Being a CTO in a startup or scaleup is a demanding job - strategizing with your fellow CEO, motivating and mentoring the tech team, getting your hands dirty to ship the latest feature, keeping an eye on recruitment, evangelising the tech product with customers and investors...the list can become quite long.
Sometimes a CTO feels too busy or with too many important tasks that need finishing to even consider taking the time off. And even if they make it on holiday, the CTO may end up taking their laptop with them, check their email often and participate in slack discussions when they should be relaxing.
I have to admit I have been guilty of the above - typically justifying it that everything relies on me personally otherwise it won’t get done (which could be true, but shouldn’t be the case in the first place) or that I’m simply loving my job (which is true, but not relevant)
The work/life balance has become this mythical creature that everyone strives for, not few manage to find. Are we working for a living, or living for work? The truth is probably somewhere in between: some of us are very lucky to love their work, treating it rightly as just a part of their life. However we have to be aware that’s not the case for everyone, and jobs can play different roles for different individuals. And even if it is the case the benefits of having a complete break pay dividends for you and the team.
Fear vs Trust
Yes, we’ve all been there - there is always a project that’s too important to be left for others to do. What’s easy to forget is that, although in the short term it may be beneficial for the task at hand, there are important strategic consequences of such an approach.
Your team will perceive such an approach as lack of trust in their ability, affecting long term company growth prospects and team morale.
The fear of losing control will become obvious to the internal team, and the stakeholders and investors - identifying it as a bottleneck that needs to be addressed.
The ONLY way to give the opportunity to your team to show you their maturity and skill is to trust them to move things in the right direction when you’re not around. Remember that low level tech task that you kept doing because it was too important to be left to others? Well, it has been done beautifully while you were away, with excellent communication and now there is someone else who can do that in your absence.
Or, that client meeting you force yourself to attend in the false belief that it was YOU that ensured smooth communication and team engagement - well, your team has managed to surpass that, building the relationship they can manage without your constant supervision going forward.
Time for Big Thinking
However there is another, arguably most important aspect of ensuring you find a time for proper holiday: a time to think. If you really relax, leave day-to-day work tasks aside, you're freeing your brain to think about long term strategic points. Thinking about what you need to do to grow as a person, as a technologist and a leader over the next 12 or 24 months.
Sometimes people in senior positions are reluctant to take a holiday because they feel it would harm their careers - not being there when that project opportunity arises or when that critical outage happens, or god-forbid if things go so smoothly so your expertise is not missed at the company.
But that's another false thought - your role is to think strategically, build a long term technology vision - there is no better time for that then when’re on holiday, catching up on all those books you didn’t have time to read or getting small doses of wisdom and inspiration from non-work related conversations with people you didn’t have enough time for.
The truly innovative ideas, those that drive the key change of the product or an organisation, will come to our mind when we’re free of burden and allow the thinking space and time.
Unlimited holidays is one of the tech job perks that has been quite popular for a while - the libertarian mindset to take as many holidays as needed, whenever it’s needed. The experiment largely failed, and not for a reason of everyone taking time off all time and no one being around to do some work.
It’s the fact that people with key skills and in critical roles weren’t taking enough of it - the lack of holiday scarcity and the fact that they enjoyed their work, made them less likely to commit to holiday time, without external pressure of losing valuable holiday days.
There is psychology at work there, but what’s important is that everyone takes time to recharge, have good rest and come back to work refreshed, with new vigour and ideas.
With that in mind, the Pragmatic CTO is off on holiday - away from the day to day work routine, not checking their email and sipping espresso in the palm shade somewhere. But still working - working on personal relationships, life goals and practicing blue sky thinking that will inevitably find its way to their working life, just not in the usual way.