Late career: Don't overstay your welcome

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REFLECTIONS

Timing your corporate exit

A lot of factors go into deciding when to exit your career. Many of these factors, including financial readiness, are deeply personal. Many people just seem to have an innate sense of when it’s time to exit stage left. Others, however, persist well past their professional expiration date. Let me tell you about a conversation with a man we’ll refer to as George.

George is exhausted

George joined us as part of a three-person field team on a cross-country sales call. Like all of us, George started the morning by checking a few emails before packing his bags and heading to the airport for his flight. When we all met at our arrival airport after a day of travel, George looked like he was ready to fall over. See, George was already well into his 60s, more than twenty years older than the other two team members.

The usual justifications

That evening before dinner, I met up with George for a drink on the hotel patio. Deep lines edged his face and he looked like he’d rather be anyplace but at a business hotel preparing for a team dinner and last-minute presentation refinements. I asked George why he was still working so hard. His first drink response was predictable: I still love what I do, I can’t imagine quitting work, I’d be bored to death if I retired, I don’t like golf…blah, blah, blah.

The truth emerges

But, by drink two, a truer George started to emerge. He and his wife still had a mortgage on their home. (!) Despite downsizing to a smaller townhome, they insisted on remaining in the high cost of living East Coast city where they had raised two daughters. They paid for both daughters to attend prestigious Ivy League schools. (One daughter became a bit actress, the other a homemaker. While homemaker is the most important vocation there is, and bit actress I’m sure is a fine career, neither woman’s career trajectories required an eye-wateringly expensive education.) A few more details spilled out which suggested George and his wife had not lived in a money-wise fashion. They were still in debt, leased brand new cars and had seriously under-invested for retirement.

Considering better options

My heart sank for George. He was exhausted not even 24 hours into a two-day business trip. He was still trying to pull down a hefty salary in a desperate hope to make up for lost time and secure a decent retirement for him and his wife. While I admire the grit it took for this man to wake up each day and compete with people the same age as his kids, all I could think was: Buddy, you’ve seriously overstayed your welcome in this industry. Why don’t you and your wife downsize further so that you can relax a bit? Can’t you go do something else for a living? Could you work at something that doesn’t leave you looking like a desiccated fossil making a sorry attempt at living a younger man’s life?

KEY TAKEAWAY

I hope that anyone reading this has made financial decisions that won’t result in feeling pressured to overstay one’s welcome in a job better suited for you two decades ago. Unfortunately, financial preparedness for retirement is the exception in America, not the rule.

Regardless of where you stand financially in terms of being ready to retire, I want to encourage all late-career professionals to be mindful not to overstay your welcome in corporate America. At a certain point, you owe it to yourself and your household to switch gears, stop pretending to be the younger you and take on a fresh and exciting new job challenge. You really area capable of amazing things, something better and bolder than your corporate job. Besides, nobody stays in corporate America because it’s fun. Everyone knows “the old guy” is still there because he doesn’t have a choice. And that’s not noble or admirable, it’s sad. Don’t be George.

Late career: Don’t overstay your welcome