At a very young age, I discovered one fundamental truth about myself: I don't settle. Once I set a goal, achieving it stops feeling like an option and starts feeling like an obligation. I have to get there—whatever "there" happens to be. Healthy? Debatable. But it is something I've come to accept about myself.
Over time, I've realised that refusing to settle comes with a sacrifice. If I wanted to keep reaching for bigger things, I had to let go of the idea that failure was something bad. I had to stop treating failure as the opposite of success and start seeing it as part of the price you pay for chasing something that actually matters.
Learning to see failure as a means to an end has required me to let go of a lot of pride. It has forced me to become comfortable with getting things wrong, being rejected, starting over, and sometimes looking like I have absolutely no idea what I'm doing—which, to be fair, probably happens more often than I'd like to admit. But accepting failure has also brought something else with it: a lot of self-doubt.
Because the truth is, my work matters deeply to me. Just below my relationships with my family and friends, I value my career and the life I'm trying to build for myself over the next ten years. I think about that future constantly. I think about the person I want to become, the things I want to create, the rooms I want to be in, and the kind of life I want to eventually look around at and say, Yeah, I built this. No pressure whatsoever.
And when you care about something that much, failure becomes complicated.
At 22, I've already taken more risks than I sometimes know what to do with. Some have cost me money. Others have made me money. Some have completely changed the direction of my life. I have three failed marketing agency ventures under my belt, two degrees that have almost nothing to do with my current career path, a hobby that somehow became a passion, and a career that I question at almost every step of the way.
Three Agencies and a Dream
In 2022, I started CTRL Marketing. CTRL Marketing became Be Social, and Be Social eventually became GoodRoots Marketing. If nothing else, I am apparently very committed to rebranding.
Somewhere along the way, I managed to make more than $1 million in profit and, unfortunately, also managed to recklessly spend all of it. That is an achievement in its own right, and probably deserves an entirely separate confession.
On paper, you could probably call the business a success. I built something. People trusted me with their brands. People paid me. The business made money. And yet, none of those versions of the agency clicked enough for me to truly follow through with them.
Eventually, I moved on. Three times.
Maybe that says something about my ability to commit. Maybe I get bored too easily. Maybe I'm addicted to starting things. Or maybe I've spent so much of my life chasing the next version of myself that I haven't always known how to recognise when something in front of me is worth staying for. I'm still trying to figure that one out.
So, Obviously, I Started Another Business
After all of those abandoned ventures that I have absolutely no plans of returning to, I decided that the sensible thing to do was start another one—and this time, I did it publicly, because apparently failing privately wasn't stressful enough.
I launched Clippy, a software platform I am incredibly proud of, with the enthusiasm of a kid opening presents on Christmas morning. I was obsessed with the idea. I was excited about what it could become, excited about building something outside of what I had already done, and excited enough to tell people about it before I had the chance to quietly talk myself out of the entire thing.
Then came the fear.
The moment I started putting Clippy in front of other people, I became painfully aware of my track record. Three attempts at building an agency. Three times I moved on. Need I say more?
Suddenly, I wasn't thinking only about the product anymore. I was thinking about perception. What would people think if this didn't work? Would they look at Clippy and think, Here he goes again? Would they assume it was another thing I would get excited about, post online, obsess over, and eventually abandon? Would they think I wasn't serious?
Worse, would they think I was a failure?
I was scared, and if I'm being completely transparent, I was a little embarrassed too. Not because I thought Clippy was a bad idea. Quite the opposite. I believed in it enough that the possibility of it failing scared me even more.
By announcing it publicly, I was giving people something I had spent years trying to avoid giving them: a front-row seat. They could watch me try, which also meant they could watch me fail. That terrified me.
Maybe I Am Afraid of Failure
For someone who claims not to be afraid of failure, I eventually realised something slightly inconvenient: I am incredibly afraid of being perceived as one.
There is a difference.
I can handle an idea failing. I can handle changing direction. I can handle losing money—clearly. I can handle starting over. What I struggle with is the thought that someone might look at all of those things and decide that I am the failure.
Logically, I know that shouldn't matter. Most people are far too busy dealing with their own lives to maintain a detailed spreadsheet of my failed business ventures. At least, I hope they are.
But ambition has a strange way of making everything feel public. Every success feels like proof that you're becoming the person you said you would become, while every failure can feel like evidence that maybe you aren't. Somewhere between those two extremes, you're supposed to build a life and somehow remain sane.
So, What's the Conclusion?
I honestly don't know, and I think I'm okay with that. This is a confession, not a TED Talk.
I don't think I'll ever completely get over the fear of being perceived as a failure. Maybe that fear will always exist somewhere in the background every time I announce something new, change direction, apply for something I'm underqualified for, put another idea into the world, or decide—against all available evidence—that starting another company is a fantastic idea.
But I also don't think I'll ever let that fear stop me from creating, taking risks, trying something, getting it wrong, learning from it, and starting again. Maybe being unafraid of failure doesn't mean feeling nothing when things fall apart. Maybe it doesn't mean becoming so enlightened that rejection suddenly feels wonderful and losing money becomes a fun little character-building exercise.
Maybe it simply means deciding that the possibility of failure is not enough to keep you from starting.
Because the truth is, I'm still terrified of people watching me fail. I'm just more terrified of looking back one day and realising I was too afraid to try.