The Messy Middle: Part 1 of 2
A short series on how I’m navigating the messy middle, and how you can too.
Scroll LinkedIn for five minutes, and you’ll see two kinds of posts. Starts and finishes.
“I just started a new job!”
”I got promoted!”
”I’m starting a business!”
We love to share the start or end of a chapter. It feels natural, and people love to cheer for it. But most days, we‘re not at the beginning or the end of anything.
We’re in the messy middle.
It‘s the awkward, uncomfortable stretch that lasts way longer than we want. We have more questions than answers. Impostor syndrome shows up. We‘re not sure where we‘re going.
Maybe that’s why so few people post about it. It takes courage to admit you don‘t have it all figured out. Even fewer will admit they made a mistake or are going through a hard time.
But the messy middle isn't something to hide or feel ashamed of. It‘s where most of your life happens. And even with all the discomfort, it‘s where you grow the most.
My career
In many ways, I’m in the messy middle of my tech career. You’d think after 20 years in the industry, I’d have it figured out. But I have more questions now than ever.
Do I want to be an individual contributor or a manager?
Which path is more stable?
What do I really want to do vs. what others think I should do?
What kind of company do I actually want to work for?
Will software engineering even look the same in five years?
Do I still want to work in tech if it changes that much?
Earlier in my career, I never thought to ask these questions. Now I’m glad I do. I’m curious about them, and I’m sitting with them. I’m not rushing to answer them.
My questions about jobs have changed too. I used to ask, “Are the pay and people good?” and “Can I get hired here?” Now I ask, “Do the company’s values match mine?” and “Does the pace of the company fit my life?” These questions are harder to answer. That doesn’t make them less important.
Then there’s AI.
AI is changing how engineering teams work, fast. The job looks very different than it did five years ago. It’ll look even more different five years from now.
Tools like Copilot and Claude Code took away my favorite part of engineering: writing semantic, modular, and scalable code. I used to love writing CSS animations from scratch and building custom React hooks. Now I spend most of my time chatting with an agent. Finishing a feature doesn’t feel the same anymore. AI helps teams ship faster, but for a lot of engineers, it also takes away the part they enjoy most.
Tech has always moved fast. I’m used to learning new tools all the time. But AI has sped things up so much that keeping up feels impossible.
The good news is that what I love about the job has shifted. For the past six years, I’ve focused on leadership. Leading meetings, improving team processes, and mentoring other engineers are what I enjoy most now. As AI takes on more of the coding, people skills will matter even more.
I think those skills will help me in this new age of tech. But the question is still there.
Do I still want to work in tech if it changes that much?
My side business
I’m also in the messy middle with my side business.
I started it two and a half years ago. I’ve made a couple hundred dollars. And I still don’t really know what my business is. Not exactly the kind of thing people post on LinkedIn.
But I wouldn’t say I’ve failed. I’ve run a lot of experiments. I’ve built six apps and created half a dozen digital products. I’ve published more than fifty newsletter articles and hundreds of LinkedIn posts. I’ve hosted livestreams and had more coffee chats than I can count. And now, I’ve started coaching.
Even with all that, some days it feels like my business isn’t growing. I’ve tried a lot, but I haven’t picked a direction yet. It would be so much easier if I had a clear plan.
Right now, I don’t. And that’s the honest truth.
If any of this sounds familiar, you’re not alone. And you’re not doing it wrong.
The messy middle is full of discomfort, confusion, and growing pains. It feels messy because it is messy. And that’s okay.
Here’s what I keep reminding myself. Having more questions doesn’t mean you’re lost. It means you’re paying attention. You’re outgrowing your old answers and figuring out what you actually want.
That part is uncomfortable. It’s also where you grow.
Next time, I’ll share four things I’m doing to move through the messy middle, and how you can try them too.
What’s one question you’re sitting with right now, in your career or a side project? Share it in the comments. I read every one.