How to quit your job. (First, know what’s next.)


July 20, 2018 

I confess to getting a gnarly, antsy — almost dreadful — feeling in the pit of my stomach Monday mornings, when I begin my two-mile walk from home to work.

It started after I hit my 60s (I am 62 and 10/12 ). I get a feeling like, well, is this the best use of the time I have left?

I’ve been writing a lot about retirement, estate planning, long-term care, wills and other golden-years stuff, so I phoned one of my sources, the career coach and serial job-seeker Bob Fleshner, to ask what was going on.

“What you are feeling is extremely common and not only limited to people as they approach retirement,” Fleshner, 63, said. “It could be you feel like you are running out of time. It could be you hate your job. [I don’t.] Or it could be something different. But it is something you should examine.”

Fleshner knows what he’s talking about.

At last count, the Boston University graduate has had at least five careers, including two prestigious ones from which he walked away.

Fleshner was a top lawyer at Feld Entertainment, one of the world’s biggest producers of live shows (“Disney On Ice,” “Monster Jam,” Supercross and the late, great, Ringling Bros. and Barnum & Bailey Circus).

He was also the chief executive of UnitedHealthcare of the Mid-Atlantic, where he commanded a staff of hundreds and oversaw more than $300 million in revenue. (He also worked at a business development company and — get this — he ran a profitable local business that organized overnight relay races.)

Why on earth did he leave UnitedHealthcare after more than four years, and after turning a money-losing operation into a profitable one?

First off, the timing was right. UnitedHealthcare of the Mid-Atlantic went through a couple of mergers, eventually triggering Fleshner’s right to a year of severance pay. He chose that rather than risking a transfer out of the Washington area.

He was also tired of the corporate gig.

“Here’s what went through my mind: I was CEO, but I don’t get to make my own decisions. I still have to report up. I wasn’t running my own company. I was employee 000117588. I had to do everything the corporate way. Lastly, at Ringling, I was the guy everyone wanted to talk to at the cocktail party. At UnitedHealthcare, I was the one everybody hated. People hate their insurance companies.”

After being a corporate lawyer and running a big health-care insurance division, money wasn’t an issue.

“I didn’t have Bryce Harper money, but we were comfortable enough that I could be flexible,” he said. “My wife works. We always lived well below our means, and continue to do so today.”

Fleshner drives a Ford Fusion Hybrid with close to 100,000 miles on it. He funded the kids’ college education early on, so that wasn’t a worry.

Fleshner said the real issue in walking away from your job is whether your career is correlated to your self-worth.

“If you define yourself by what you do, it can be tougher to change course,” he said. “I have a client who is 66 and runs a $100 million enterprise. He’s hoping to retire soon, but the prospect terrifies him. He recently said to me, ‘Who am I if I’m not running my company?’ He’s an extremely successful businessman who has absolutely no sense of self beyond his profession.”

That’s not uncommon.

Psychotherapist Bryan Robinson, author of “#Chill: Turn Off Your Job and Turn On Your Life,” counseled one multimillionaire client in his 80s whose wife left him after 35 years because he could not tear himself away from the office.

“He loves the status,” Robinson said. “A lot of it has to do with these people with big egos who don’t have a lot of spiritual or deeper connection with who they are. Material trappings and success have a stronger appeal than relationships. They haven’t built another life. Work is all they know. ”

Recently, I attended a small party for a co-worker who was retiring after several decades. I asked the colleague what her plan was for post-Post life. “I don’t know,” she said.

Whether you are 30 or 60, here are some ideas I combined from Fleshner and Robinson for figuring out your next move.

● Get over the ego thing. If you define yourself by what you do professionally, it will be more difficult to switch careers.

● Don’t be afraid.

● If you are quitting for good, have a plan, even if it’s a loose one. Will you travel? Spend more time gardening or bicycling or enjoying a hobby? Take a part-time job? Or spend more time with the grandchildren? If you’re like most people, after you have retired for a while, you start to ask yourself, “How did I do everything I did before retirement?” Because your life is so full.

● Stay connected to people and build in something active to keep your mind and body vital: walking, volunteering, mentoring, eating well, etc.

● Don’t be dumb. It’s important to push beyond your comfort zone but play within your limits. Fleshner was fortunate to have a spouse who was still working and who supported his desire to try something completely different, which turned out to be organizing footraces.

● Whatever you do, don’t sit and rock and wither away. Studies show sitting for long periods of time is the worst thing you can do for your health, as bad as smoking. This is a time in life to get out of your comfort zone — not get into it. Stick your neck out if you want a rich and stimulating retirement. Do things you’ve never done before. Scare yourself. Make mistakes. Refuse to be perfect but insist on being the You you never could be.

Fleshner walked away from his UnitedHealthcare job and eventually started his distance running company, known as RDB Running.

His biggest race, known as the American Odyssey Relay, was a 200-mile overnight relay race that started in Gettysburg and finished in Washington. He organized the races from 2007 to 2017, including every detail, down to the water cups, permits, medals, recruiting volunteers and renting the portable toilets.

The business paid off, netting a five-figure profit on up to $250,000 in gross revenue.

I asked Fleshner whether he ever had any regrets about quitting the executive suite to run his own company organizing races.

He said the only question he couldn’t answer was whether he was any good at it. Then, somebody answered it for him.

“When you are a lawyer, you know you’ve made it when you appear before the U.S. Supreme Court,” he said. “If you are a doctor, you do a big surgery in a major hospital. I was running with a friend near the Bethesda towpath, when a guy who services porta-potties leaned out of his truck and yelled, ‘Hey, Bob! Great to see you!’

“I knew I had made it in the racing world at that point,” he said.

(Photo by Katherine Frey/The Washington Post)