Each month "Transitions" profiles an individual who has made significant changes in his or her work life and highlights the techniques used to make the changes.
Katie Tiger, 43
Career transition: From administrator for an investment banking firm to founder of a shirt-making company.
What she used to do: Vice president and corporate operations manager of the Boston investment bank Adams, Harkness & Hill.
What she does now: As president of Kool Kat, owns and operates a maker of custom-tailored Hawaiian shirts.
Making the switch: Surrounded by bolts and swatches of brightly colored fabrics and with her cats George and Roberto at her side it may appear that Tiger has always worked in the low-key environment of her Winthrop home and workshop. But the 43-year old entrepreneur had to pay plenty of dues to get there.
"I would have made so many mistakes just out of college," says Tiger, reflecting on how she would have fared starting her own business when she was young. During her years at Emmanuel College, Tiger gained experience working part time at Saks Fifth Avenue and elsewhere before graduating in 1982 as a music major. Unsure of her next move, she used an employment agency to find work as a secretary at a law firm. That lasted for three years before she landed a job as executive assistant to the chairman and chief financial officer of a manufacturing company, Chelsea Industries Inc.
Tiger stayed there seven years. "I learned a lot about the business world and about customer service," she says, "and I picked up some really good skills."
But when the company went from public to private, relocated the main office, and changed the scope of her job, Tiger started to look around. She was able to land a job with another law firm as secretary to a partner, but within two years she felt she had outgrown the position and needed to move on again.
This time, leveraging her Chelsea Industries experience, she landed a position as executive assistant to the managing director of the Boston office of Baring Asset Management.
"It was exciting, a wonderful job, and my skills from Chelsea Industries had me prepared," Tiger says.
From there, she was recruited by the managing director of another financial firm, Santander Global Advisors, to become the office manager of a new internal start-up.
During this time she worked with the chief operating officer to move the firm into new office space and build it out. She also did some event planning.
But despite its success, the business unit was eventually liquidated by the parent company. Tiger was saddened when it closed down, but she had already secured a new position with the investment bank Adams, Harkness & Hill. She oversaw the research department, including the editorial and customer support staffs.
"I did contract negotiations, troubleshooting, loads of things to make sure everything was running smoothly," Tiger says. But this job, too, was in jeopardy when the company restructured and merged her position into corporate operations.
In the early spring of 2002, about 20 years into the corporate life, Tiger took stock.
"I wasn't excited to get up and go to work in the morning," she recalls. "It wasn't fun, and it wasn't the place for me anymore."
She had also grown weary of the endless, unpredictable corporate shifts.
"I'm basically a happy person," Tiger says, "and I didn't want to become a miserable person just for a paycheck. We spend a lot of time at work, and I wanted to do something I loved. When it got to the point I just hated Sundays because I was dreading Monday, I said, 'I can't live this way anymore.'?"
Fortunately for Tiger, the seeds of doing something she loved had been sown years earlier. She had met her husband-to-be, Ted Tiger, during her time at Baring, and one night, on a stroll through Boston's Chinatown, he spotted a tiger-print fabric in a store window that he thought would make a fabulous Hawaiian shirt.
They bought it, and, drawing on the sewing skills she had learned from her mother, Tiger made the shirt.
"He wore it everywhere," Tiger recalls, and soon she was making shirts for friends as gifts. So many orders came in that she could not keep up, and she found it increasingly difficult to work by day and sew at night. Even when she raised the prices the orders kept coming in. So she stopped making shirts.
"It's hard to turn down a nice big paycheck," says Tiger, of contemplating leaving the corporate world. "And starting your own business is a pretty big limb to walk out on."
But by 2002 that time had come. Over dinner at a friend's house, on a trip to Santa Fe, she declared how miserable she was in her work.
"What do you really want to do?" asked the friend, point-blank. "Make Hawaiian shirts," she replied without hesitation.
The friend, a graphic artist, designed Tiger's business card on a napkin on the spot. (He is still the company's graphic artist.) Bolstered by the positive results of the "mini-market research" from the previous shirt-making stint, in May 2002 Tiger finally decided to go out on her own.
"I made a deal with myself," she says. "I'd give it a year, and if it didn't work out I'd go back into the corporate world. But at least I would have tried." Her husband told her to go for it.
Over three years later, Kool Kat is still a go. Tiger handcrafts three shirts a day, all in response to orders. Last year, Tiger sold 700 shirts and had to hire contract workers at one point to fill a large corporate order. The shirts range in price from $85 to $350.
She does all her marketing through word-of-mouth, direct mail, and the company website, KoolKatFashion.com. She sells all her shirts direct, sometimes through trunk shows. A part-time administrator keeps her database of 4,000 customers up to date, and a bookkeeper keeps the financial side in order.
Her husband, a stockbroker, helps out with business planning and pitches in when it's time to get a large order out the door.
As to her new financial reality, Tiger says, "I can pay the bills, and I am starting to pay down the start-up costs."
Her view of her future?
"I want to be able to pay the bills and enjoy life," she says. "I also want to dress the world in Hawaiian shirts, one person at a time."
Do you have a career transition story you would be willing to share? If so, please let us know at transitions@bostonworks.com. Be sure to include your name, phone number, and e-mail address along with a brief description of your career change.![]()

