One week after my son was born, I became jobless. On purpose.

became jobless

One week after my son was born, I became jobless. On purpose.

Drew Thomas is an entrepreneur, investor and advisor. He’s currently working on an ecommerce platform called Really Simple Store. He previously cofounded and ran Brolik, a digital agency, as CCO and then CTO. He lives in Austin, TX.

One week after my son was born, I became jobless. On purpose.

I’d spent a decade plus owning and growing a digital marketing agency, and it was time try something new. My own thing.

If you’re ready to go out on your own as well, then we’ve likely read some of the same articles, listened to the same podcasts, and follow similar people on Twitter. You know the stuff… inspiring people and stories around enjoying life and making lots of money doing it.

It can seem easy to transition from a subject matter expert into an expensive consultant who sets their own hours and makes their own salary.

After going through it, I can tell you it’s definitely NOT easy, but more importantly… I think you should still try to do it.

The key is to plant a lot a lot seeds.

Real life

No one told me that going out on my own would be really hard and really slow at first. It was a total shock, but it’s actually logical, so that fact set in pretty fast.

Once I accepted that it was going to take more time than expected, I adjusted my plans and finances to accommodate. I got smarter about selling and marketing myself, and I started organizing my days for productivity.

I wasn’t super far off. I had some clients, and I made some money, but soon, I was tapping into savings… and getting frustrated.

Eventually I was fantasizing about getting a job in the way I used to fantasize about leaving my job.

I thought my new career status would give me more time to work on fulfilling side projects… but I had less time than ever.

Eventually, after cashing out my IRA to pay the mortgage, I gave myself an ultimatum: I would say yes to everything for one month, and if nothing changed, I’d search for a nine-to-five and give up working for myself.


I believe that this mindset is what ultimately brought me through that period into today, where I’m fairly successful and definitely on my own.

Of course, there are a ton of other factors, and everyone’s path is different, but to say “yes” to everything is to literally create opportunity. The only way to grow is to do, and I’ve found consistently that even projects where I don’t get paid come back and help me in the future. (I can’t emphasize that enough.)

Within the first week of my ultimatum/experiment, I said yes to something I would otherwise never have considered. Lots of red flags. But it bought me a few months of critical runway at a time when I needed it. Even though my original instinct was ultimately correct, saying yes allowed me to continue pursuing my larger goal, which was an important lesson for me.

It wasn’t just the financial runway, either. I got other work through people I met from that original job. I also learned things and tried things that make me a better consultant today.

Success is the sum of all the different opportunities that you take advantage of. The more you do- the more seeds you plant- the more chances you have for something to grow.

This was true for me while not finding a job, but it’s also true of finding a job and growing in a job role. We can’t predict the future, but we can put ourselves in the best place to take advantage of whatever happens.

Read more: How I Got My Dream Job In Cybersecurity

One week after my son was born, I became jobless. On purpose.

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