Ask HN: Successful tech startup but find every day emotionally challenging

We are in month 20 of our busines and I’d like to think we have achieved positive things both with technology and commercially (£1m+ ARR and profitable).

I’m a software engineer and also the CEO, we have a great team (mainly all tech) and our product is great to work on and use, customers really like it.

I get home and feel like this is really difficult to keep up.

We have lots of things to do and it feels like we don’t have time to do it all which leads me to being sat here at home on the sofa in a state of questioning whether I’m over reacting at the subtle elements of start up life. I feel like “gah, what am I doing here?”. People need things from me constantly and I try get through as much as possible, delegating where I can.

I have co-founders who are amazing at their technical job but don’t seem to have that same feeling as me. They are driven but I feel like maybe they don’t drive forward or worry “in a good way” about the next thing that needs to be done to continue to grow.

I guess as I’m writing this it feels as though I’m saying: “I feel it’s all on my shoulders and it’s heavy, getting heavier by the day”.

Is this a normal occurrence in these situations? How do I relieve the pressure?

I'm not in anywhere near as stressful a situation (just a team leader), but what can help is making sure that each thing that needs to be done is in a JIRA ticket (or sticky note, or whatever you use) with a good description.

Then it has the potential to be assigned to anyone in your team: cofounder or otherwise.

It also means it is recorded, and you can have meetings to discuss priorities. Chuck it in the backlog or the "next month" bucket or get rid of it entirely, or do it right now.

Anything that slips through because you decided it was a lower priority you have to let it go. It might come back to bite you but you only have X resources.

Yes. That's what the CEO seat is like.

Everyone assumes you have the big plans, the vision, the backup plans. They are ready to follow you wherever, do as you tell them to. What they don't know is that you probably haven't figured it all out.

It sounds like what you need to do is a cultural reform. You could try delegating power to others. Delegating doesn't simply mean giving more work, it's more like feudalism where you give out more territory.

You give them the autonomy and power to do as they like. They shouldn't be asking you what to do. They should report to you what they are doing, what problems they face, whether they need more resources.

You don't give them goals. You ask them what they plan to do, and what resources they need to do it.

The long term goal for a CEO would be to completely work outside the system. You should be able to take a vacation for months without anything falling apart.

Your job would be to simply see things that nobody does. This works only when you don't have to be sucked into things. The corporation becomes a machine to be optimized. You don't fix individual habits, don't micromanage. When bad things happen, you don't blame the person, but look at a high level on how to develop a SOP to prevent this from happening in the future. Any group larger than 5 people effectively runs on habits and culture and you are the only one who can make sure the culture is right.

I am also the CEO of a tech company. The thing that I realised that chilled me out is that things don't fall apart so easily. In fact I'd say that, as long as you are a reasonably hard working individual who respects issues if they become critical, things have a tendency to be ok - even when you can see all the bits that are bad and you want to improve. So relax! It sounds like you're doing a great job. Enjoy it and try quite hard (but not too hard) and things will probably be better than ok!

Also, if my answer is useful, please look at my submissions and answer my last post - as I could use some help too. Thank you.