We Brits call it a “holiday”; Americans, a “vacation”; you might call it something different.
Whatever you call it, the Oxford English Dictionary defines it as: "a period of time when you are not at work or school; a time of rest and enjoyment."
And Merriam-Webster: "a period spent away from home or business in travel or recreation."
Pretty much the same thing. Whether you travel near or far, it’s about switching off from normal life to recover, recharge and have some fun, whether it's camping a few hours down the road or two weeks in the Maldives.
Summer has arrived early here in the UK, and yes, we're now all complaining about how hot it is (you know how much we love to talk about the weather), and we're at the start of the “holiday season”. I know that some of you will need and take a proper holiday, and some of you will go on vacation, but your attention will be elsewhere half the time. This letter is for both of you…
A former boss of mine used to wind me up that I “had more holidays than Judith Chalmers”. If you grew up in the UK, you'll know Judith was the host of a TV show called 'Wish You Were Here', where she jetted around the world, showing us beautiful resorts and making us want to book our next vacation. In my research for this letter, I sadly learned she passed away just a few days ago, aged 90, having lived what her family called "an extraordinary life.“
Honestly, I always took that comment from my boss as a compliment. One, if I were going on holiday again, I would have to be performing and earning enough commission to treat my family. And I've been consistently going on holidays each year, and my career continues to advance; it’s clearly a key component of my strategy that must remain in place over the long term.
And maybe there's a lesson from Judith Chalmer’s, too. She worked hard and successfully, did something she loved, saw the world, and made it to 90 surrounded by family. That's a pretty good way to measure a life, in my opinion.
A holiday shouldn’t just be a reward for delivering results. It's not something you should only do if you’re having an outstanding year vs quota (I’m of course not suggesting you put yourself into any financial difficulty). But a break, recovery is vital for performance. For your body, your mind, and for those people you’re doing all this for, who will still be present in your life, hopefully, when you are 90.
I’ve said it before, you can’t keep sprinting indefinitely. You'll run out of steam. Just watch some of the players who will be playing in the World Cup this summer; some are currently getting much-needed rest before an intense international competition. Some have played 60 games with no winter break and still have a Champions League final to play on Saturday. Undoubtedly, some players will be running on empty; we’ve seen so many global superstars not perform in major summer tournaments like this before. Especially England fans like me!
And the same applies to you and your sales career. And I have to admit I spent chunks of my career on both sides of this.
One year, I spent every morning of a ski trip that clashed with our year-end with my laptop out at 6 am before everyone else got up, and we headed up the mountain. Checking invoicing against my number, replying to emails, and then thinking about the deals that still needed to get over the line all day, taking sneaky looks at my phone between runs and après.
On the flip side, one of the best vacations I've ever had was a three-week trip to Mallorca. My youngest was only 3 months old. I didn't send a single email, join or answer a single call, or respond to a Slack message. We relaxed, had fun, enjoyed beautiful food and drink, had family come stay with us, and cycled some of the island's beautiful yet brutal climbs. I was completely there on that holiday, and guess what, when I came back, everything had continued just fine without me. The team had stepped up, deals had progressed, and I still got promoted just a few months later.
I’d programmed myself into thinking and feeling that I had to work while I was away, so I did. And that the team will always need my help to get the work done or make decisions. Well they didn’t, certainly nowhere near as much as I thought they did.
Choosing to work a lot (or even a little) on holiday doesn’t make you a high performer. It also doesn’t make you a low performer. What it does evidence, though, is that you haven’t built a team of people around you that you can trust, or the mechanisms/structure required to confidently hand over the reins for a short while.
I’m not advising you to disappear and just chuck the keys to your colleagues. Before your next holiday, you’ve got to do the prioritisation, preparation, and communication - a concise, focused handover document does the trick. You’ve got to secure buy-in from your team and have them briefed and confident of what success looks like while you’re out. And set clear boundaries: You won’t be checking in, and if you've missed something or there’s a genuine emergency, they can contact you. And I promise they’ll respect your boundaries, because you’ll respect theirs when it’s your turn to provide cover. Over 13 years in the corporate world, I was contacted only once, when a CEO reached out to AWS’s CEO out of the blue. Trust your team. Show them how much you believe in them; that’s one of the strongest pieces of recognition you could ever give.
I'm heading on holiday in a few days. Business brain will be dialled down, and family brain will be fully turned up (you don’t get much rest with two boys under the age of 8). We’ll have fun, no doubt eat and drink too much. I’ll probably have to break up the odd scrap, but I’ll love every second of it because there are only so many summers that your kids want you to throw them around in the pool for (what feels like) 12 hours a day.
The deal, your career and your reputation will still be there when you get back. This opportunity for recovery and moments with your loved ones you won’t get back.
Go and enjoy it. Be present. Come back energised and ready to have an even greater year.
-Aaron