Surviving my twenties

Fighting the quarter life crisis

Henry "Dru" Onyango
Feb 24 · 6 min read
Courtesy of Pexels

Over the last couple of days (maybe weeks, who knows?), I have been struggling with self-doubt and identity. It’s not my first time being hit with quarter life crisis, and yet knowing this doesn’t make it any easier.

Like most of my peers, I wonder if I am on the right path that was meant for me or if I am off track. I’m lucky enough to have a support system that pulls me back up, from family to friends and even my co-founders. This post however, is meant for anyone who does not have such a support system and is wondering if what they are feeling is natural.

Firstly, I think it is. I have met enough people to be convinced that what I am going through is not isolated — it’s a feeling and a phase we all go through at some point. And like my friend Given says, we live in the age of information overload and so that feeling of inadequacy and insecurity is amplified in our current generation that it previously was.

You get to a certain point where motivational videos and quotes just don’t cut it anymore. And don’t get me wrong, I have nothing against inspirational videos about living your best life or believing in yourself but what happens if it just doesn’t work anymore? Howbeit being a spiritual person, even I sometimes doubt the whole logic around the “law of attraction” and “everything happening for a reason” narrative. And this coming from someone who’s a huge fan of Master Ugwe!

After conversations with my friends and listening to a lot of Jay Shetty last night, I woke up at 4 a.m. today, took out my notebook and decided to give my self-doubt a more practical and pragmatic analysis.

You can’t beat that which you do know, right? So the first step for me was to know thy enemy. What was I really scared of? Why was I scared of it and is there anything I could do about it? I started off with the obvious one, which was entrepreneurship.


I have a couple of ventures I have co-founded and many more we are yet to bring to fruition. The notable and active one at the moment is roometo.com. Despite having thousands of users on the platform, being ranked as one of Google’s top searches and winning a couple of awards, I still questioned if entrepreneurship was really the path for me? Well, as opposed to simply saying yes and then continue struggling with all these thoughts obliterating my head, I decided to do an analysis based on Stoicism. Basically, it is imaging the best and worst outcomes and seeing if it’s something you can live with.

Ergo, here’s my breakdown on me being an entrepreneur:

What do I stand to gain (Pros)?

· Financial freedom — This was a rather obvious and cliché answer but still, I had to include it.

· Service to others — It could serve as a way for us to set our dent on the world, to build a legacy around service to others. Our platform helps makes the lives of students easier, and if we scale (and the potential is limitless), we stand to impact more lives. Beyond that, the value we create, the job opportunities that would result both directly and indirectly and the impact on the community and country in which we operate would be significant. At least to us.

· Lessons — Similar to how I had learned from our previous failed ventures, and avoided repeating those same mistakes, if this one works out (and even if it doesn’t), I stand to learn a lot which I can not only use to fuel my next venture (should I decide to pursue it)but also pass down to aspiring entrepreneurs. My skills around ideation, proof of concept, scale, team building, hiring, sales and marketing, goals and target setting, engineering, growth and so much would be refined. Already, some of those skills have been.

· A lot more time to spend doing the things I love — If it all works out, I’d spend more time doing the things I enjoy most: building more products, teaching and mentoring, playing video games and a bunch of other hobbies I’m sure I’ll pick up along the way.

Note: I haven’t included spending more time with the people I love as a pro here, because I think the pursuit of your dreams should not make you lose the connections you hold dearest. I don’t think that’s a sacrifice any of us should make.

What do I stand to lose (Cons)?

· Time — Time is the most important asset we all have. Of course pursuing something for years means putting in the time to see it succeed. If it doesn’t work out, does it mean you wasted your time? In all honesty, I don’t think so because at the end of the day, you learn a lot which you couldn’t have had you not pursued it. But then again I had to put something in this category.

· Financial losses — Part of the effort is putting in monies, save for us, very little of the cash we pump in came from our pockets. Technically, we would still be losing our money (since we got it doing other things) except we bootstrapped the venture and it pretty much runs itself. We could keep the cash. And then what? Spend it on something else?

· Embarrassment and loss of confidence — Failure takes a certain toll on you. It makes you doubt yourself and plants a seed of fear in you. People hardly ever talk about it, but failure can paralyze your growth and progress. The fear of it, and the embarrassment of repeat cripples you from taking any action forward. This is what I think i fear the most.


After doing a pros and cons analysis, I focused on the things I stand to lose and if I could survive should they occur before making a decision. And I’ll be honest with you, once I sort of “knew thy enemy” the decision becomes a no brainer. You tell me, what do you think the answer to my original question “is entrepreneurship the path for me?” is?

I did this sort of analysis with all the dreams, goals and ambitions I have to understand why I wanted them, the gains I stand to make and the risk I faced in that pursuit. It really does help narrow down the decision making process.

Before I sign off, there’s the question we all struggle with in our early and mid-twenties. It’s the thought around your destiny or your “pre-ordained” path. I honestly do not think there’s any. There’s a core value or principle in which you believe in and that’s just it. Everything else if fluid and placid. I believe our twenties are a time of dabbling and experimentation. Experimentation to unearth what those core believes are and what you stand for. If you ask me, I’d say we try as much as we possibly can before settling on one exact trajectory. The only bit we all need to learn, and this is a key reminder to myself more than anybody else, is to be patient and kind to ourselves.

As my sister always says, you doing great kiddo!!!!

Henry "Dru" Onyango

Written by

I build things that work on computers,teach, write, create solutions and lead @ http://roometo.com

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