I keep going through the same dilemma. I’m writing out my thoughts to help think this through.

I am caught between starting a business or buying one.

Buying a business will help me feel better. I’ll enjoy seeing money coming in.

But then what? If I’m not interested in the business, then I’m sure I will “check out”.

So maybe the better question is, how do I structure my work for enjoyment, connection, and value creation? At the same time, how do I avoid having to get a job?

If my only goal was to avoid getting a job, then buying a business would be the best decision. I’ll have income enough to justify working on the business. I won’t need to worry about the uncertainty of reaching product-market fit and reaching minimum viable profitability.

Even if I don’t enjoy running the business, I would consider it a success, since I wouldn’t have to work a job.

However, the ideal success is running a business that I enjoy. So it wouldn’t be considered a big win.

Shooting for a big win is possible for me now. I have enough savings to shoot for one, and fall back to buying a business later on (or starting a business with more certain cash flows).

Still, it feels painful to not have a decently profitable business right now. It tends to consume my mind at times, and while I still enjoy myself, I can’t help but think that I would be more present and enjoy my leisure time better if I had a profitable business.

It largely depends on my mood at the moment. Sometimes I think, I need to buy a business so I can focus on other stuff like hobbies, dating (for marriage), travel, writing, etc…

But then I think, the whole point is to find work that you enjoy doing and can master. I really want to build a great product, enjoy my work, and connect with others through it. If I buy a business for the purpose of focusing on the leisure aspects of my life, don’t I essentially delay the problem of finding work that I can be really good at and building great products?

And then I think, in that case, I should keep trying to start my own business.

Basically, it is a choice of two adventures: a leisure adventure, or a business adventure.

Buying a business makes leisure the primary adventure. Buy a business, use the money to design a lifestyle that’s interesting, and pursue my interests, hobbies, and travel destinations.

Or, start a business, which becomes the primary adventure in itself. If I’m intrigued by the concept and the potential of the business idea, it becomes an adventure. Leisure adventures would still happen, but probably less often.

The thing is, right now my desire to do great work that I can look back on and be happy/proud of is stronger than my desire for leisure adventures. Following a regret minimization framework, I think I would regret not getting really good at something and building a great product that I’m proud of. I also would regret not contributing to a world I feel has given me much to enjoy.

So can I deal with the pain of no income for the foreseeable future? The lack of a clear role in society, as I try to get new businesses off the ground?

Well, if I’m getting better at executing, then maybe it won’t be so painful. Reflecting on my failures, consistently learning, and getting better, makes me feel like I can build a software business, and that maybe I just need some more attempts and a tighter and quicker feedback loop.

So, I’ll buy a business if leisure adventures become the primary motivator, or if my cash dwindles to the point that I need to buy a business in order to avoid getting a job.

But for now, I’d like to pursue an adventure where I build a good product/business that I’m proud of and try to minimize the (potential) regret of not doing work that I feel good/proud about.

I recently wrote an article on desire tracking. I think keeping track of your desires is a good way to build self-awareness and make better life decisions. So here is a ranking of my desires at this stage of my life:

1. Build a product/business that I feel good about and proud of
2. Avoid the need to get a job (have a sustainable cash-flowing business)
3. Time for leisure (dating, travel, hobbies, adventures, etc…)

Buying a business (almost) guarantees me 2 and 3, at the sacrifice of 1. Starting a business gives me a better shot at 1, at the sacrifice of 2 and 3 to some extent. However, 1 is much far ahead of 2 and 3 in terms of overall desire. Which makes starting a business more appealing (for now).

The next business I’m thinking of starting is a B2B SaaS (business-to-business software). It’s a premium onboarding tool for podcasters and their guests called VibeTrack. I’ll write more about it in another article, but my plan is to build a prototype in 2-3 weeks and get feedback from potential customers to see if there’s anything there. From that point, I’ll either abandon it or pursue it further. The key difference from my previous software attempts is that I will seek validation much sooner.

Anyway, I wrote this to help bring clarity to my own mind so I can stop going in circles in my head. And I think it’s helped.