An ocean of opportunity: steering my escape

Henry escaped a career as a solicitor to launch Kraken Travel, a startup marketplace that provides exotic and unique sailing expeditions worldwide. Henry’s need for balance between managing his time, money and personal commitments to create a life that’s his own is a little bit like the ships he sails; a delicate balance of keeping it stable while looking out on a glorious open horizon.

For a long time I battled with what I was ‘supposed’ to be doing and what I wanted to be doing; torn between the pressure to have a ‘proper’ career’ and dreaming about working for myself for ages. Thankfully, I know now that the idea that you can have a proper career is complete rubbish.

Before I escaped, I worked as a solicitor in the city, which made me feel incredibly trapped. On most days, it was difficult to get excited by anything and I really wasn’t relishing the future. I joined the Tribe because I felt like I needed something that kept me accountable; a concrete way to move from wanting to run my own business to actually doing it. Investing the time and money somehow meant that I was taking it seriously and was committed to setting up on my own.

Turns out, the money and the investment were a small part of my commitment. The best things about the Tribe was meeting a load of people who were basically in the same position as me: motivated and ambitious people who wanted more meaning in their everyday. The environment was hugely inspiring – I don’t think even I expected it to be as great as it was.

I made an important and valuable decision to go freelance so that I could slowly put the cash together alongside building my startup. It funds my business, and also covers day to day expenses. But I’ll be honest, not having an income is scary.

Last year my partner and I renovated our house and got married, which was busy and expensive. I had to freelance for longer than I wanted and spend less time on my startup than I intended: but the transition was an important phase. In 6 weeks of working on my startup full-time, I’ve made more progress than I did in the previous year.

I’m finally doing it. On the days I’m in my home office, I’m at my desk from 8am until 7pm. But when I’m not, I’m setting sail to make contacts. I’m off to the Isle of Wight this weekend for the Round the Island Race and then to Norway the week after, where I’m skippering a boat racing to the world’s most remote music festival in the Arctic Circle. In the summer I’m doing a competition in Portugal.

So much of who I am comes from being fiercely independent and loving adventure so it’s awesome that this is now my full-time work.

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You can hear more about Henry’s startup by visiting his website or by connecting with him on Twitter.


Curious about the Startup Tribe programme? Click here for more details. 

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