The questions and challenges only other midlife founders will understand

There is the questions we ask openly. They are about...

Leads. Sales. Content. Pricing. How to organize the week.

Then there is the one that get into our heads when nobody is around.

Today's newsletter is about those questions of self-doubt and worthiness.

How did I run a team and now struggle to prioritize my own work?

You used to walk into a room, understand what mattered and help everyone else focus.

Now everything feels important and you have no idea where to start.

Should I... Work on sales and you worry about delivery. Work on delivery and you worry about having no pipeline. Write content and wonder whether you should be talking to customers instead.

Then the day is gone. You were busy. You worked hard.

And it still does not feel like you made any meaningful progress. 

Then that ugly little question shows up.

Did I lose it? Have I ever had it? Was I only good at this because I had a team and a company around me?

Why does writing like a normal person suddenly feel unprofessional?

You write something that actually sounds like you. Then you read it back.

Too simple. Too casual. Someone with my experience definitely needs to sound smarter than this.

So you add more words. Make it more professional. Remove the parts that feel too personal.

Now it sounds like every corporate post you never wanted to read.

Deleted.

Try again tomorrow.

Why does selling my own work feel salesy as hell?

You know you need clients.

You also do not want to become one of those people sending salesy messages, manufacturing urgency and turning every conversation into a pitch.

So you hold back.

• You explain what you do, but never really make an offer. 
• You send the proposal and feel weird following up.
• You try to sound relaxed when you are absolutely not relaxed.

Then nothing happens.

I want to be respectful. Maybe I am just afraid to hear a no.

Hard to tell sometimes.

What are my former colleagues gonna say?

You publish something and immediately imagine them reading it.

Who does he think he is now? I don't get why he left for that? Have I lost my respect?

They remember your old title. The work you did before. The person you were inside that company.

Some might actually support you. What if they think I am having some kind of midlife crisis (Damn. Do I?). Should I be happy if they don't care at all?

You have no idea. And not knowing is killing you internally. 

Why does it feel personal when I cannot put my best work into everything I do?

Your best work was part of your identity. Still is. To some extent. 

You were the person people trusted because you cared about the details and refused to put your name on something mediocre.

Now there is too much on your plate. 

The website could be better. The content could be better. The offer could be better. The client work could always be better.

You know... You cannot give everything your best because there is only one of you.

And still, it feels like you are lowering your standards.

What if I am actually successful at this? And what if I am not?

Failure is scary for obvious reasons.

You left the job. Told people what you were building. Put your name on it.

Then the doubts start... 

• What if nobody wants it?
• What if you have to explain that it did not work?

On the flip side, success can be scary too.

More clients. More pressure. More people depending on you. 

My calendar already is full. How am I gonna take on more?

What if I build something successful and hate running it?

Both outcomes can scare you enough to stay somewhere in the middle.

I wanted freedom. Why does it feel so freakin scary now?

Nobody tells you what to do anymore. That was the dream.

Until it wasn't anymore...?

Then Monday morning comes and there is no clear plan what matters this week.

There is no salary arriving because you showed up. No boss carrying the final responsibility. No safety net if something does not work.

Every decision is yours. So is every result.

On some days that feels incredible. Most of the days you would really want someone to tell you what the hell to do next.

Who am I gonna ask when I get stuck?

There used to be someone.

A manager. A colleague. Another team. Someone who knew the context and could help you think.

Now who do I ask?

Your partner cares, but they are not inside the business. Your friends think you are brave, which is nice but not especially useful. LinkedIn has plenty of opinions from people who do not know you.

AI will confidently give you seventeen possible answers. None of them can tell you whether you are making a smart decision or hiding from the uncomfortable one.

Sometimes you do not need more information. You need someone who actually gets it.

Have I made a mistake leaving corporate?

This question usually shows up on the bad days.

Corporate suddenly looks a lot better than it felt while you were there.

The salary was reliable. People understood what you did. You had a title, a team and a clear place in the world.

Maybe I should have stayed.

Maybe leaving was the stupidest thing I ever did.

Am I too old to start again?

So you ask. Should I go back before the gap gets any bigger and everyone realizes this did not work?

You remember why you left. But fear has a funny way of rewriting your old story.

These thoughts get louder when you carry them alone.

You need people who can hear one of these questions and say:

“Yeah. I hear you. I have been there too.”

People who understand why a quiet week can shake your whole identity. Why freedom can feel terrifying. Why someone with twenty years of experience can feel completely lost on a Tuesday afternoon. And why advice from a 30-something doesn't help. 

People who can help you work out whether you have a real business problem or you are deep inside your own head again.

Who can remind you why you started. Call you out when you are hiding. Share what worked for them without pretending it has to work exactly the same way for you.

Building a company alone is hard enough.

That's why I am building this community, and I am glad you are here.