A never ending want to start over.

I have been creating content brands ever since I was 16, I have this odd passion for building small digital assets about the things I love, this could be about retro games, camper vans, consumer tech or electric vehicles, the list could go on forever.

Most of them, if not 99% of them have failed miserably, but a couple of them have worked out incredibly well.

The largest being Retro Dodo, a project I have loved building over the last four years, and it has taught me a lot about growing digital assets and how community is important when building brands.

Retro Dodo is getting to a size that certainly tests me, it pushes me to learn more, and has forced my hand to think like a businessman instead of a content creator.

Every month that the asset grows, an uncontrollable, strong conscious thought penetrates my mind on a daily basis, it makes me think about what I truly want to do, and how a potential sell could create a new new branch in my life that may or may not better the quality of life for me and my family.

I have sold a brand in the past, 3 years ago I sold my first “niche website” for $120,000 and although I was in a rough place mentally when the money came in, it did in fact better the quality of my life for me and my partner, allowing for us to put a deposit on a small house that would have never been possible without the sell.

In fact, I calculated it. The sell propelled our lives forward by 5+ years in terms of affording the property and allowed me to work on Retro Dodo which has also changed my life for the better.

With that in my mind, I keep going back to “what could the sell of Retro Dodo do for my life?”.

The Pros:

• Cash to stress less about finances (pay off mortgage etc).
• More free time to travel with my partner before children.
• More free time to enjoy time with my parents before they get too old.
• The opportunity to start new projects with investment.
• Cash to “setup” the next 5 – 10 years of my life.

The Cons:

• I would have zero income.
• Potential mental health instability (not knowing what to do next and loss of a fun “job”).
• I could regret selling the asset if it grew into something giant.
• I would feel like I let the team down as they would need to find other work.

It’s a difficult question that I honestly don’t know the answer to. I could sell the business and regret it, I could not sell it and be hit by an algorithm update or something that aggressively hits our revenue. I could keep it and enjoy the revenue stream, even though profits wouldn’t allow me to enjoy plentiful time off and travel with my partner on our terms for a while.

It’s a big question, with many risks, but a possible new and more financially free branch of my life, which will allow me to work on new, and hopefully more meaningful projects. A fresh start.

It’s a scary decision, one that I still cannot decide on, even after a year of thinking about it.