I always joke with people that founders and CEOs tend to be both workaholics and power-hungry. And yet, as a CEO, I could care less about power (but I do like attention, to be clear) and I am not at all a workaholic. I love to not work.

That said, recently, many of my friends have commented that I work more than anyone they know.  Everytime they say it, it feels ridiculous to me, because I still feel like I don’t work enough.  But you have to wonder, if multiple people are telling you this, maybe you actually are working a lot.

Just the other week, one of my employees told me that they felt like they were in overdrive and at risk of burning out, but not because they were overwhelmed with work. She felt guilty when she wasn’t working, knowing how important it was for our business to push through these difficult times. She said that, since I was online so much beyond the 9 – 6 work day, she felt bad if she wasn’t there supporting me.

The irony of it was, I told her, that I felt compelled to be online more than usual because I didn’t want my team to think that I wasn’t doing everything in my power to propel our business forward. It was an important reminder that, as a founder, the more you are (visibly) online the harder it is for your team to disconnect and be offline. Conversely, as a founder, it can be hard to disconnect if your team is always online.

This made me reflect on whether I had changed my behavior and whether my perception of myself and reality were more divergent than I realized..

Working a lot but feeling like it’s never enough

There were two main experiences that I think heavily influenced my most recent work habits.

First, back in the day, my co-founder and I always used to comment that all the founders we knew worked 24/7 – and worked a lot more than us. There was this Silicon Valley startup mindset that, if we were taking weekends off, we weren’t working enough. And while I still hold weekends (or at least part of them) as sacred, that sentiment has stuck with me. 

Second, one of our first employees, who also happened to be one of our hardest working employees, gave harsh, albeit honest feedback during an annual review. He wrote to me and my cofounder that he didn’t think we were leading by example. That we weren’t in the office enough. Even if we might be working at home, we had a young, green team and they needed to see us working. Like every situation, there is truth on both sides – but there was value in his feedback, especially at that moment in time.

I took that feedback to heart and did my best to act on it and improve. And I did. But, I might have overcorrected.

During our most recent reviews, I asked this employee if he still felt like I wasn’t leading by example. He was taken aback by my question, and said, “that was feedback for a blip in time, no one on the team would ever think you don’t work hard enough now. If anything, you’re working too much.”

This was a formative moment for me.

I had been holding so much stress attached to the notion that I wasn’t leading by example. I care more about doing the right thing than anything else.  As a CEO, it’s hard to always make the right strategic decisions for your business, so I have always tried to focus on the things I can control to ensure I am doing my best as a leader. I had been somewhat terrified that my employees didn’t think I was an active enough steward of Scouted. And while that might sound insane, I needed to hear it from them to really believe it.  

So, how does a CEO or founder actually unplug?

When my team goes out of office, I hold them accountable to extremely thorough ‘out of office plans’. It’s important to me that they’re able to fully disconnect. But, in order to be able to properly unplug, you have to thoughtfully prepare and think through who can handle all of your different responsibilities and ensure that your colleagues are well trained to manage workstreams in your absence.

At a small company, this is especially important. Not only are you likely to wear multiple hats, but it’s unlikely that there’s much crossover within departments or for specific duties. You need to actively plan to take time leading up to your vacation to ensure your team has the information they need to handle your responsibilities well. As a founder, this can be particularly difficult; because, at the end of the day, you can’t really distribute CEO responsibilities across the team easily. Hopefully, you have an executive team that you can lean on. One pro tip I’ve found is to ensure that you are in hard sync with your exec team about what type of messages can be delivered in your stead (i.e. are they addressing mostly tactical business issues, can they address cultural issues, provide meaningful, high-level company updates while you are gone?).

It takes trust, discipline and confidence as a founder to actually disconnect, not check in on slack, and have faith that your team will be OK without you. 

But, they will. This is the team that is committed to helping you achieve your impossible goals; you hired them because of their talent and drive, so let them demonstrate their independence and competence in stride.

I know, that’s sometimes easier said than done. I find there are two helpful tactics that ensure I can actually unplug from work holistically:

1) Go away somewhere without internet or cell service

If you struggle to not check your email, then just go somewhere when you can’t. It’s that simple.  Growing up, I spent my summers as a canoe tripping guide. In Canadian speak, we called it being a ‘Tripper’, which meant that I lead campers on extended, overnight canoe trips in the Canadian wilderness for up to two weeks at a time. My times in the woods were not only my favourite, but my most formative.

It’s something I’ve been missing from my manhattan lifestyle, so recently my brother and I started a new tradition – we now go on an annual canoe trip with our father in the woods the last weekend of August. It’s not only a very special opportunity to spend quality time with our father (we have two other siblings, so it’s rare to get him alone), but it’s also a unique opportunity where I can totally disconnect – not just from work, but from the modern world in a way that I find not only extremely enjoyable but also essential. 

2) Have everyone on vacation at the exact same time

On the other hand, if my team isn’t online, then they won’t email me. 

After running Scouted for five years, it has become clear that throughout every year there are predictable ebbs and flows, times when we will be especially busy and, also, not so busy. So, I decided to take advantage of those slower times to help encourage a culture of taking time for yourself without having to engage with work.

Every year, we close the entire company for the last week of December (this does not count towards anyone’s vacation time) and I have also contemplated doing it either the week of July 4th or the last week of August through labor day weekend. Even if you can’t close down your entire business for a week, I find that long-weekends are a great way to give folks a well-deserved break, enabling them to reset and recharge.

For this upcoming memorial day, I told everyone to take Friday off in addition to Monday. And, to be honest, I did it as much for me as I did for them. I need a break! Knowing that my team won’t be working, means my incoming/inbound flow of requests will be minimal, so I can go offline without worrying about someone needing me.

In general, we follow bank holidays, so I was thinking of maybe changing our policy so everyone gets the Friday off of every long-weekend. Or, at the very least, employing that policy for the time being while we remain 100% remote, as I know that it is harder than usual to disconnect because the traditional barriers between work and home don’t exist.

As business leaders, we have the opportunity to not only lead by example but to help shepherd our employees through these uncertain times. 

And while we are all “out of the office” all of the time now, and there might not be an opportunity to physically travel for a vacation, I think it is even more important to show your team that “vacation” is not only something they can still enjoy, but it is likely something they need to take in order to be able to not just survive but to thrive through these unchartered waters. 

And, even if they don’t need it, you, as a founder or CEO, likely do. So, here’s to the freakin’ (long) weekend…