
Ask HN: Successful tech startup but find every day emotionally challenging - throwaway4417
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).<p>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.<p>I get home and feel like this is really difficult to keep up.<p>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.<p>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.<p>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”.<p>Is this a normal occurrence in these situations? How do I relieve the pressure?
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muzani
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.

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gdubs
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.”

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helen842000
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.

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scottshamus
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?

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contingencies
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.

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himom
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).

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martkaru
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.

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soneca
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.

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scalesolved
" 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!

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soneca
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.

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

[https://stripe.com/atlas/guides/founder-
stress](https://stripe.com/atlas/guides/founder-stress)

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amorphid
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.

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jeffrese
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.

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nickreese
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.

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rdlecler1
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.

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quickthrower2
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.

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acct1771
JIRA's not the only service with Kanban boards/carding, but agree 200%.

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joshjkim
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.

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FailMore
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!

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FailMore
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.

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jamesmcintyre
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!

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daanlo
I wrote a Mini blog post about this a few years ago:
[http://daanlo.tumblr.com/post/53208271906/had-a-tough-
year-5...](http://daanlo.tumblr.com/post/53208271906/had-a-tough-year-5-tips-
against-stressing-out-on)

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

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princeb
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!

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sp527
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.

~~~
quickthrower2
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.

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chris_wot
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.

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rookonaut
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).

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

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

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GroSacASacs
Delegate and grow

