Author Scott Leonard on Freeing Yourself From the Office

by Kristine Hansen

5 min read

In 2011, Scott Leonard began living what for many small-business owners is only a dream: He took a “working sabbatical,” managing his financial-services firm remotely for nearly three years while sailing around the world with his wife and young sons.

“The boat is only moving about 10 percent of the time,” Leonard (pictured) explains. “The rest of the time you’re anchored in a cove or a marina. I would fly home every quarter [for 10 days] to visit with clients.” During those trips back to the U.S., his family stayed with the boat.

In November, they all returned to California, where Leonard owns Navigoe in Redondo Beach. He felt refreshed and energized. He’d also learned how to run his business, which employs four other people, while he wasn’t there.

Leonard shares his journey in the new book The Liberated CEO: The 9-Step Program to Running a Better Business So It Doesn’t Run You. He recently chatted with the Intuit Small Business Blog about the pros and cons of taking a working sabbatical.

ISBB: What are the side effects of a small-business owner taking too much responsibility for his or her company?

Leonard: It’s burnout. When you start your business, you’re gung ho and working incredibly long hours because you’re really excited. You can’t maintain that pace.

What can suffer are your family relationships. When my first son was born, I was meeting with clients who are retired business executives and they said, “Don’t do what I did and work too much and not spend time with your kids.” That really resonated with me.

Are you giving your staff the growth that they need to graduate? A lot of people don’t want to share their job (and the details of what they do) with others, because they see it as job security. If you do everything, you can’t really promote yourself up within the company. You’re not letting anyone else move into those jobs, either.

Your best employees are not going to work for you for 20 years doing the same thing. You’ve got to give them the ability to move up.

What first steps did you take to start running your business remotely, from the boat?

I designed the company before I left to be stable while I was gone. [My advice:] Delegate as much of the business to the employees as possible and have the business set up to run without you. Determine what you, as the business owner, are best at — and only do that activity. When you’re operating in the zone of what you really enjoy, you’re extremely efficient.

For me, the goal was to free up a lot of time. For other business owners, it may be leveraging their time better. My goal was to leverage (using software and administrative help) everything that goes around preparation for and follow-up on meetings, so all I really do is meet with clients. You want to outsource everything that isn’t literally touching your client.

On the sailboat, we had satellite for phone and broadband internet at dial-up modem speed. Incoming text messages (from my employees) told when I had to deal with an email, as it takes a lot of juice to turn on the satellite. Ninety percent of the time, we were by an island. I bought a SIM card for my phone. Everywhere in the world they’ve got cell phones now, including an archipelago in the South Pacific that has no electricity and where locals have tribal dress and get around in outrigger canoes.

In your book, you talk about the “feed it fat or kill” process. How can this be applied to business?

Entrepreneurs are problem solvers. We see something going on in the world and think we can make it better. It’s the curse of being an entrepreneur. You start to have these tugs at your energy and your time to want to go to other things. This could be what you’d do in your two-month sabbatical.

You either need to go and pursue that or … let it go, cut it free, take that working sabbatical. Maybe you come into your company [one day] and say, “For the next two or three months, guys, I’m unavailable. I’ll check into the office a couple of times a week, and if there is really an issue, give me a call.”

This isn’t about getting on a sailboat. It’s about giving two months to pursue it and see where it goes. The great news is that you’ve already got your business giving you revenue.

Most successful CEOs have, at one time or another, taken a sabbatical. How does this lead to long-term health for the company?

You get to step out of the day-to-day minutiae of the firm and recharge your batteries. You’re releasing yourself from that big to-do list, and you’re only there if something urgent needs to be dealt with. It allows future leaders of the company to step up because you’re not there as the go-to person. If you’re always there as the go-to guy, nobody has the opportunity.

I like to use this basketball analogy: When the superstar is on the floor, everybody looks to the superstar to make that last winning shot. When the superstar isn’t there, it’s obvious that someone else will step up. Most entrepreneurs tend to be big personalities and have big shadows. When we step away, that shadow’s gone. It gives other people the opportunity to make that decision.

Go take a one-week vacation without your smartphone and tablet and without checking in to the office. You’ll find out what’s broken really quickly when you’re gone. Make an employee take a two-week vacation and put someone else in his or her role. It takes two weeks to find out what’s been going wrong. Who can step up and who can’t? Who’s capable of making decisions?

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