Vacations make a business stronger

How we empower employees so everyone – from entry-level to owner – can take guilt-free, stress-free time off.

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For the past two weeks, I haven’t done much of anything. No e-mail, no Slack, no communication with clients or employees. Instead of working on MasterWP’s rockin’ new podcast or shepherding dozens of client projects to completion, I’ve been in Iceland with my wife and son, staying in a Turf House and soaking in hot springs.

I haven’t been “off the grid,” and I’m not taking a sabbatical or shifting to a 4-Hour Workweek. My 17 employees and all my clients have my cell number. But because we’ve built a resilient and supportive system, no one needs to call.

Today, I’ll show you some of the key parts of that system – and how it allows me (the owner) and all my company’s employees to take guilt-free, stress-free time off without our projects skipping a beat.

Paid time off is a right, not a privilege

At Howard Development & Consulting (the parent company of MasterWP), we’ve chosen a different route than most tech companies. Rather than humblebragging about company culture but subtly pressuring everyone to work 60+ hours a week, we are uncompromising about ensuring that our employees have a healthy and fulfilling life outside of work. No one works more than 40 hours a week, and if you log even a few minutes above that threshold, you get paid time-and-a-half overtime.

Rather than “unlimited” paid time off – which requires manager approval and doesn’t have cash value if you leave the company – we have a generous PTO accrual policy (one hour per 11 hours worked) plus 15 paid holidays a year. And, most importantly, PTO does not require manager approval. As long as you have a balance, you simply notify me that you are taking PTO, and you can do whatever you’d like – you own your time.

This always strikes our new employees as weird – they’re conditioned to request PTO and often expect it to be denied or negotiated. It usually takes a few months for people to realize that this is actually a real policy – you just take time off when you need it because your PTO is yours and yours alone. We treat time off as a right, rather than a privilege to be denied at a manager’s whim.

We’re also unopinionated about when and how you take your time off. Some of us like to work fewer hours per week on average. Some take every Friday off. Others save up for a few big trips per year. If you wanted to, you could save up PTO and take three months off. It’s your time and, ultimately, your money to do with as you please.

Notice that, counterintuitively, this more permissive approach makes my life as an owner and manager much easier.

First, I never have to make a judgment call about someone taking PTO, saving both me and my employees untold mental energy and unnecessary friction. This lack of red tape also means we can get the same job done with significantly fewer people doing Human Resources-style work – and when you add in the convenience of using Justworks and PEO Canada to handle employee payroll, HR work for our 18-person team amounts to a few hours a week. (And yes, we have real employees, not contractors, in Canada!)

Second, our entire company is built on the premise that anyone can take a vacation at any time – which forces us to clearly document our processes and set ourselves up to be redundant in every possible way. And because this applies equally to everyone, this documentation and knowledge-sharing is actually a mutual support system among employees: you help your co-workers take stress-free time off, and they in turn help you take stress-free time off. Rather than vacations being a source of resentment and a subject of office politics, as is the case at many companies, they are instead genuinely celebrated as part of an egalitarian system where everybody makes sure everyone around them has the support they need to turn off work once in a while.

The ‘3 Smart People’ Rule

Most business owners struggle with delegation – that is, perhaps, the understatement of the century. Despite all the productivity books and lifehacks out there, we see business owners burn out and flip out every day because they can’t find the balance between caring deeply about their work and empowering their team.

I genuinely enjoy being involved in the day-to-day of my business – both on the MasterWP side and the client-services side – but I also try to be realistic about the limits of my time and attention. To help with that, I’ve developed a highly sophisticated strategy I like to call the “3 Smart People” rule. It says, quite simply:

If three employees on a project agree to something and document their reasoning in writing, it is extremely unlikely that I could have made a better decision myself.

And so, if three smart people agree, I just accept their decision and don’t do anything! Less thinking for me, and far more empowerment for my team.

And this system infinitely scales. Because there is no need to send things up a pyramid-shaped hierarchy, there is no point at which any individual person can be a bottleneck. If I am out of the office, any three employees (all of whom are smart people!) can make a decision without me. If Brian or Nyasha is out, three other people can make decisions about how to fill in for them. Nobody needs to call anybody while they’re on vacation, because we are all sufficiently empowered and cross-trained that we can act as a team to fill in for anyone.

This also works nicely in client communication – for example, when a client has the urge to micromanage. When I frame it as, “Well, we have three smart people on this project, and they came to this decision, and here is their reasoning,” it’s almost impossible for a client to substantially disagree. The team of Three Smart People crushes it every time… and I don’t have to deal with an anxious call from the client while I’m floating in the Blue Lagoon.

Vacation as a practice

Silicon Valley, Wall Street, professional services firms, and many adjacent industries are notorious for treating overwork as a badge of honor. The psychological trap of trading exhaustion for prestige is, in my view, one of the big reasons that many people who are among the most fortunate humans ever to walk the earth are perpetually miserable. It’s also a Catch-22 for business owners – in theory, they can increase profits by overworking their team, but in practice, they often get sucked into the same unhealthy mindset and end up burning themselves (and everyone else!) out in pursuit of a cushier profit margin. They’d be far better off focusing on building a healthy team – which increases retention and morale and creates a team of trustworthy people who are comfortable making decisions without the owner’s direct involvement. A healthy and empowered team may cost a little more – but it means everyone (including me!) can take time off without friction, and that the team will stick together for longer, continuously improving the systems that help everyone live their best life.


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Rob Howard is an editor at MasterWP and the CEO of Howard Development & Consulting, the company behind WP Wallet.

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MasterWP contains no affiliate links. We’re entirely funded by the sponsors highlighted in blue on each article. In addition to MasterWP, we own WP Wallet, Understrap and Howard Development & Consulting.

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