Ask HN: Founder, stressed and lacking enjoyment – advice?

[tasteful_rogue]

Hi HN,

I am the sole founder of an early stage AI/software company. I've been working on this company for 2 years and am finally starting to look for funding.

For the past couple of months I have woken up dreading my workday. I try to get myself hyped, motivated and disciplined, but I don't enjoy the day-to-day tasks I need to complete. I'm passionate about the mission of the company, and want to see it succeed, but am unhappy about how the process "feels".

I never expected it to be easy, but this degree of unhappiness is surprising to me, and I want to address it. I also find myself worrying a lot about whether or not we will "succeed" and the "success" of my career, which I believe also hurts my ability to enjoy the process itself.

Have you ever faced a period of little to no enjoyment while starting a company? What helped you get past it?

TIA, tasteful rogue

[codegeek]

"I've been working on this company for 2 years and am finally starting to look for funding."

Do you have any paying customers yet ? It seems like you are saying that you worked for 2 years before getting customers (I am assuming based on your tone) and now you are dependent on funding to move forward otherwise you are feeling burnt out ? I admire your courage so far but please tell me you have at least a few paying customers ?

Nothing makes you happier than knowing that product/idea is validated with at least few (even if handful) paying customers. If that is not the case, no wonder you are feeling what you are feeling because you are in that mode where one fine day with funding, everything will be great.

All the best. I just wanted to give it to you straight as another fellow founder. Whenever I feel down or stressed, I look at the paying customers we have and the validated product which makes me keep going even though growth sucks at times.

[tasteful_rogue]

No worries, I appreciate the straight talk!

The industry I'm in requires a ridiculous amount of pre-work before a client is willing to sign a paid contract (should've mentioned this is a B2B industry). I'm in the signing process with a client now, so will have a paying client and proper users later this year (high volume of users with this one client).

I def hear you that paying, validated customers gives direction and purpose to the whole enterprise. I'll focus on achieving that. The funding is more for the fact that I have major features that I can't implement myself while also rolling out to this customer.

[_benj]

Please take with a huge amount of salt as it a only describes my personal experience and is more of an anecdote than an advice :)

Last year I was a cofounder of an AI/software company and after a year I was starting to be burned out. I didn’t liked the people I was working with, I was believing less and less in the idea, we where running out of cash and some investors where starting to exert pressure into making the company something I didn’t really liked.

Anyway, I decided to do the math, which went something like this… in 5 years this business could “succeed” as in having x amount of users with a yearly revenue of y which could then be sold for z and with me having x percent of equity would mean that I’d make $$$. And all of that is with 12 hour days, constant pressure from customers/investors/marketing…

On the other hand, I could get a good boring job that allows me to work about 2-3 hours a day, make $, which in 5 years is similar to $$$, but I have time to live…

Well, I got the boring job (which is actually not boring! But I still work around 2-3 hours a day) and I couldn’t be happier!

I’m still working on some side projects that might have some financial potential, but those are fun again, more of an adventure than a dread.

Being in the startup game for a while made me realize that often it’s mentally is very similar to the whole idea of retirement. Work your head off, forget about happiness and fulfillment in life, break relationships, outsource kids to grandparents… and when you reach 59.5 years old and have no energy to enjoy life, maybe you’ll have money to enjoy life.

Well, screw that!! I’m living today!

[tasteful_rogue]

Interesting! One thing that stood out to me quite a bit is that you had a clear definition of what "success" means to you.

Startups can be wonderful, but only if you (I) learn to enjoy the process. I'm glad you were able to find a way to enjoy your day to day and not continually defer enjoyment to the future!

[_benj]

Thanks!

I think that at the end of the day it comes down to being raw and completely honest with oneself. Most of us have the huge privilege of having a say in where our lives are going and my fear is that we entrepreneur tend (or have?) to have some rose-color glasses and always assume that we'll be part of that 10% that makes it.

If after a naked-honest conversation with yourself starups is for you, I wish you all the success in the world and a fulfilled life!

[paulz_]

Boy I really hesitate to offer advice on this. Just know it's coming from someone who is in the midst of starting a not yet successful startup. So maybe this is terrible advice, or I may be the wrong person to give it. Seems like enough of a disclaimer.

I found myself experiencing feelings similar to what you're describing. Something that helped was not focusing on the future end state so much.

I remember one time seeing this interview with Bezos where they were congratulating him on Amazon's stock price at that time. And he was talking about how he tries to encourage Amazon employees to think in terms of inputs to Amazon, not outputs (like stock price).

I really like that idea of focusing on doing the hard work at hand and not worrying too much about what comes out on the other side.

Obviously this can go too far, you still need some vision to aim at. But I find that not only with this experience, but with learning other things too there can be sort of a stall where it feels like nothing is happening. You keep showing up every day but it feels like there are no results.

There is value in having a sort of stubbornness in the face of that. Focusing in on doing the work of the day and finding joy in it, rather than worrying about a payoff that may or may not ever come.

I think this is one of the reasons that startups work better when it's a topic you're sort of obsessed with. It helps to be able to work on something that you don't even care all that much if it leads to anything. Just a weird and interesting thread you keep pulling on.

[tasteful_rogue]

Hit me like a ton of bricks.

I've noticed within myself some long-ingrained fear of failure, and this seems to manifest as dreading my work for fear of a suboptimal "outcome" (I don't know how to solve a problem, a project takes too long, rejection/setbacks on the funding front).

Any tips or strategies that have helped you shift your mindset to being more about "inputs" other than diligent repetition/journaling?

[paulz_]

One thing that helped was acknowledging in my own mind that the worst could happen. I could fail completely. I could burn through all my money. I could let everyone down. I could embarrass myself. Whatever the worst was, I considered that could happen. Frankly it's likely to happen. Startups are hard as hell.

Then I considered I could just go back to working a normal job. Pays well, I get all my social status back. All these icky feelings go away. And I genuinely considered this. There is nothing wrong with that life. I loved those jobs!

What I found though, was that even in the face of all that risk it seemed a lot more interesting to try to do my own project.

But with those considerations I approached it a lot different. The daily risks feel like the activity more than whatever this may or may not look like in 10 years. I think this is better for the company too because it's possible to constrain yourself if you're convinced you already know what the end is like. Better to follow your own curiosity.

That's the theory anyway. Again, this is advice coming from someone who feels extremely unqualified to give it haha.

There is also a book by Carrol Dweck called 'Mindset' that speaks pretty directly to what you're asking about. You can get a pretty good idea of the concepts by googling fixed mindset vs growth mindset. The book itself has a couple slow parts but is pretty good overall.

[tasteful_rogue]

Awesome, kind of like the "negative visualization" practices the Stoics recommended, haha.

I feel like this would be a good approach for me to work on my aversion to failure.

[nonamy]

Yes, last year I had no enjoyment at all. I used to write a blog every day. One thing that put the joy out of blogging are the constant negative SEO attacks that lower the blogs google ranking I've been building over the last five years.

Sure you can disavow, but every week they add another 100+ garbage domain backlinks to your site. It gets really tiring and rankings keep lowering.

To the point where I think blogging is not a good side hustle anymore. I decided to do a lot of different things.

Think of it as just work. There's life (enjoyment) and work.

[hulug]

(Please take this with a grain of salt, seriously)

Launch as soon as you can. If you've built the MVP by yourself or with the team you've already got, don't look for funding to turn it into a more 'solid' product and just launch right now. If your product clearly solves a real problem that real people have, you shouldn't feel lost, I mean eliminating pain in people's lives is great. Also go talk to people who might be your potential users.

[jordhy]

You need to establish channels of enjoyment for your life. Sports, meditation, religion, intimate relationships, vacations, hobbies, etc. Startup life is hard and sucks most of the time for a long time. It gets easier with good people around you and money in the bank, but it's never a walk in the park.

Become resilient by building layers of enjoyment. When problems come, use these layers to dissipate pain. Hope this helps.

[helph67]

Get yourself a dog and take it to park every day, it will do good for both. Bet you both make new friends!