody tells me their business looks successful but doesn't feel successful, I don't want to immediately tell them to be grateful, change their mindset, or appreciate how lucky they are.
I want to know what success means to them, what the business is actually asking from them, and what might be happening between those two things.
The bookings can be real. The reputation can be real. The money can be real.
And their dissatisfaction can be real too.
So let's do the radical fucking thing and stop running ourselves into the ground.
Let's have very good lives and build businesses that fit into them.
Want to keep having conversations like this?
I spend a lot of time thinking about the decisions we make in our businesses, why we make them, and what happens when all those decisions have to work together in real life.
Sometimes that means talking about pricing, offers, capacity, or the way people make buying decisions. Other times it means questioning something we've all been taught to accept about running a business and figuring out whether it actually makes any fucking sense.
If those are the kinds of conversations you enjoy, come join my email list. I'll send you my writing, the things I'm investigating, and whatever else has me asking questions that week.