So I’m starting over

Reflections and motions after a year of entrepreneurship.

Last week, I left my engineering job at an AI startup and quit a software agency side hustle to now start from zero.

I had spent the earlier half of last year with my first ever break into entrepreneurship with an AI tool called Dory AI. We experienced some small successes with user sign ups and paying users, but ultimately we decided not to continue. Looking back, I felt like we didn’t have the grit back then to do what it takes to make it work.

My co-founder got an internship and I started looking for a job and landed a role at a pretty notable Australian AI startup, Relevance AI. A few months in, I tried making money doing freelance software and AI projects, and a while after that tried collaborating with two other agency founders to build a new agency. That didn’t turn out well and I recently left that business as well.

So the general feeling is starting over. I’d say I’m feeling excited and nervous. I’ve made decisions that bought me freedom and creativity but at the cost of stability and certainty. I’m still in university so some might say the stakes aren’t entirely high — I could even take the next few years doing nothing and no one would blame me.

But these experiences in the past year have really taught me more about what it is that I want out of this life. The difficult experiences have made me more honest about where I’m at and what it truly takes to build something worth while.

Now that the dust has settled in a bit in my life and a new routine has formed, I’m writing this as a reflection on what’s happened and where things are going from here.

What did I learn

Emotions. Egotism, envy, doubt, anxiety. The truth is I wasn’t prepared to see how these emotions would affect my character and my progress in life. Arrogance and jealousy are a huge blocker to focus. Doubt and anxiety can crush creative thinking and optimism. Both which I’ve come to prioritize and protect more recently now. I try not to beat myself up from having gone through these, and instead think of the hero’s journey: it’s true that experiencing these emotional hurdles were difficult but ultimately have made me more resilient for the entrepreneurial path ahead. In order other words, this was necessary.

Risk and reward. A job is low risk and stable; you can climb the ladder to make incremental improvements in your salary and the reward is predictable. Freelancing and consulting has a similar feeling the more projects I did: I’d slowly build up skill to be able to charge more and complete projects faster, but ultimately I was trading my time for money. I do think it’s a good place to start a hustle especially if you’ve built up a lot of experience. But building something that lives outside of your time is truly scalable. The risk of it not working is high, but the reward is as well.

Personal life. I spent a lot of time last year being “busy” but ultimately I felt like I didn’t achieve huge amounts of success. I’d also neglected relationships with partner, friends, and family, and potential new ones as well. I look back and feel like I had fewer memories than I wish I did. I spent a lot of time trying to just be a mode of working but ultimately was “fake” working. I had less clarity on deciding on the things that mattered and justified the grind as a way to amass respect from others, but in a way to myself, telling myself I was doing the right thing to become successful. I’m starting to question this a lot more this year.

What will I do

The mind is the real startup I’m building, a version of myself that continually seeks learning, challenge, and growth. The negative emotions and bad times are unavoidable, but they are necessary to continue to find meaning and drive in what I do. To find what really gets me up every day. It’s the trials and tribulations every day that I believe will contribute not only to a successful career but a successful life. I’m spending mornings now exercising and in deep work. Planning my day the night before, and being more intentional with creating space for reflection, learning, and creativity, usually in the afternoon.

I’ve said no to many things: not continuing my job, not dropping out of university, not doing the new agency business. And yes to many things that I wouldn’t have before: having friends over for dinner, afternoons for thinking and wandering, meeting new people and trying new businesses. I’m building SaaS products again: an old project called NemoAI I worked on last year and one for a client. As well as exploring AI agents, image/video generation, and education/community businesses. High risk, high reward is the plan.

I’m trying to unlearn how a successful life should be lived. Can I be rich and have a personal life? Do I need to spend excessive hours on something during my 20s to make my 30s free? Is working a few hours focused better than many distracted? To take my time to deliberate but ultimately being more decisive and protective of my time and energy, and channeling that into things I believe will be worthwhile, not just in business but in relationships and experiences.

Conclusion

I have nothing to show for yet but I’m building it. Quite frankly right now I don’t even know what that is. But I think about the end of history illusion a lot: we usually know we’ve changed a lot in the past but think things will be the same in the future. Trusting that this year will be that of growth if I’m intentional with it consistently. See you on the other side. And thanks for reading.