How to transition from the 9-5 grind to freedom as a bootstrapper

The stair-step approach to freedom

When working a full-time job and trying to transition to living off of our own product, it can be a hard path to navigate.

On one hand, we want to get there as fast as possible, so we’re tempted to quit our job and go all in.

On the other hand, we want to continue to make some income and have a sense of security.

I’ve tried both approaches, and one worked out way better than the other.

The goal, of course, is to find the happy medium between our initial two options. We want to get to our destination as quickly as possible, but also safely. In this case, without going into debt or spending all our savings, and with the best chance of reaching our dreams.

We all have our unique situations. Some of us are living paycheck to paycheck, while others have a significant emergency situation.

I believe for the majority of people, the best way to get there is the same.

Instead of viewing the transition from one extreme to another, from either full-time employment or full-time bootstrapping, we can break this down into smaller steps on the path from one to the other.

There are ways to inch closer to our goal without taking drastic steps.

I call this the stair-step approach to transitioning from full-time employment to bootstrapping.

How I stair-stepped my way from full-time employee to an exit and nomading

This is best demonstrated by example, so here’s what my career has looked like.

It started with a full-time job followed by a cold-turkey, all-in approach to building a business full-time, only to realize that I needed to start generating income again and that a stair-step approach would be more sustainable, have less risk, and create a better chance of success.

Full-time employee

I worked for many years at Adobe as a QA engineer. That is, I tested the software.

When I first started there, I didn’t know much coding at all. I tested the software by manually clicking around. Over time, I taught myself to code and started writing automation tests to have the code test the software.

By the time I left Adobe, I was writing code the majority of the time, but in the context of testing desktop software.

The dramatic approach: Cold-turkey self-employment

My initial attempt to transition to bootstrapping my own products was a drastic one.

I quit my full-time job and went all-in on my own product.

Fast-forward two years and I had depleted tens of thousands of dollars of savings and had one customer.

Lesson learned

Entering startup world

From there, I decided to take a more incremental approach.

I needed to start generating some income, but I still wanted to get closer to my goal.

So I decided to immerse myself in the startup community.

I did this by joining a tiny startup as the third employee. This was my first job at a startup and my first job coding web applications. I was the lead developer and did this for a few years and learned a ton while I was at it.

I was seeing how other people approach building a startup and I was able to gain a lot of knowledge.

I continued to build confidence that I could do this on my own.

Entering SaaS MVP world

Eventually, we got acquired, then a little while later I got laid off, which worked out well because I was looking to make my next move.

But this made the transition easier. I decided to start freelancing as a developer with my target audience being early-stage startups.

I positioned myself as the go-to guy to develop your SaaS MVP quickly.

And while keeping it focused on acquiring early-stage users. This gave me further insights into what it took to find product market fit, get early-stage customers, and start to scale.

All the while I was building applications on my own at night and early mornings and on the weekends. I was determined. And I was stair-stepping my way to where I wanted to be.

I was definitely earning less than I could have had I chosen to go work for a bigger company. But I was willing to make the trade-off for having some income while immersing myself in the world that I wanted to be in.

Upgrading myself through osmosis

Then to get even closer, I decided to surround myself with more people that were further along than me on the journey.

So I decided to start a podcast. It turned out this podcast resonated with a lot of people.

But to be honest, it was a selfish endeavor. I knew that by asking people to be on a podcast, they’d be a lot more willing to talk to me and let me pick their brain than if I just reached out cold turkey asking them if they would talk to me.

It worked out great, and most people said yes. And I was able to pick the brains of people that I admired and aspired to be more like.

Not long after this, I had an application start to take off, generating a good amount of revenue quickly, and I was able to drop my freelance clients over time and eventually had to stop the podcast simply because I was at capacity with growing the business.

Looking back

So when I look back, I’m happy I chose the path I did.

When we feel like it’s all or nothing, we can be tempted to either never make that move to try to shoot for our dreams, or we go all in and risk everything or risk more than we need to and then be forced to give up because we don’t see the results that we want to quickly enough. Or we run out of steam.

By approaching this in a stair-step way, we can more easily inch our way to our destination with less risk and less while acquiring knowledge and skills.

To more easily maintain motivation, if you’re trying to figure out how to transition from a full-time position, I recommend inching your way there versus feeling frozen and not trying or going all in.

Remember to look back periodically and see how much closer you’ve come.

Eventually, you’ll get there.

Like this post?

You'll get weekly behind-the-scenes from my journey to 7 figures: