I was invited to speak at a webinar by the Estonian e-Residency team. I spoke about productivity challenges specific to those with a flexible lifestyle — like the digital nomads that often use e-Residency to form their companies. Though in 2020, the advice could also be relevant to those in (what are normally) traditional jobs.

Below is a written up version of the personal background I gave at the start of that talk. I’ve made similar writeup for the talk itself: Productivity Challenges Specific to Flexible Work.

Hello I’m Kaitlyn. I’m the owner of the productivity software company Simply Digital that makes the to-do list app Simply Goals & Tasks. Mats (our host from e-Residency) says there is interest in getting started, so I’ll give an extra minute for background before moving onto my topic of productivity challenges specific to solopreneurs. Then, of course, there will be Q&A or you can even email me.

The first stage of my career was quite traditional (at least, for an American who wants to work in software). I went to Northeastern University, got a Computer Science degree. Then moved to San Francisco to work as a Software Engineer at Adobe.

Then, as a 23 year old, earning 6-figures, and with virtually no personal responsibilities — the world was completely open to me. And I realized what I wanted more than anything (especially before I had those personal ties, like a partner or children or a mortgage) was to do more long-term “slow” travel. Basically, not just to take a vacation to all the places on my travel-bucket-list but to live there at least for a short period.

Therefore, I plotted and planned for a year. I sold things, did financial prep like changing credit cards to ones without foreign exchange fees and a bank without foreign ATM fees (I recommend Charles Schwab), learned about freelancing, took Italian classes. And finally I quit my job! Essentially starting phase two of my career.

What happened next was a lot of fun! I drove across the US; went to Oktoberfest; visited and traveled with friends all over.

But professionally, even with the advantage of money and valuable skills (I’d like to think) and all that preparation — there was a lot of failure in the beginning. In hindsight it was because:

  1. First off as a software engineer, my skills are quite generalist while also technical; I had a hard time communicating what I could do in order to sell myself. So, just more difficult than I anticipated to find clients.
  2. Also turns out starting a business is a lot of work. Maybe you can do it while traveling, but you can’t do it while on vacation.
  3. And finally even when I stayed in one place and had time, I really really struggled with productivity, which was new for me. I had never struggled with getting things done; but being productive when self employed is so different than when in a traditional role.

That last one would be a perfect segue into my actual topic: productivity. But of course I can’t leave out the E-Residency part of my journey.

I did contracting as a “sole proprietor”, which is a US business structure that requires nothing; there is no paperwork and there is no line between Kaitlyn Hanrahan the human and Kaitlyn Hanrahan the business.

When I decided I didn’t want to continue contracting and wanted to try being a mobile app developer, I needed a business structure to legally separate me from my company. Normally that’s not too complicated — but if you don’t have a permanent “country of business” then it becomes insanely complicated. At the time I was getting great business consulting for free from the US SBA. But when it came to anything legal, they would refer me to a lawyer, and the lawyer would want to refer me to a more specialized lawyer, until I was talking to international business lawyers that I absolutely could not afford. Basically hitting a dead end.

All the time wondering — I’m not the first to do this digital nomad thing, how does everyone else do this?! And I finally found that answer when I stumbled across a blog post from Xolo and learned about Estonian E-Residency.

Xolo is my provider now. I can’t compare them to the others, but I’m a very happy customer.

I’m lucky to be in Rome, Italy where there is an Estonian embassy. I’m already on my second Digital ID Card. Both times I was in and out of the embassy in less than 10 minutes.

For my business checking, I actually went quite a while without one. Just having expenses be “out of pocket”. But then I won an essay contest where the prize was a paid trip to the Latitude 59 conference. While I was in Tallinn, the Xolo people organized my appointment with LHV Bank as well as having my new bank card mailed to me afterwards (which wouldn’t have been possible without an intermediary), and that account integrates nice with the Xolo interface.

It was also a really fun trip. I hadn’t been aware of the community around E-Residency. Which now is even easier to access, you can just join EERICA. And Tallinn is an absolute secret gem of a city.

The talk continued on to the actual topic.

Categories: ideasour companytalk