My Two Year Career Break — the Plan and Results

A career break is a period of time out from employment — Wikipedia

I am currently 20 months into a planned 2-year break. This is the story…

I have always wanted to do a career break. I would read stories of technology nomads or the post-IPO employee traveling the world to ‘discover’ themselves. It seemed like a ‘sweet’ life. Of course, at the back of my mind, I knew it was just a romantic notion. But when the opportunity arose approximately two years ago, I decided to take the leap.

I know I can never ‘leave’ technology behind in this career break - it’s in my DNA.

I have a huge passion for technology and products. Since a little kid, I was always curious about how things worked. I would constantly take things apart, to the frustration of my parents, as I could never put them back together again (there was always that ‘extra part’ left over). So when the Sinclair Spectrum (an early home computer popular in the UK) came out — it was a savior — my curiosity was now contained in electronic bits, out of harm’s way.

Hence this career break will not (could not) be a total disconnect, as I don’t want to lose sight of new trends or discoveries. But I also wanted to take a breather (a break from the ‘start up’ speed that I am accustomed to.) To get away from my ‘start up ADHD’.

The first two weeks, I just naturally veg’ed. It is surprising how focused I was on my career/job without realizing that it took a lot out of me. Then it occurred to me that I was wasting valuable time — a rare opportunity for flexibility. The following two weeks, I read and revisited my drumming skills (like many with rock star dreams, I had picked up musical skills during my teens).

After a month of drifting, it was time to set goals. This was my plan:

Budget. I budgeted for 2 years, for the worst case scenario to cover all bills and no potential income. This removes the core concern of money during the break. Otherwise, it will always be in my head. I had done some back of the napkin calculations before I decided to take the break. (However, I never budgeted for any unforeseen circumstances — see later)

Travel. This seems to be the de facto thing to do and I just love to travel. My plan was to travel at least once a month (prior, I typically travel at least once a year). With the time flexibility — I had a lot of options here. I can take advantage of non-peak time. Less crowd and lower cost.

Read. At least one book (fiction/non-fiction) every month. This is brain food. I always regretted not reading as much as I did when I was young — due to many ‘adult’ things that required time attention. This break was to allow me to catch-up.

Experiments. Explore a new business/technology every 3 months. This is to feed my passion for technology.

20 months into the planned 2-year break…and this is what happened to the plan:

Budget. This went right out the window very quickly. Many factors I did not take into account:

• Inflation. Rent increased over 20% in less than 2 years here in the Bay Area.
• Health insurance outside of company plans are much more expensive (the so called Bronze plans — basic, minimal coverage are in the range of $350-$450 a month — IF you don’t use it. If you do use it — add more $’s).
• Puppy! I adopted a puppy that I had not planned for. Vets became a money pit. (And yes, in classic Silicon Valley tradition, she has her own Instagram following: https://www.instagram.com/its.luna.dog/)
• Injuries. When you have more time, you take more unintentional risks (I love adventure travels — even though my body does not.) This is when you find out that medical insurances in the US is really broken.
• Bitcoins. I ‘invested’ at the wrong time. (Apart from these investment, I do believe the blockchain has a future.)

Travel: I traveled most of South America and Oceania areas. Explored more of the western US states. This was surprisingly much cheaper than I had planned. I took advantage of non-peak time and lots of spur of the moment road/camping trips. With the flexibility of time, I was able to explore more (staying longer when I enjoyed a place or leave early if not). I met many friendly locals (well, my dog did, I was the ‘other’ guy) and hang outs (always an ice breaker when I open my mouth and an English accent came out.) With fewer tourist, I found many deserted beaches and camp sites. Shop owners were friendlier without the stress of tourism. Roads were a delight to drive and I found my love of driving again.

Side note: An interesting thing about road trips is that your music taste is shameless. For no apparent reason, I found that my playlist evolved into 80's music and also pop artists like Taylor Swift!

Read. I averaged more than one book every month. I devour both fiction and non-fiction. Revisiting some old favorites (Robert Heinlein) and discovering new ones (Neil Gaiman — a very imaginative mind). I also discovered that it is better to get UK editions (non-edited) vs the US (edited for language and content.)

Experiments. With the freedom to focus on ideas and not a need to drive revenue, I was free to explore a wide spectrum of business ideas and technology. I created 8celerate Studio for this specific purpose. Some ideas never got further than early proof of concepts. One idea took off early on and there were some very early possible acquisition/partnership talks. This would mean my career break would be over before it got started — so I made the tough decision not to pursue it (I would be lying if I said there was no regret there — but it is a very small one.)

Overall, the career break was a big positive. Like any new venture, it takes a certain boldness and planning — but I doubt if anyone would regret doing it. An unplanned bonus, I got to spend more time with my family/siblings (who are scatted around the world.)

In hindsight, I wish I had planned more time to ‘give back’. I started to volunteer early on during the break — but was never able to commit to a fixed schedule. No excuse. I could have found many one offs.

To be continued…