Imagine a life where you dictate your own schedule, free from the confines of a traditional job.

That’s a thought experiment I’ve been playing with lately: what would it look like if this was my last ever job? How might I optimize my lifestyle for freedom?

By that I don’t mean that it would be the last time I needed to earn money. I work in non-profit news; nobody does this because they want to become rich beyond their wildest dreams. Even tech salaries feel distant from this vantage point. To be clear, I’m doing this work because it’s important, and I have no plans to leave.

Regardless, I think it’s an important thought experiment. What if this was the last time I worked a job with regular hours and a boss and a hierarchy? What would it look like to have a lifestyle that was less bound to working norms, so that I could choose how to spend my day, or my week, or my year?

This desire to seek a lifestyle less bound by traditional working norms is shaped by two big influences:

• My working life in startups, which was very much self-driven
• My own parents, who had their own publishing startup for a key part of my childhood.

My parents’ ability to dictate their schedules and norms meant that I was able to have childhood experiences — in particular, trips to mainland Europe and the US — that would have been much harder otherwise. (These things didn’t need all that much money; they needed time.) That lifestyle did something else important, too: it showed me that it was attainable, and that a person doesn’t need a 9-5 to live. That perspective, in turn, allowed me to become a founder and build new things.

I would like to do the same for our son. Honestly, selfishly, I would also like to do it for me.

What are the roads to more independence when you aren’t independently wealthy?

Here are some options I’ve considered:

Startups

The first potential path to independence is through entrepreneurship.

I’ve founded two startups in my life. The first one was bootstrapped for the first couple of years before raising a round from British investors; the second was kicked off with a small amount ($50K) of accelerator seed money.

My life has changed since then. In particular, my capital needs have shot up. There’s a child and daycare and a mortgage in the picture, which is radically different from my life as a twenty-something prepared to live on Pot Noodles and scrape by with little money. A working life of open source, mission-driven startups, and non-profit news means that my savings are meager and wouldn’t support a new venture. A friends and family round is out of the question for me, as it is for anyone who doesn’t come from wealth.

Building a startup means working hard on it while holding down my day job, until it reaches the point where it has enough traction to raise a seed round. The barrier for that traction is rising steadily; it probably needs to be making tens of thousands of dollars a month for a seed investor to find it interesting. Still, that isn’t insurmountable — particularly with a co-founder. I have more product, engineering, and organizational growth skills than ever before, and I believe that I could do it.

But also: at the point where it’s making tens of thousands of dollars a month, assuming a low running cost, that’s more than enough to sustain me! It doesn’t need to be a high-growth startup. It could be a small business that is content to do quite well. A Zebra, perhaps. The disadvantage is that the upside is limited: it’s unlikely to make me wealthy beyond my wildest dreams. But what if that isn’t the goal? If the goal is freedom, a modest income is wonderful.

Consulting or Coaching

I have coaching training, and I’ve previously coached founders across a portfolio of mission-driven startups. In many ways, my roles as a CTO / Head of Engineering / Director of Technology have been largely coaching-based too: effective 1:1s and frameworks for feedback are the lifeblood of building a team.

I’ve also got strong product design and design thinking training, and have run workshops and design sprints with many teams. I understand product fundamentals, how to instill product thinking in a team, and can shepherd a product (and product team) from insight to launch.

And I’m technical. I can architect software and write code; I can advise teams about how to think about new technologies like AI, or how to build their own software. I’ve done this in many different contexts, many, many times.

So I think I can offer a lot. The challenge with consulting of any kind, though, is that it’s essentially a freelance job: you’re working from contract to contract, or from session to session, which means that you’re constantly having to sell yourself for the next thing, at least until your reputation has reached the point where people are asking for you.

Perhaps a retainer model would work: enough people subscribing to receive your attention and you have a steady income. Too many, though, and you can’t support them all. Too few, and you need to be in sales mode all the time. Still, it seems attractive from the provider end; the question, of course, is whether any customers would actually go for that. My guess is probably not — at least until you have enough glowing referrals.

Selling Products

In a way, this seems like the most attractive option: sell a finite product that doesn’t require your direct involvement, so that you can spend your time building the next product to sell, until you have a portfolio of products that sell without you and generate a reasonable income.

There are plenty of influencers who peddle “passive income”. My strong belief is that they’re all scammers, and that the dream of financial independence is what they’re all actually selling. Still, there are clearly people who sell things on the internet, and some of them do quite well.

These include:

• Books: Yay for books! Of course, the idea that you’ll make an income from books alone is a pipe dream. Even bestselling published authors often don’t leave their jobs until they’ve had a few successes in a row. There are more books being published and it’s harder to break out. Full disclosure: I am writing a book! But I don’t expect it to cover my costs. I’m doing it because there’s a story I want to tell. (And then I’ll do it again, because there are more stories to tell.)
• Courses: Do people really make a lot of money from these? I mean, maybe. It feels like courses mostly fall into the same category as books: something you do because you want to share some knowledge or potentially demonstrate some expertise, but not something you do as a money-making venture in its own right.
• Apps: Hmm. This was a great idea in 2008. Some software really does support independent developers, though — but my suspicion is that the software that does the best are actually services, which fit better into my “startup / small business” description above.

A Portfolio

I think this is the real answer: it isn’t just one thing. Likely, a repeatable income is cobbled together from threads of at least some of the above elements: building a service, offering coaching or consulting, and selling individual products.

One danger here is that attention is spread too thinly: because multiple threads are required, you necessarily have less time to spend on each. Consequently, the quality of each element may suffer.

This approach no longer puts all eggs in one basket, which means there’s (in theory) more tolerance for one thread to fail. But it also means that you’re spinning plates in order to try and keep them all working. Because there’s less time for each, and attention is split, there’s a real chance of all of them failing.

Still, overall, it feels like the most resilient approach, with the most room for experimentation. It’s by no means the least work, but minimizing work isn’t the goal: that would be maximizing freedom, which isn’t the same thing.

What do you think? Have you made this leap? Did it work for you? I’d love to learn more.