As the old guy at a start up

Posted by on 9 November 2022

I’m 15-20 years older than most of my colleagues. I’ve done a couple startup things in previous eras, but not a modern venture backed startup. I knew mostly what I was getting into as I was actively seeking it out. There’s no critique here, these are just a collection of findings from my first few months that many old and young will relate to.

“An old wizard from fantasy fiction trying to order a latte at starbucks, impressionist style” - DALL-E 2
“An old wizard from fantasy fiction trying to order a latte at starbucks, impressionist style” - DALL-E 2

Mental Health is Taken Seriously

Mental health is a major concern in the tech scene and a recent post of mine about acute mental health issues camped out at the top of HackerNews for a while. In the comments were countless stories of breakdowns, suicide attempts, mourning and a general state of mental unhealth.

Talk to anyone in software or technology who’s in their 40s and they just got back from leave, they’re on leave, about to go on leave or they just quit their job and are laying low. They’ve burned out. The path to remaining in technology by your 40s was risky one, where you lived at a breaking point continually without any help and no template for even discussing mental well being. Nobody was watching out for us. Everyone just piled on. Nobody asked us how we were doing. Not ever. Until now.

I’m so impressed right now. This is being taken seriously. This new generation is on it. Everyone is talking openly. Their trauma is known and well documented. Help is there, techniques and models of mental well-being are studied and frequent check-ins are are keeping it top of mind.

This is the way and it’s long overdue.

Imposter Syndrome

I find this one almost adorable. Nearly all of my colleagues suffer from a serious case of imposter syndrome. They’re moments away from being found out. Someone is going to confront them, ‘AHA! I KNEW IT! YOU DON’T KNOW WHAT YOU’RE DOING!’ Guess what? I’m still waiting for that too.

I tend to rely heavily on pattern recognition and learned shortcuts. If you’re earlier in your career, you don’t have as big a dataset to draw on those patterns and devise shortcuts. But here’s what I’ve learned about my colleagues. They sure as hell can use first principle thinking to work towards solutions. Breaking things down to their component parts, understanding problems and remixing into new solutions is a definite strength. Put another checkmark in the impressed column.

One thing that I try to remind everyone who suffers from imposter syndrome is that, for your role, in your product category, you’re one of the few experts in the world. You do know best. You’re an expert in this specific thing. This applies to almost all roles. Let’s say you’re hired as a Associate Product Manager for a digital signature platform. By the time you’re done orientation, you’re already more expert than most of the world. After a year, you’re in an elite category of experts on that market and product space. Embrace it and remember it when doubt sets in.

Not Yet Broken

I’m a little broken. I’m skeptical. I don’t care about the latest buzzwords. I don’t care about the hot new methodology. I don’t care about the latest business book and the groundbreaking framework. Show me your revenue chart and all the ways the buzzwords influenced it. Show me how your buzzwords retained your team and let you spend time with your family instead of working every night and weekends.

I’m broken in so many ways. Partly because of years of internal politicking, managing up, being thrown under the bus, seeing sales quotas pulled out of thin air, finding release dates magically changed in board decks, grinding on RFPs to find out they’re rigged or solving the same problem a dozen times.

My colleagues aren’t yet broken and it’s rubbing off. Work is exciting again. It’s still hard as hell, but all the problems seem solvable. The world of software development is still just as broken as me, but the next roadblock doesn’t seem like as big as a slog since we have only momentum at this stage. Inertia isn’t in our vocabulary.

My Emoji Game is Weak


Listen, I came up through the entire evolution of emojis. From emoticons, fucking wingdings, all the way up to unicode. For me, emojis were something used in private speak, over sms with friends or in chat rooms online. You would never use them in corporate communication, or in marketing copy. Things have changed and it’s pretty cool. My colleague’s emoji game? 💪.

Content Sprawl

When everyone is empowered to just get shit done, you end up with content sprawl. Grab the tool that’s easiest for you in that moment of go for it. This is an absolute blessing when you’re a small team. As a new hire though, it makes it hard to find the source of truth, because there often isn’t one.

My philosophy on this — if there isn’t a source of truth, the content isn’t likely important enough to hold on to. I’ve found lists of product ideas in Notion, Jira, Asana, Airtable, Google Docs, and Miro. Some overlap, some don’t. If you start at a new job and find something resembling a backlog in many areas, for your own sanity, thrown 90% of this out. It’s most likely a good idea to throw anything out that hasn’t been updated in a couple months. In start-up time, after a couple months it’s old news and no longer relevant. Don’t treat it as precious. Good ideas will return if they’re good.

The content sprawl was created in the name of efficiency, but the reason you documented it was so that you could easily leverage it later. That is, if you can find it. Sprawling content leads to re-inventing the wheel several times over. I swear we listed out our beta launch plan somewhere? Oh well, I’ll just restart it over here. As your team grows you definitely want to centralize knowledge, and avoid wasteful cycles searching for and re-creating content.


I’m only 4 months in. We’re in the middle of a pretty hard pivot in product direction, but the core market thesis remains the same. Similar to my career, it feels like a Re-MVP, where we adhere to the same vision, just a new approach on a new tech stack. The whole team is fantastic, excited to embrace change and looking out for each other. We’re at the start of a fantastic ride. 📈

Published April 23, 2022


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