Full-time to self-employed and what happens next

Sergey Khaladzinski
6 min readApr 3, 2019


It was so quiet and beautiful…

I was laying on my back in the pile of fresh snow somewhere deep in the woods of the Beaver Creek mountain about 11K feet above the sea level and watching the treetops slowly move in the wind… the snowflakes were dancing in the air and falling on my face.

The whole thing felt surreal because just a few short weeks before that I was sitting in the cubicle on the 6th floor of the Grace Building across the road from the Bryant Park in Manhatten, trying to figure out what the hell I was doing there.

What changed before now and then?

Well, quite a lot actually.

If you’ve been following me for a while, you know that I’ve been going through the process of personal transformation. In short, I wasn’t happy with the way my life and career were unfolding, so I set on a journey to uncover a new path for myself, the path that would help me to reunite with my inner calling and remove the ceiling for my future growth.

I know some people were upset by the lack of updates on my blog in the past three months. To tell you the truth there were multiple reasons for that, with the biggest one being a step into unknown…

Yes, at the beginning of 2019 I left my stable and well-paying job at HBO and joined a small fintech startup based in Denver, Colorado as the CTO. It’s a long story how the whole thing became the reality, but the important part is that it did and I had to take some time to get going.

Things like logistics, startup shares, legal structuring and paperwork, accounting soft and payroll for S-corp, home office setup and of course health insurance (not to mention solo 401K setup and ROTH conversions) took pretty much all my attention.

The other reason behind my quietness was losing the WHY… See, for the first time in years I felt like I finally got back on the right tracks so I had to pause and come up with the new direction for my blog going forward.

All of the experiments that I did in the past two years of my life were designed to push me towards the next big step, but when it finally happened I wasn’t sure how to proceed.

When I mentioned my thinking process to my brother Andrei, he simply said: “Don’t overcomplicate, just share what you learn and document your journey!” and that’s exactly what I’m going to do (for now at least, haha).

From this point on, I’ll be simply sharing my story along with some random in and outs collected from the post-full-time world. How does that sound? Are we cool?

Ok, perfect!

Now let me highlight some of the things that happened in the past three months.

I already mentioned that I left my full-time software engineering job and with that came much desired “work-from-home” situation.

The funny thing that it completely screwed up my usual daily routine. I started waking up a bit later every day (not necessarily a bad thing, feels like 8hrs of sleep is my sweet spot), stopped walking to and from the train station (bad), lost my two hours of daily reading time while in transit (very bad), had to cook lunch or rely on my wife to do it (good and bad), reduced my social interactions (good and bad), got more time to spend with my family (very good).

I know that I should’ve scheduled most of the missing items back into my new schedule, but turns out it’s harder than it looks, especially with the little kid running around.

See, when you stay home there is always something to do (and something to snack on). It’s definitely harder to block distractions and there is no hard separation between life and work. More often than not I found myself sitting at the computer after 8 pm just to recoup some lost productivity time…

In any case, I started looking at co-working spaces but didn’t pull the trigger just yet. It’s all about the habits game after all and I’m sure that with a bit of time I’ll be able to come up with something that suits my needs.

By the way, if you have any work from home tips and tricks, feel free to reach out or better drop them below in comments so more people can benefit.

The other big thing happened in February — a month and a half trip to Denver, Colorado. There I spent some quality time with our startup co-founders and enjoyed a nice office with the real doors and walls! (was never a fan of modern open office layouts by the way)

And of course, I did bring my family with me :)

Then there was a short business trip to Las Vegas to meet with potential partners. I say business because that’s truly what it was. We arrived around 10 pm, spent the night in the Holiday Inn close to the airport, had a meeting the next morning and flew back to Denver in the afternoon… No fancy hotels, casinos, wild parties or Bellagio fountains… not yet! :)

A lot of Denver’s winter activity swirls around mountains which they have quite a few. Not the ones we have in NY, but real 14K feet monsters. If you ever heard about world-class ski resorts like Aspen, Vail, Breckenridge and others, well they were all close by.

Fortunately, we did bring our snowboarding equipment and had a blast. The snow just kept coming in and all of the trails including the most extreme ones that I enjoy the most (chutes and glades) were wide open and fun to ride!

Left the car outside for a few nights…

Wild, right? And look, I dramatically improved my snow shoveling skills!

As for the downsides, there was a two hour time difference between Denver and New York which meant I had to do standups with my remote engineers around 7am in the morning… Not the biggest deal in the world, but I had to work around it to fit in my morning exercises and meditation sessions.

That would be all I have to share at the moment, but before I go I wanted to remind you that everything is possible if you set your goals and go after them. You can always change and grow, as long as you are not too comfortable to the point you can’t afford (or forget how) to take risks.

I get it, we all want different things in life, but you still have to push yourself. Trust me, I know how it feels to be on the old rusty tracks. Don’t stay there for too long. Sometimes all it takes to bounce back to life is a simple job switch. Not everyone needs to build and run businesses, but all of us need to experience changes once in a while no matter how good things may appear to be. That’s just human nature.

Without risks, there are no rewards and while I do understand that may start-up venture may crash one day I’m still happy being out there playing the game. Life is a journey, there is no finish line. In the end, it’s all about experiences that you collect and people you meet along the way.

Go get some!

Originally published at The Matrix has you….