Benefits of a Workcation

View from Gateway Canyons Resort (Gateway, CO)

As someone who has lived most of his adult years as a bachelor, I’ve enjoyed the freedom and solitude a life apart from a significant other has offered me.

Most years I would take three to four week long vacations alone. And, I probably spent at least 15-20 weekends alone doing whatever I felt like: working, reading, studying, resting, playing guitar or just sitting on a rock thinking.

However, as much as the life of a bachelor is wonderful and fantastic, inevitably someone special comes along and captures your heart and your attention. You find a best friend who you love being with, who (shockingly) loves being with you, and you have a new playmate in life to do many of the things you used to do alone with someone. This brings with it the richness of joy, companionship and togetherness you didn’t have spending most of your time alone.

The flipside of a relationship, however, is that it also, by definition, comes at the expense of your alone time. Your think time. Your study time. Your extended meditation time. Your “working on big thoughts” time. Or your, “I absolutely don’t want to do anything today” time.

[And don’t get me started on how much life change’s when you add kids to the mix as I can only imagine the window of solitude becomes a memory in a far off distant place that you, most likely, have a hard time even remembering. And, for the record, I adore kids and spending time with them — worth every second in my opinion.]

Fundamentally, for me, as someone attempting to lead a fast growth technology company into the future, the solitude, alone time and days of “thinking time” is critically important. Without it, it’s easy to get caught up in the short-term, day-to-day, tactical thinking, game planning and execution. But, when the majority of your time is spent in this quadrant, you’re missing out on the most important work, and responsibility, you have in leading your company.

As the CEO, the number one responsibility you have, is ensuring you have a long-term plan and vision for the company. You have to have a fairly strong and accurate projection of what your industry, and the competitive landscape, is going to look like in five years. You have to understand the macro-trend lines. You have to understand the forces at work. You have to understand what the prevailing headwinds are going to be and also know what the supporting tailwinds are going to be.

You have to study your competition. You have to read into what you think they are, or they’re not, planning. You have to anticipate their moves a few steps ahead and plan accordingly.

You have to know what your strengths are and what your weaknesses are. You have to understand how you’re going to differentiate yourself in the market. To understand how you’re going to take your scarce resources, especially when others have greater resources, and compete against them.

Winning in business is a lot like winning in chess. The only major difference is that, in chess, you both start out with equal pieces. In business, sometimes your competition has more pieces than you and sometimes you have more pieces than your competition. Regardless, as the CEO, it’s your job to maximize and optimize the pieces, the positions and the resources you have to work with.

Business is a fun game. And it’s also a scary game. Success is never guaranteed. And, if you don’t make the right moves and the right decisions, failure is guaranteed.

The sport of business, and the pace of technological evolution, moves faster today than ever. And because of the increase in private capital available to fund ideas and businesses, there’s a good chance you have more competition than at any point in history.

So it’s imperative to create the time necessary to be alone and do nothing but think, read, study, reflect, meditate, dream and prepare for the long-term.

I’ve started referring to these as “workcations”. It’s time alone. And it’s far away and secluded from the office with no one around. They aren’t “vacations” because I spend the entire time, literally, from morning until night ‘working’ — but only on long-term studying, planning and analysis.

Where I used to have 3-4 weeks a year and 15 weekends, I’m carving out two weeks a year and about 5 long weekends.

Luckily, I have a supporting partner in life, who knows how important my company is to me. And how important my leadership is to the company and to all of our employees. And how, if my company is hurting, I hurt. And, if things are going well, I’m a lot better of a partner to her and, granted, a lot more fun to be around in general.

Although I’ve written this from the viewpoint of being a CEO, I don’t think the concept has any less benefit to anyone. Finding that alone time, that place of solitude and reflection, is the healthiest gift we can all give ourselves. It grounds us. It helps us reflect on our lives.

How is my life going? Am I happy? Is there something bringing me down? Is there anything that doesn’t feel “right” or “aligned” in my life? How am I living up to the best version of myself? Is my current life in line with my values? What do I want out of the next five years? When I look back in five years, what will I have accomplished that, when I reflect, I’ll say, “wow, that was a great five years”.

So whether you call it a vacation, a personal retreat or a workcation, finding solitude and alone time is an incredible gift we can give to ourselves and, even more so, when we can give it to our significant others.

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Shawn Riegsecker

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By Shawn Riegsecker