Notes on the messy middle

Up until the end of high school, summer always had a magical quality for me. The school year had ended, so I knew exactly what I was leaving behind. Autumn felt so far away and the time in between was filled with possibility.

I was excited about all the places I might discover, all the books I would read, all the new experiences I'd have. I never did everything I imagined I would do in that break. But the not-knowing what the summer would bring never scared me. It gave me a lovely buzzing feeling.

As I grew older, summers stopped being long and magical, simply because life stopped granting me weeks empty enough to fill with exploration and sometimes boredom.

But I found a version of that feeling again as an adult.

Whenever I left a job I took some time off, to give myself a little breathing room before jumping back into the routine of startup life. Those were some of the best gifts I ever gave myself.

I know most people don't experience the time in between things as pleasurable. And for me, too, this feeling shifted in the past couple of years. It's not hard to understand why.

When you know what you're leaving and what comes next, the time in between is a gift. You can fill it with whatever you want, however much of it you want, and you get to actually enjoy it.

But when what lies at the other end of the break is a complete unknown, fear sets in instead.

Today I want to explore that ‘messy middle’, when you’re not sure what comes next, and what I’ve learnt from others who have been through it recently.

In the last episode of my podcast, I spoke to Eleftheria about leaving the corporate world a few years ago, without a plan for what to do after. She told me:

I recognise this in many of my clients. They find themselves on the verge of leaving a company, or already in between jobs, wanting an answer for what comes next, and wanting it fast.

Most of the people I work with built their careers in tech during a time when things were easy. They moved from one good opportunity to the next, riding the wave of startup growth, never really having to stop and ask what they actually wanted. The jobs were easy to find and momentum carried them forward.

Now, in their thirties and forties, many of them are reckoning with a world of work that looks nothing like the one they grew up in. Some have fallen out of love with high-growth companies and their ways of working and some have been impacted by layoffs.

What many of them are also realising is that they never had to ask themselves what they truly wanted, because the golden cage they were in was comfortable enough that the question never came up.

For the people who were truly done with their previous work life, the phase between the old and the new feels full of possibility, the way my early summers did. They're often excited to reconnect with parts of themselves they had set aside.

For others, who were pushed out by a layoff, with no say in the timing or the ending of a comfortable and perhaps even fulfilling job, the time in between is often filled with dread. Nobody asked them if they were ready, and they find themselves in a tough place of having to rebuild.

And there are some people who feel both: the relief of leaving behind an environment that no longer fit them, and the weight of not knowing what comes next.

Imagine being a young child afraid of the dark. Your mom tucks you in, kisses you goodnight, and turns off the light as she leaves the room. You know your parents are sleeping right next door. You know the doors are locked and that the dog will start barking if so much as a bird flies too close to the house. Nothing can actually happen to you.

And yet the moment the light goes off, you start hearing sounds. Movement under the bed, whispers from the closet. Fear starts to creep in, even though nothing has changed except for the light turning off.

Being in between jobs, or two phases of life, can feel much like this. Without the daily rhythm of work, the colleagues, the small confirmations that you are good at what you do, you’re left in the dark. You lose confidence and start to wonder if everything you've built so far is gone for good.

And the future? You can't see that either. You have no idea how long this phase will last or when you'll feel like yourself again.

And in the middle of this night you start to hear things.

Comparison says: my former colleague just announced she's a VP now. We were at the same level two years ago. What exactly have I been doing with my time?

Doubt says: what if everything I’ve done in this job for the past 5 years won’t be enough to get me my next role?

Cynicism says: what's even the point of all this struggle? It’s too late to start something of my own anyway in my 30s.

Olivia, another guest on my podcast, told me that in her own in between phase, she would sit there thinking she should be doing something, but not knowing what. Some days, she said, it was hard to even get out of bed.

And there’s absolutely nothing wrong in sitting with these feelings for a while and mourning for a part of your professional identity that you’ve lost. But if you’re anything like me, sooner rather than later you’ll want to find your way towards the light.

What follows isn't a checklist, but a short collection of suggestions shared by people who have navigated the in between phase recently and who found these simple things helpful.

Here’s how Olivia put it:

Especially if you’re low on energy, start by making small changes. Switch up your routine, try a new workout, read a book you never thought you’d read.

Anything that shakes loose some new energy, helps remind your nervous system that movement is still possible.

Approach this phase with curiosity. You start to see light at the end of the tunnel the moment you feel a flicker of excitement again, so let yourself follow it.

Notice what kind of content you keep coming back to, and what you like about it. See what catches your attention when you're on holiday, or wandering through a new part of the city. Or is there a problem that you’d like to solve and can’t stop thinking about?

The more you follow what interests you, the more ideas you'll have. And the more ideas you have, the more options open up.

In our conversation a few weeks ago, Eleftheria recalled the time when she was on sabbatical in Greece, when she already knew it was time for her to leave her corporate role. She said to me: “I remember visiting a store that had a collection of wines and honeys and other products made on the island, and I instantly felt like I want to have a store like this”.

This was the moment when she started to see the light. One year later, she’s growing her olive oil business from the Netherlands, all because she let herself be guided by curiosity.

Whatever you do, don't get stuck in your own head, and don't spend your evenings burning tokens with Claude instead of talking to a real person.

You need other people: to bounce ideas off, to get inspired by, to learn from. In a world where social media pushes us toward comparison and AI chatbots offer the illusion of having all the answers, it's easy to slide into a kind of social apathy. But we are wired for human connection.

Find people with common interests and do things together. Go to a meetup. Find people two or three steps ahead of you on the path you're considering, and ask them out for coffee, just to learn from them. You'll likely hear that they went through their own uncomfortable in between, too, and came out the other side.

If you're in Berlin, I have an invitation for you. I host a walk across Tempelhofer Feld for people who are working in tech or VC and are starting to think about exploring a new direction. It’s a chance to meet other people who are thinking about similar things, and to start to say out loud what life after tech might look like.

We are meeting again on the 7th of July, and you can register here.

Try things out

I keep coming back to the Tiny Experiments framework of Anne-Laure Le Cunff, because it's such a playful, low-pressure way to explore.

Here’s how it works: you pick something you want to try, you commit to it for a short, defined timeframe, and then you look honestly at what happened. Did you do it? If not, why not? Do you want to try a different way of doing it next time? If you did, what made it possible for you to do it? What did you enjoy? When you use this experimentation framework, you're not committing to a new life, you're just gathering data and testing things out.

I’m trying it myself right now, to see whether having a podcast is something I want to go full in on. For now, I committed to releasing one podcast episode a month for five months. I released three already and I’m learning a lot about the process. I still haven’t decided what happens after episode 5, but my data will tell. You can listen to them here. If you do, I’d love to know what you thought.

So if you have a career path or project in mind that you’re looking to explore, give it a try. Say I will do x, for y amount of time. And see what happens!

These in between moments can be filled with possibility, if you give them a chance.

So, what will you do this summer? Will you let me know when you’ve found that light switch?

If you're ready to move from thinking about change to actually making it happen, I work with clients over three months through the pillars of clarity, curiosity, and courage. We build a roadmap together that turns your intentions into momentum. If you'd like to explore working together, schedule a free discovery call.