From Wall Street to Wrenches: How a 59-Year-Old Rebuilt His Life as a Handyman
After a corporate layoff, Bob Major found purpose—and profit—through self-employment
When Bob Major was laid off at age 59 from his long-standing role in financial services, he faced the grim reality that many older professionals know too well: finding a new job after 50 isn’t easy.
His entire department had been shuttered, and despite turning to platforms like LinkedIn and Facebook—tools he’d never used before—job leads were scarce.
But unlike some, Bob wasn’t ready to retire. He had seen others do so too early, only to lose their sense of direction or identity.
“I didn’t want to be a shadow of who I used to be,” Bob said.
Instead, he found another path: he launched his own handyman business—and turned what could have been a dead end into a second act.
Starting From Scratch—with a Toilet Seat Job
Bob didn’t waste time. In May 2019, less than a year after his layoff, he applied for a $100 contractor’s license, got liability insurance, formed an LLC, and set up shop as a local handyman.
His first gig? Changing a toilet seat for $35. The customer gave him a glowing review for being polite and personable.
“The next day, the phone started ringing.”
Soon, Bob was installing TVs, trampolines, shelves, and mailboxes—sometimes tackling five or six jobs a day, six days a week.
Charging Too Little—and Learning Fast
Early on, Bob struggled with pricing.
“I wasn’t coming home with much money in my pocket,” he recalled.
After researching local rates, he adjusted his pricing and began earning a fair income. But for Bob, the job was about more than just money.
“I love helping people—many just don’t have time or don’t know how.”
Why Customers Keep Calling Bob
What sets Bob apart from other contractors isn’t just his tool belt—it’s his customer service.
“Clients tell me they’re shocked I even call them back,” he said.
Many of his clients had struggled to get quotes, responses, or follow-ups from other contractors. Bob, who once spent three hours commuting daily to New York City, now keeps jobs local and personal.
Finding Work-Life Balance in His 60s
Now 66 years old, Bob has scaled back. He works four days a week, giving him time to relax with his wife while still earning and staying active.
He has no plans to expand or retire yet. For him, the business is the plan.
“Being your own boss in your 60s is not only possible—it’s powerful.”
Why Entrepreneurship Makes Sense for Older Workers
Bob knows his story isn’t unique. As he puts it:
“As we age, we become more expendable. We cost more than younger workers and are at the mercy of corporations.”
For those like him—experienced but overlooked—entrepreneurship offers freedom, purpose, and dignity.
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