Midlife MavericksLast week, I got a call from a woman I’d never met. Joana found me through my column in Executiva. She’d spent years in big corporates, left a month ago, and wanted to know one thing: you’ve done this already, what would you do differently?
She asked me to be honest. So here it is.
Social media. Much earlier.
I started writing in secret. No name, no face. Deeply embarrassed, because I thought it would hurt my business. I worked with men in finance, the business grew by word of mouth, and I thought social media was for people who showed off their outfits and their lunch.
I was wrong.
Knowing how to position yourself, being able to reach people you didn’t even know existed, that’s an incredible power.
If I could go back to the start, I’d begin immediately. Even in secret. Because it’s about repetition, seeing what works, finding what you enjoy. And when you find it, going all in.
Hire help sooner
If I could go back, I’d hire help sooner.
I spent years doing things I should never have done myself. Automations, website changes, admin tasks. Every hour I spent on that was an hour I didn’t spend doing what only I can do.
Let go of the attachment to money and invest. The capacity you gain is what allows you to grow.
Those were my two direct answers to Joana’s question. But the conversation didn’t stop there.
The audit nobody wants to do
If you want to start a business, do an honest audit of what you enjoy doing and what you’re actually good at.
They can be different things. And there are things you might be brilliant at but never want to do again.
Managing people, for example. I hear this a lot from women. They can be excellent at it, but they’re already managing children, a partner, the dog, the cat, the cleaner, the whole circus. They don’t want more. And that’s fine.
The problem is that managing people is tied to status. In big companies, if you’re not a leader, it looks like you have no value. And we cling to those signals without asking: is this still important to me?
There was a time when I wanted to be a Managing Director at an investment bank. The corner office. Today I’m working with Chica, my cat, asleep next to me. I do what interests me, when it interests me, with people I admire, on my terms. Even if some of it doesn’t pay. And to get here, I had to leave some old aspirations behind.
The mouse and the lion
Entrepreneurship is a total emotional rollercoaster. You oscillate between the mouse and the lion.
The lion moments exist. Signing a new contract. Landing a big client. Getting an investment that changes the game. Publishing a piece of content that explodes and you didn’t expect it. Doing work for a client and hearing you’re the best thing that ever happened to them.
But those moments are rare. One or two days a year, if that.
Most days, you’re a little mouse and you want to hide. And you have to break rocks, chop wood, carry water, day after day, to reach those peaks. You have to be relentless on the mouse days. Keep going when nobody’s watching, when nobody’s clapping, when the only plan is to hold on.
Not everyone can do this. And there’s nothing wrong with admitting it.
Stagnating?
Joana asked: when you leave corporate, how do you make sure you don’t fall behind? Without the stimulation, the new ideas, the people pushing you.
I went quiet for a second.
I’ve learned more outside corporate than in 25 years inside it. Not double. Not triple. A multiple I can’t even quantify.
When you’re the one deciding what you need to know, learning stops being a formality. It directly affects the business, the revenue, the clients. In big companies, most of the information is noise. Meetings about yesterday’s meeting. Training sessions to tick a box.
Out here, I learned what interested me at my own pace. What I know about artificial intelligence, for example, is another planet compared to my clients.
But the isolation is real. I have days packed with meetings. Last Wednesday I had seven. Once a week, I go out for in-person meetings in London. I force myself to meet people outside my field, with completely different perspectives. We’re human. We need that.
No plan
People always ask if I always knew what I wanted, if I had a plan from the start.
No. I had no idea. Honestly, I still don’t. I’m very much a throw-it-at-the-wall kind of person.
I don’t know what I’ll write for Executiva next week. I have a workshop on Monday and I haven’t nailed down all the details. I started on Substack with no clue how it worked and within a month I had 1,400 subscribers without understanding why.
In the early years, I took on work I wouldn’t take today. Clients I wouldn’t choose. But I needed the experience, I needed to be able to say “I’ve done this before,” because having one client helps you get the next. You open up, explore, and then gradually narrow down.
Joana left a month ago and she’s already doing triathlon coaching, social organisation management, marketing and consultancy. All at the same time. She was worried she was spreading herself too thin. It’s part of the process. First you diverge, then you converge. The important thing is to never stop exploring and doing what you enjoy.
You learn these things by doing them. One day at a time. You figure it out as you go.
And of course, there will always be someone who says: “But you left that big company and now you work alone with your cat?” What other people think is their problem.
The rest builds itself. In the doing. As everything in life does.
Comment below. What would you do differently if you were starting over? I read every response.
This article was first published in Portuguese in my weekly column Oh pá, não me lixem! for Executiva.
