My First Holiday as an Entrepreneur Terrified Me
“Are you sure?” asked my slightly surprised fiancé when confirming that I had indeed, just a moment ago, agreed to go on a holiday to Hawaii. With a gulp, I replied with unconvincing defiance, “Yes… let’s do it”. That short-lived defiance was suddenly replaced with all these scary thoughts, “Is this putting my start-up in unnecessary jeopardy? Was I being selfish by abandoning my team to go on holiday? What if there was a major incident and I was not around?” That decision felt like one of the hardest decisions that I’ve had to make whilst founding Akagu.
Ten days effectively away from building Akagu felt like a long, long time away from the business. Particularly for an early stage start-up. Does that sound a little absurd to you? It did to me. I mean, talk about first-world problems, where I was stressing over going on a holiday to the quintessential paradise otherwise called Hawaii. I was acutely aware of this privileged position that I was in and yet, I couldn’t help but feel terrified. The rest of this article explores some of the major thoughts that scared me, followed with how I overcame these thoughts on my first holiday as an entrepreneur.
THOUGHT #1: WTF AM I DOING?
This was my first “official” holiday as a founder. That, and the fact that I was almost gone for two weeks — by far the longest time removed from work I’ve had with Akagu. Previous to this, I was an employee who had four weeks of annual leave and I was not afraid to use it. Dare I say, I was even looking forward to it. Now, I had no defined amount of time to take a break, which has led to almost non-stop work for two years. To the extent that weekends and public holidays just meant more days of work for me. Entrepreneurs are known to adapt quickly and thrive under rapid change. This was a new situation that I had put myself in, like some sort of self-imposed intervention or something. It felt very unnatural to not work, like telling a fish to stop swimming and spend more time on land.
How I overcame this
I needed to align this holiday to business so that it felt more natural. I treated this as a ‘one step back, two steps forward’ decision, which essentially translates to prioritising my long-term rather than always yielding to the short-term. Taking a holiday was part of my determination to treat business like a ‘marathon’ rather than a ‘sprint’. Another analogy I like to think of is the fact that despite my love for basketball, I cannot play it 24 hours straight and will need to rest at some point. This was not some random decision made without thinking about the business in-mind.
THOUGHT #2: THE FREEDOM PARADOX
I was suffering from a ‘freedom paradox’, where I could theoretically take a break from work anytime I wanted to, yet this only acted to make it harder for me to take any break at all. People often speak in admiration for our ability to “do whatever we want, whenever we want”, and whilst in theory this is true, we care so much about our business that it can be very difficult to let it go, even temporarily. There is always so much to do when growing a start-up, and combine that volume of work with the unpredictability of a start-up, where any day could be the day you make it, makes it that much harder to break away. Start-ups can be a little like a pokie machine, where your next coin could hit jackpot, so how could you leave your seat?
How I overcame this
“There’s never a better time than now”, was the mantra I had to use to break away from the freedom paradox. Ironically, this was also the mantra I used to get into Akagu in the first place. I had made the decision to take this holiday at the beginning of the year and thought that late March was a good time to go as it was a bit of a make-up for the past two years, and a close enough check-point to reflect on how I was tracking from a business and personal level. I had no idea what Akagu would be like by end of March, which initially created doubt but in the end I thought, it will only get harder if I don’t go now. The other thing that helped was perspective — whilst we feel like we are moving a million kilometres an hour, the reality is that from a market-perspective, most days we move at a glacial pace. This meant that it was highly unlikely that Akagu would die if I went on a holiday.
THOUGHT #3: BUT WHAT IF SOMETHING GOES WRONG?
As CEO and founder, I have many hats on. I am used to doing everything. This makes me a very obvious risk to the business if I am absent because of say, a holiday. This worried me because I am now inevitably going to become a blocker for something, and if a critical incident occurs I may be unavailable for long periods of time. Without a clear direction when even a minor incident occurs, my team could potentially unravel and all of the progress that we had made could all be lost.
How I got over this
This starts and ends with teamwork. I handed over any work that could be easily fulfilled by the team, which mainly consisted of operational work. But to begin with, I also needed to trust that my team members were going to be able to cope without me. Figuring out a way to communicate high priority tasks that required my intervention also takes the stress out for everyone. I was also not fully disconnected and was available online in the evenings.
THOUGHT #4: GUILTY AS CHARGED
Damn, this one is like a punch in the gut. I have a small team with some new team members that had just joined the team at Akagu that would need to ‘man the fort’ whilst I was away on a tropical beach drinking a mojito. It meant that a hard working team would have to work even harder with less direction so that I could take my ‘well-earned break’. I felt very guilty about this and this didn’t get better as I checked my email and Slack when I got back to my accommodation every night. This guilt also extended to all key stakeholders of Akagu — our investor, our labels, customers, etc.
How I got over this
This one was a difficult one, as even when I’m at work I always feel like I could or should be doing more. But like burning myself out, I could risk burning out my team if I am constantly setting an unsustainable pace. If I want to build a culture of accountable work that is derived from both working harder and smarter, I would need to emphasise that you could take a breather too, and the best way to do this is if I ‘walked the talk’. By taking a holiday, hopefully I’m saying to my team that it’s also okay for them to take a holiday or break too.
FINAL THOUGHTS
Entrepreneur.com talks about how holidays have been shown to lead to significantly higher performance upon returning to work. Many say that the secret to maximising productivity is to take time to recharge. I think many people are aware of this but find it hard to actually do it. It’s a similar feeling to jumping out of an aeroplane with a qualified sky diver and a parachute strapped to your back — rationally you’re very safe, but it’s still damn hard to jump. Everything about a start-up involves risk and I still feel like taking this holiday was a bit of a gamble. But I am in this for the long-term and as such I’ll need to have enough fuel for the long haul. I know I can improve on recharging still — next time I should totally detach from checking and responding to email and Slack.
Taking strategic breaks can have great benefits to revitalise your personal life as well. I went on holiday with my fiancé and this was valuable time together that we seldom allow for each other. We learnt how to surf, took challenging hikes, met some awesome people, ate and drank incredible cuisine, kayaked to remote islands, snorkelled and swam a lot, got reacquainted with an old friend called the sun, and dived with the sharks (which I’ll be writing about in my next article). This was critical to recharging, but the novel environment and experiences were also great ingredients to stimulating associative thinking — a necessary and crucial component of innovative problem solving.
Obviously the timing can be important, and you’ll know when best to take time off (e.g. probably not wise to go on holiday at the same time as your product launch), but I wanted to share my thoughts and experiences from my first holiday to hopefully help those that are feeling similarly paralysed by the thought of taking some time off for a much needed holiday.
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