I’ve been working on eesel for a few years now and it’s certainly been a lot of life. I’m more fulfilled than ever, but I don’t look at startup life with the same rose tinted glasses as before and have a much more nuanced appreciation of it.
I’d always heard that “startups are hard”, but I hadn’t really grasped what “hard” meant. Well, it's an “eclectic mix of insecurities, anxieties, self doubt, unhealthy relationships with work and more” kind of hard. I thought it’d be interesting to unpack this more and how it compares to my past jobs.
The work is closer to your identity so your emotions fluctuate more
In the early stages, you're taking risk to work on something and that's usually because of some personal motivations. It could be your passion for the problem, a drive to bootstrap something on your own or something else. You’re putting yourself out there so your identity will be more attached to the work, at least by default. You have higher highs and lower lows, more often.
I’ve gone from cloudy lows of frictions with my co-founder to a high of waking up on the front page of HackerNews. Or the high of preparing for a big Product Hunt launch to a low of a really weak launch, to the high of great user feedback. All in a matter of weeks.
There are longer periods without validation and this fuels self doubt
You don't have a manager telling you that you're doing a good job. You may hit milestones as a company, but the sense of validation from these is often short-lived and you’re rarely jumping from one milestone to the next in the early days.
Here’s a snippet from my journal to demonstrate how low my self esteem has gotten at some points.
From promotions to peer reviews, you generally get recognised for hard work in a job. However, the market doesn’t care about how hard you work, and only holds you accountable for business outcomes. It can take time for outcomes to show, and worse, they’re really hard to anticipate. For instance, I spent weeks on this blog post but got no visibility, and spent 10mins on a tweet that went viral.
It’s almost all on your shoulders, so you’re in a persistent “fight or flight”
Things stop moving when you stop pushing. Things can go wrong if you stop looking. This is different to a job of course, where you’re less likely to be the bottleneck for progress.
I worked every day for 2 years straight when I first ventured into startup life. It always felt like things were at a critical point and it never felt like the “right time” to be off. It’s of course incredibly silly in hindsight, and I wasn’t exactly helping the business by burning myself out.
There are more fails than wins, so it’s easy to feel defeated
A job tends to have more structure in place which gives a good sense of where you stand, what you need to do to make meaningful progress. The path of progress in early stage life is more windy, and filled with short term failings. Some of these are part of the process of learning, and some are an oversight. It can be difficult to differentiate the two and leave you feeling like you're generally bad at all this.
For example, we’ve got a core product with healthy retention and we’ve been trying to crack team usage and product virality since. We’ve had a bunch of explorations on this path.
I’m proud of how deliberate our explorations have been and how each step incrementally builds on top of our existing system. Regardless, you can see it’s taking a few iterations and we’re still trying to find the sweet spot for virality.
There's lots of uncertainty and things to do, which can cause anxiety
From fundraising to product direction to marketing to hiring, there are infinite degrees of freedom and many more things calling for your attention in early stage life. It’s mentally draining to make sense of this open space, not be paralysed by it, find the most impactful tasks, and keep moving.
For example, as a product manager, by the time we worked backwards from our broader company strategy, what’s working well today, what other teams are up to, user feedback, and so on, there wouldn’t be much too much wiggle room for what’s next. In contrast, roadmap prioritisations in a startup can feel like an oscillation between infinite possibilities and “nothing feels like it’s worth doing”. With fewer resources and fewer facts, we’re having make tough trade offs and sweat the detail down to the week.
The work is often outside your comfort zone which hurts self esteem
You often have to pick things you have little experience with, so you'll probably not be too good to start, and this can hurt confidence.
For instance, I’ve recently had to do more marketing for eesel which is something I have no experience with, but it’s just what the business needs right now. It’s taken time to overcome my initial intimidation, up skill, and start progressing.
It’s lots of upfront risk and hard work, so you can feel stupid for choosing that
Early stage life is about investing now for outsized returns many years down the track. It's that today, especially when times are tough, the alternative feels a lot simpler and you can feel like you're complicating things for yourself. It’s pretty reasonable to question why you’re not just “working in Big Tech for a healthy base and equity”.
A stark example for me is when I catch up with old Atlassian colleagues. They’re on a clear path I didn’t take, and it can sometimes feel like I’m needlessly complicating things by choosing an alternate path.
The work can be all-consuming, so you may neglect personal things and feel guilt for that
Early stage life can, at least by default, take over a lot of mental bandwidth. You can end up prioritising work over other personal things (time with friends, family, for personal hobbies) and build guilt over this.
For instance, I missed a family Diwali dinner because we were in the middle of our fundraise, and even though it’s been more than a year - and I doubt my family cared too much (lol) - I still feel quite bad about having to make that trade off.
Everyone looks to be winning, and that can be demoralizing
Twitter is to founders what Instagram is to teens.
Every other startup is very actively talking about their wins, and while it can be inspiring on some days, it can be very deflating on most. Everyone’s “killing it" with supposedly not as much effort with their latest fundraise or "boostrapped $1M ARR in 1 week". It can be strong fuel to your imposter syndrome, and make you feel bad about your own progress.
We’ve talked a lot about the struggles here but it’s, unsurprisingly, not all doom and gloom. I absolutely love working on eesel and don’t really want to be doing anything else. It’s the most fulfilled I’ve ever been.
It simply takes time to adapt and find a sweet spot. That’s another post of it’s own but here are some things that helped:
- Find a tribe of other founders to grow with
- Build your identity around family and friends, and not just work
- Realise that you don’t “create” product market fit, and all you can expect from yourself is to explore the opportunity systematically
- Enjoy the process for today and not for tomorrow
- Get very explicit about your motivations for doing this and re-evaluate them openly
I’m by no means a master of all this (not in Nirvana just yet!) and I’m still actively trying to improve my relationship with work. I hope reading this helps others cope with their journey just a little bit better, and at the very least, feel comfort that they’re not alone in finding all this stuff super hard!
Note: The cover image was made by iterating on a generated Wombo Art