I’ve been having the same conversation with myself over the past few months. Whenever I end up in a cycle like this, I like to write everything down. I think writing gives my brain permission to stop ruminating because it feels assured that I won’t forget. So this time, I’m going to share a little about what I’ve been thinking regarding starting a business!

Why do I keep thinking about starting my own business?

Ownership. I think I’ve romanticized the idea of being my own boss and not having to answer to anybody.

For example, I don’t like having to make sure that I don’t misrepresent my employer – sometimes I talk about things that are important to me, like abuse in the tech industry, and I feel guilty because I don’t want to imply that it’s happening directly to me right now. If I were self-employed, maybe I would feel differently.

Another appeal of ownership for me is not wanting to represent tough policies I don’t agree with. My mentor pointed out to me that one unglamorous part of being an engineering manager is that sometimes you will have to tell your direct reports about some decision or policy handed down to you from leadership and you can’t always say “I think it’s stupid but we have to deal with it.” Sometimes you have to explain and support rationale for decisions that you wouldn’t have personally made. I hate that!

Some people have pointed out to me that even if you own your own company, you’re still beholden to your investors, customers, and employees. I don’t know how to think about this point. Maybe I’d hate this too?

Mission. I’ve written a couple of tweets about how much I want to work on making mental health resources (such as therapy) more accessible for everyone. I think I have some good ideas for how I could achieve this and I think it’s one of the most important things I could do with my combination of skills and interests.

Glamour? I guess I was raised in a culture that puts a lot of value on prestige, even if I hate to admit it. I still wish I could be on 30 under 30. I want to do unique and impressive things.

What scares me about starting my own business?

Stress. I don’t handle stress well. I don’t want to work long hours. I don’t want the pressure of supporting other people’s livelihoods. I don’t want to let people down. I don’t want to feel like I have to be 10x hypergrowth crushing it. I don’t want to break regulations. (HIPAA, PCI, general security.) I don’t want to face pressure from investors.

Not being able to figure it out. What if I decide to go for it, and then I realize that I don’t actually know how to run my own full stack application and I was just too cocky? What if I don’t know how to file taxes? What if I’m not prepared to go to fifty meetings a week? What if I have this grand vision in my head of how this thing should look and I can’t actually execute on it?

What’s the opportunity cost?

I keep dreaming of lots of things I could do, like wanting to be a leader at a large, established tech company, or becoming a senior individual contributor, or switching into a different technical field (mobile? ML?), or becoming a product manager. I wouldn’t get to do all of those things if I seriously think I could dedicate the next ten years to building my own company.

How could I mitigate my fears?

I don’t have to do things the way Silicon Valley has told me things must be done. I’ve been questioning the venture capital / hyper growth narrative and I’m not sure if I fully understand why things have to be this way.

In my mind, the only reason hyper growth matters is because investors want to see major returns on their investments. Of course it makes sense that they wouldn’t want to invest in my lifestyle business if it won’t produce better returns than regular investments. There’s no big reason why I personally need to create a hyper growth company outside of this (I think?).

What would happen if I didn’t take venture capital?

I would need some other way to support myself at the beginning. I would have to have sustainable revenue more quickly because I wouldn’t have the option of taking more and more series of funding. I wouldn’t be able to hire quickly. If someone wanted to take my idea and run with it, they could secure funding and outpace me.

Would I be sad if someone took my idea, got a bunch of funding, and executed faster than me?

Maybe it’s naive, but I think this would be okay.

I think whatever idea I’d end up picking (not necessarily mental health resources!) would end up being something I deeply care about seeing exist in the world.

If someone took my ideas and executed on them even better than I did, I would be really happy that people are getting the help that I think they need. I want more people to find therapy, for example. If I saw a startup that 100% matched my vision of how things could be better, I’d probably just ask for a job there. There are quite a few startups in the mental health space right now, actually. None of them resonate with what I think needs to be fixed. So if I had to make this a binary, I’d say the two paths are that I find a company that matches my vision, or I would feel confident in working to create my own vision.

What would be my ideal future life?

I keep imagining two paths. In one, I run a small, sustainable business, work 40 hours a week, make a reasonable income, and don’t feel immense pressure to match Silicon Valley’s measures of success.

In another, fuck, I’m probably obsessed with climbing a career ladder, working 60 hours a week, pretending I’m not working 60 hours a week, doing a bunch of Personal Branding to seem like a role model to young people… I’m realizing that I have a pretty twisted perception of success that I should examine further at another time.

What could I be doing right now to make small steps towards my goals?

I could be frugal and avoid lifestyle inflation. I don’t live like a broke college student anymore. I think when you start your own company, you should expect to take a pay cut because you’re pretty much creating your own runway. I was happy when I didn’t make my current income, but I’ve let myself get used to a lot of unnecessary luxuries. I used to spend $40 to take the six hour Vietnamese bus ride back to Los Angeles because I was too cheap for the $70, 45 minute flight. Now I throw $40 at a taxi from the airport because I can’t be bothered to sit an extra half hour on public transportation. That’s money that could be going to my dreams! What am I doing!

I could be building sustainable habits right now. If I maintain healthy sleep, diet, and exercise habits now, they’ll be easier to keep up with once things get harder. I’m not doing great on these aspects of my life.

I could be learning more about business development in my personal time. I’ve been getting a bunch of reading recommendations lately and I want to compile them into a separate list! (Too many to list here…)

 

I wonder if anyone else has been thinking about these topics in a similar way? Or is there some big fact of business that I’m missing that would explain why I should follow the traditional startup path?