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

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.

A lot of leaders in high stress situations, from Phil Jackson to Ray Dalio incorporate some form of mindfulness into their lives. It can even be going for a run, and really just focusing on that and nothing else for fifteen minutes.

Giving the executive areas of the brain (the prefrontal cortex) a rest is important. It can even be a few minutes in nature, a walk, etc. I prefer meditating, but it’s really just about calming your conscious mind for a bit, focusing on your breathing, being in the moment.

I’m reading “Incognito” right now. It’s about contemporary neuroscience. It’s amazing how much our unconscious mind plays a role in finding insight and making decisions. We have a tendency to want to consciously figure everything out. Sometimes letting go can be incredibly productive. Think hard about a problem, then let it go. Meditation can make it easier to do that.

Phil Knight, founder of Nike, said in his book, “Shoe Dog”, that “if all you’re seeing is problems, you’re not thinking clearly.”

If you sit quietly and think for a few minutes, where is the pressure coming from?

Is it the constant demands from colleagues? Is it the responsibility? Is it coming from yourself?

Figuring out what sits uneasy with you will give you a starting point to take action.

Learning to listen to your gut and then using it to produce a positive change, but not just for you - for your whole team.

The good thing here is that you're the CEO and that means you are in control.

You've gone through nearly the first 2 years on adrenaline, hard work and probably a good dose of hype. That is probably wearing off now as you transition into the next stage. That means you need the room to take a breath. Your team won't say it but they probably need it too.

You have probably put a lot of things on the back-burner while you were getting started.

For sustained success you need to re-prioritise mental and physical health above all else.

For this to be sustainable, it's time to optimise for happiness.

Depends on what you are worrying about. Is it your product's future? Competitors? Keeping customers? Managing employees' performance? In my experience, stress comes from having all of these problems but not having any plan. I would write out everything that is stressing you out then try to find the highest priority. That feeling of having too much to do is a GOOD thing. It means you have tons of ideas or your customers love your product and want to improve it. That should never go away if you do your job correctly. You just need to develop strategies to know when your roadmap is full and how to manage scope/expectations. Maybe you need a Product Manager or Salesperson to handle expectations from your customers?

Month 20 and £1m+ ARR? That's absolutely fantastic!

Project the growth, maintain the metrics, court the PE dealmakers, sell the business and get the hell out of there. You deserve it.

Nothing is worth your health.

Delegation. Hobbies. Exercise. Fitness. Partying or similar. Travel.

Above all.. teach others to work themselves out of a job and gradually do it yourself.

Work is great, in limited amounts. Killing yourself doesn’t win any rewards. Delegate, delegate, delegate (wisely, of course).

Ignore the vacation, hobbies and meditation nonsense mentioned here. You need to attack the core of your problems.

You need to delegate, but before that, I think you need to think through your company's structure and have a clear separation of roles and responsibilities. You are saying you are the ceo but also do engineering in a ~20 person mostly dev-oriented team, that all might point to badly defined roles/responsibilities.

There are classically 5 roles in every company (some companies might have less, some more) - 1. the visionary (the person who has the crazy ideas and looks more into the future) 2. the integrator (CEO) 3. head of operations (the product/service you are developing and/or running) 4. head of admin/finance 5. head of sales/marketing

Each of those roles should be filled with one person. That person is also the single one to be responsible for performing in that role in that area. All the other roles should not micromanage the other role's responsibility areas. The role of the ceo is to work on the company systems and see that all of the "heads" are ticking ok (kpi-s are met, tasks have been done, etc) and communication is in place. Smaller companies can also assign multiple roles to a single person.

If that kind of structure is in place, it is much easier to delegate.

I am not in that position, but I have a few friends that are. My advice would for you to hire a COO - I say hire instead of promoting because I am assuming that if there were someone with the skills for the job you would already have noticed and not be feeling that much pressure.

A non-technical COO can be helpful to discuss the vision of the company and share the responsibility to execute it.

A friend of mine is Co-CEO with 2 others. It works great for them (but they know each other for some time). The key is that anyone of them can make most decisions without consulting the others.

" I say hire instead of promoting because I am assuming that if there were someone with the skills for the job you would already have noticed "

Whilst this could be true there also is the possibility for the OP that the business has grown rapidly and they are still trying to operate the same way as the early months, trying to be involved in too much and not delegating control and decisions.

My advice would be to have an honest conversation with the whole team, show the trust to be vulnerable and I'm sure if the team are great as you say people will find a way to pull together.

If these things don't work though as another poster mentioned, sell the business and protect your health. Best of luck!

You are right, I jumped some steps. I wholeheartedly agree that the first step is to be transparent with the whole team and tell them the situation. Ideally with all the team, but if there is not so much trust with everyone, at least with the co-founders and all the most senior and team leaders employees.

There is a great article on this, hope it helps.

https://stripe.com/atlas/guides/founder-stress

You just described my experience as a first-time CEO/founder.

One thing that helped me was getting better at expressing things in terms of what I needed & why I needed them. It was extra important to make sure the person(s) with whom I spoke understood by explaining my request back to me. I didn't always get the exact results I expected, but I usually got what I needed, or an understanding that a different might be in needed. It also helped to only request things that I really needed.

Meditate each morning and afternoon. That will help an immeasurable amount. Headspace is a good app for that but I prefer TM. Also, take a hit or two of weed then netflix and chill. The weed won't give you a hangover like booze does and you'll be super productive with energy the next morning after you meditate.

Your story is one I identify with 100% as of this writing. Differing circumstances but same core feelings.

Best way I can describe it is a mix of decision fatigue (all the problems roll up to a decision maker) and a need to feel like you’ve got the future figured out because those around you expect you to have it figured out.

Have you talked about it with your partners/investors? For me, the most powerful shift and action I’m taking is to chunck down our general direction for the next 2 years into specific tangible goals. It doesn’t really relieve the pressure but these goals give you an actionable framework to talk with the people you need support from to make them happen.

The talking and getting other people stoked about the future is what is helping to relieve the pressure in my situation.

Ping me if you want to chat.

What helped me was to start saying no to a lot of things so that you can primarily focus on what matters. Put an ROI and place a dollar value on your time to help you make decisions about how you allocate it. A partner at a law firm might bill $1000/hour so that may be a good place to start. As the CEO you’re the pace car. You can’t expect people to work harder than you and that’s a challenge because you may be working with multiple teams, each one of them involved in a sprint at some point, but you don’t get that luxury. It’s tough but hopefully with some scale you can get more support on the things you’re less good at or don’t enjoy.

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.

JIRA's not the only service with Kanban boards/carding, but agree 200%.

it's normal and you can expect that no matter what, as CEO you'll have phases like this on/off throughout your tenure, for better/worse it is part of the job. that being said, without knowing more details, I'd venture a guess that after 2 years, you are at a size (in terms of customers, volume, team size, etc.) where you may need to start thinking about not just getting shit done, but managing your team more actively (the thing that clued me in on this beside time/revenue is "people need things from me constantly"). there's lot of resources for how best to do this, but overall it all comes down to identifying big picture goals for the business, setting clear direction for your team, identifying metrics for performance, and then allowing your people to operate relatively autonomously but have regular check-ins / reports on performance relative to the established metrics. this can be as simple as well-defined product development milestones, support tickets closed, sales number achieved, customer acquisition targets, etc. it's important to identify the correct metrics, but often times part of that process is just starting with something simple/obvious, being consistent in evaluating, and then being willing to adapt / add / modify as you and the team learn what really matters.

hope this helps, doing similar things at my company now, not easy but once I appreciated it as a new problem set it's been interesting and satisfying to work on. hit me up if you want to chat more, happy to help.

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.

I think a leader displaying calmness, confidence and even a sort of levity towards imposing problems or struggles is very valuable even if this may be a practiced behavior or a kind of "performance" (if only in the beginning). In other words, maybe what's most valuable at any given moment is not to have all the answers for everyone in every situation but to exude an attitude which suggests "this too shall pass" and "together we'll figure it out". Over the long-haul it is likely more impactful to foster this environment and to calm those around you so that creative solutions have space to emerge instead of stirring anxiety and fear which may in turn be a hostile environment for collaboration and creativity.

I know this sounds a little idyllic or lofty and you may be thinking "yea except every day there's a problem that could actually kill our startup so I can't just act like everything's ok all the time" and this is where your role becomes uniquely challenging in that every day the sky may actually be falling, you aren't just imagining it- so how can you keep your cool?

I don't claim to know the answer but I have a feeling it involves striking a balance somewhere between being passionate, being personally invested and seeing the startup as a reflection of yourself and then on the other end centering yourself in a place of "detachment from the outcome", reminding yourself that you'll live and that "this is all just information".

I can't say I know fully how to strike that balance but this is the approach I shoot for. I think there's real power in detaching from the outcome of any given arbitrary situation- this gives space for creative solutions, rich contributions and better energy. This doesn't mean you don't care about the "success" of the startup, you can care deeply; it means you do not fear the land mines, the possible missteps because you know that these seemingly scary foes are actually bits of information, encoded information or even opportunities and that you and your team will be wise enough to see them as such and react appropriately where other's may let fear take hold and be blinded.

A book comes to mind, if you haven't already you should check it out: Antifragile by Nassim Nicholas Taleb.

Hope this helps! Remember... you got this!

I wrote a Mini blog post about this a few years ago: http://daanlo.tumblr.com/post/53208271906/had-a-tough-year-5...

In General: what you are Feeling ist absolutely normal. It will get easier

you will never feel like you will run out of things to improve on. you will never feel like it's a complete work.

what is worse is knowing that there are competitors and they are also trying to find their edge over you. you have probably between 20 to 50 different things you can choose to work on right away and there's always this nagging doubt that the projects and improvements you pick may cost you far too much and give you back far too little.

it always does feel like a hair's breadth away from failure.

i don't know how to help you. you may have great, productive employees who are 100% willing to jump off the cliff with you but at some point you will need a few good, smart, strategic guys you can bounce ideas off, who can critique, find flaws, figure out escape plans when things don't go right, and give you confidence to take on projects that may not be in your favour.

there's no formula to finding those guys. it's a tough battle. good luck!

It seems like the easiest way to relieve the pressure would be to hire someone to take over as CEO. Finding the right person may be hard, but you'd probably feel a lot better once you've been swapped out. You would likely want to remain in charge of product and hand off the rest of the business decisions to said person.

That's a bit like hiring someone to manage your money. Delegation not abdication. I.e. you can't sit back, relax, you need to keep an eye on their performance and how they act and behave and make sure it is in line with the company goals.

It sounds like you are about to burn out. You need to take a holiday. And I'm quite serious - I burned out, and if I'd taken a holiday I suspect 3 years ago my life might have been quite a bit better than it is now.

I have been in the exact same position as you are. If you want to share experiences and learnings or simply talk about stuff, feel free to get in touch with me (mail in hn profile).

Get someone to help you manage the CEO tasks. Maybe what you really enjoy doing are the technical aspects?

How do you know that you are the only one feeling this way?

Delegate and grow