Career September 5, 2026

Before You Work for Yourself, Do the Math

Working for yourself is more work than a job, and potentially a lot more upside. Here is the arithmetic, the first customer problem, and the thing nobody tells you about how lonely it gets.

6 min read
A desk with The Art of Reinvention on an open journal, sticky notes, coffee and a Next Steps checklist

If working for the man is no longer your thing, it's worth looking at the alternative properly.

There are a lot of names for it. Self-employed. Freelance. Starting your own business. Selling art on eBay. Or the more trendy fractional CxO.

The idea underneath is the same. You sell your time, or a thing, directly to a customer.

Selling time means charging for doing something. Coaching, consulting, giving massages, driving an Uber. Either by the hour, at a fixed rate, or as a percentage of value.

The thing can be something you made, like a piece of art or a bookshelf. Or something you bought and sold for more than you paid.

Either way it's very different from a paycheck. You generate your own revenue. You find customers and convince them to pay. You handle your own taxes and paperwork. In many ways it's a lot more work.

There's also a lot more upside.

The trade you're actually making

Say you're a management consultant and your firm bills €300 an hour for your time. One month you bill 100 hours, so €30,000. You get paid €10,000. The firm keeps €20,000.

The next month you bill nothing. Vacation, or no active clients. The firm makes nothing and still pays you your €10,000.

Do the same work as a self-employed consultant and you keep all €30,000 in month one, and make nothing in month two. Over the two months you're €10,000 ahead.

You're also carrying all of the risk, and doing your own sales.

That said, you might only need one or two good customers to make a much better living than you do now. And you choose your own hours.

Over time you might hire someone to handle sales, or admin. Maybe a junior to increase your capacity. You pay them a salary, keep the difference, and now you're the firm. Ten employees later you're the CEO and barely have time to consult.

Whether that's good or bad depends entirely on you. If you're a Guide, like me, you'd probably rather keep consulting. If you're an Entrepreneur, you'd be happier building the firm.

I'm oversimplifying a lot. But it comes down to your appetite for risk, your desire for freedom, and how you want to design your life.

Building a business, even a one person business, is not for everyone. If reading this stresses you out, that's useful information. Go and get a job you actually want instead.

If you're ready to be your own boss, here's where I'd start.

Do the math

Fire up a spreadsheet if you like, but the back of a napkin is usually enough.

Write down your cost of living. Rent, food, transport, clothes, fun stuff, less fun stuff like the unexpected bills, and maybe a yearly trip somewhere warm. Let's say it comes to €5,000 a month.

Now work out how many units of whatever you're selling you need to shift to get there.

It could be a consulting hour, a piece of art, a bookshelf. Yes, different pieces sell for different prices and the carpenter makes more than bookshelves. Use an average and keep it simple.

Say your average art piece sells for €400 and costs €50 in supplies. That's €350 gross. You still have marketing, expenses, taxes and about a million other things, so knock off another €100 and call it €250 net.

You need to sell 20 a month. Roughly one a day.

Now ask yourself the actual question. Is it likely you can create and sell 20 pieces a month? Would that feel stressful or fun? Could you do 30?

If the honest answer is fewer than 20, you either reduce your living costs for a while or raise your prices. If it's 20 or more, happy days. Let's go and test it in reality.

Sell something already

If at all possible, don't leave the day job yet.

Building a business will be slower than you think, and much slower than you want. If you're aiming for 20 a month, I can almost guarantee that isn't month one. I'm rooting for you. It'll still take time, and an income extends your runway while it does.

The biggest mistake I see is people getting in their own way. It's much more fun, and much less scary, to start with the logo and the website. You can spend months preparing the perfect business without selling a single thing.

Whatever you're selling, your real challenge is finding customers and convincing them to buy. So put everything into that first.

The most successful founders I know had customers lined up before they opened the doors. Some took pre-payment.

That doesn't just generate revenue. It creates momentum. They say the hardest customer is the first one. For you it might be the first ten, or the first hundred. But once you're past it you've worked out how to sell, how to present the thing, and how to charge for it. The next one gets easier.

So find your first customer. Today.

If you're an artist, go to a local market with your existing work and put price tags on it. Or invite friends to your apartment for a pre-launch vernissage, give them the friends and family discount, and make sure you collect actual money. The confidence is worth more than the cash.

If you're a coach or consultant, activate your network. Start with people who know your work, make a discounted introductory offer, and ask whether they'd be comfortable giving you a testimonial if they get value from it. If they say no, ask who in their network needs this. If they say no to that, ask for honest feedback on your offer, your pitch and your pricing.

Whatever you're building, stop building. Start selling. You'll learn more from those first conversations than from any amount of designing.

Then deliver. Watch what they valued, what they ignored, and what they asked for that you didn't expect. Those are all signals.

Then ask your own questions. How was it? What could have been better? And the one you should never stop asking: who else should I talk to?

Charge properly

I used to have a limiting belief that I shouldn't charge for things I find easy. Somewhere I'd decided that if something came naturally and helped someone, giving it away felt generous and charging for it felt wrong.

Not a great belief for somebody trying to make a living.

My friend Valentina gave me a reframe I still use. You have to pay your bills. So you have two choices. Get a job doing something you don't love and spend your free time doing what you love for free. Or learn to charge for what you love, and spend all your time doing that.

So don't wait until you feel comfortable before charging. The first price doesn't have to be right. Pick something high enough that the customer has to make a real decision, and then let them make it.

And cheaper isn't better. Don't price from your insecurity. Price from the problem you're solving. Will your consulting save them money? Will your art make their home better to live in? Will your coaching change the direction of their life?

Then think about who can actually afford to pay, and where you can, go after them.

It's also worth playing with the model itself. Recurring revenue is interesting, because selling once and delivering repeatedly beats selling the same thing over and over. The obvious example is the lawyer on a monthly retainer. But a carpenter could supply custom furniture to a builder across a whole development. An artist could run a membership where a new piece arrives every month.

Then plan for the loneliness

This is the part nobody warns you about.

Building something is hard, especially the first time. There are highs and lows, new problems daily, and days when the beach looks a lot more appealing than the laptop.

More than anything, it gets lonely. Especially if you've come straight out of an office with colleagues and Friday drinks.

It arrives in two flavours.

When you finally win something, you might find you have nobody to celebrate with. In my old office we rang a bell when we landed a client, and my boss would email the whole team when someone did something good. I expected my first win as a coach to feel amazing. I felt almost nothing.

And when you're stuck on something, pricing or pipeline or the design limits of your Etsy store, there's nobody to complain to. I used to grab a colleague and complain over coffee, and we'd come up with five ideas by the end of it. Now I'm staring at a screen getting relentlessly positive and equally unhelpful advice from my AI assistant.

So face it early.

Work from a co-working space a couple of days a week. It'll feel less productive than your perfectly optimised home office. You might meet someone to complain to, and you might meet a customer.

Find an accountability partner, ideally someone in a similar spot. Different product, different industry, doesn't matter. Check in weekly. Share goals and progress. Help each other think.

And join or build a community. This one's my favourite. If you're an artist, find the other artists near you. Invite them for drinks. Run workshops. Put on a show where everyone gets to sell.

I did this with coaching. I'm not the first coach who struggled to find clients, and someone more experienced might get something out of how I use AI in my marketing. So we started a mastermind. Every second week, no agenda, with a chat group running in between. We share problems, we brainstorm, and mostly we cheer each other on.

On the low days I have someone to call. And when something goes well, I get the applause I apparently still need.

I'm not telling you to avoid starting a business. I'm telling you to brace yourself, because it's very different from a paycheck.

Do the math. Get that first paying customer. And surround yourself with good people.

I'm a coach, not a financial or business adviser. Anything with real money attached is worth running past someone who does this for a living.

This is the last stretch of the Embrace stage in The Five Stages of Reinvention, the framework behind my book The Art of Reinvention.

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