As many of you know, on April 4th, 2018, I stood shaking with nerves in front of the Skimlinks team, and told them that I was stepping down as CEO. After over 10 years of dedicated and passionate work, I had made the tough decision to bring on a new CEO better suited to the next stage of Skimlinks’ journey, and take some time to rest and recuperate before once again (likely) diving into the fray of early startup life.

That day – April 4th – was also my last day in the office. These kinds of transitions are best done swiftly with minimum ambiguity and fuss, so the team can quickly adapt to the new leadership. And so ensued my “sabbatical”.

I called it “my sabbatical” because, frankly, it sounds a little less flippant than “I’m deliberately unemployed!”, and calls to mind more intentional and thoughtful journeys of self-discovery. Which – I knew when I wasn’t being deliberately flippant – is what I wanted this next period of time to be about.

How long would this period of time be? I kept being asked, but how could I be precise about something so ineffable as “a learning and healing journey”? I knew I didn’t want to rush into anything serious or full-time for many months, at least 6, but I also wanted to deliberately remain uncertain for as long as my human heart could withstand it.

As I would say often to people during this period: “Humans find vacuums uncomfortable, and develop a strong urge to fill the uncertainty of that vacuum with certainty. However, the longer I can withstand this pressure to cave in and the larger I allow the space in the vacuum to become, then the larger and more special the object I make space for in my life.” I also would frequently: “There are precious few times in our life when we are in a state of complete transition… maybe after high school or college, maybe once or twice between major life events or career breaks… so when we are in the midst of such a state, rather than wish it away with worries or impatience, embrace the discomfort of uncertainty with patience, and relish the rare and exquisite feeling of being in transition. All too soon my life will be filled once again with certainty and busy-ness and too much to do… so for now, when I don’t have any responsibilities, anywhere to be, anything to do, I can just be me…. whoever it turns out that is, once the CEO tag becomes less defining.”

I knew I wanted to travel, and started to compile a list of all the places I wanted to go. I wanted to experience living in different places too, to see if maybe I should leave London, because heck, I wasn’t tied to it any longer! I wanted to learn lots of new things, through books and courses, as well as through physical experiences. I knew I wanted to finally create a blog and share thoughts and ideas that I never had time to do as a CEO. I knew I wanted to play with new business ideas, and boy oh boy did they start to gush forth with creative urgency and hilarious diversity! All of a sudden, I felt myself completely overwhelmed and at the mercy of a mind fully untethered for the first time in a decade. It wasn’t pretty… loved ones around me would initially laugh then get concerned that I was whipping myself into an anxious fuss over something that really was quite joyous.

So I decided to take action, and capture it all down… every idea, every dream, every ambition… I worked out how to use Trello (visual task management software) and then documented all my dreams in a series of Trello boards: one for my new business ideas, one for my blog, one for my travels, one for my learning & development, and one for life admin.

My many Trello boards, obviously blurred for my privacy and your surprise.

Getting my wild tirade of ideas documented into an organised structure immediately calmed my anxious mind, and I set about filling my days with trying to tick off items. That first month after I left Skimlinks, I had a lot of meetings to explore some of my new business ideas and did a lot of life admin and home tidying. I caught up with old friends. I read books. I had long lunches. I planned and ideated.

However, I felt myself getting pulled inexorably towards some of my more enticing new business ideas. I knew if I didn’t divert my path, I would cave into the pressure and fill in my vacuum of uncertainty. So I booked travel. Lots of it.

And it worked. I had the most incredible ‘Summer of Love’, where my life changed and lifelong dreams were achieved. Where I fell in love with myself, my dream man, and life itself. Where I found healing, strength, and the energy to do it all again.

I’ll share the tales and discoveries of these travels now. Hopefully these will be both inspiring for your own life and informative for your own travels.