I credit Association X with keeping me from being an early career job hopper. I stayed with that organization for nine years. Under normal circumstances, stability is my vanilla. It would never be my choice—even as a double dip with sprinkles on a waffle cone.

I was the kind of kid who destroyed intricate lego creations as soon as they were completed so that I could start over again. I would have loved to receive the world’s largest jig saw puzzle for Christmas. (This cardboard marvel, currently sold by Hammer and Schlemmer, includes 32,265 pieces, weighs 40 lbs and comes with its own hand truck.) Chaos is just as disturbing to me as it is to the next person, the difference is that I thrive on creating order out of the craziness.

Association X was the Wild West. Work was never dull. There were regular shoot-outs and enough problems to keep a compulsive fixer like me glued to my chair. (I was going to say I was fascinated, but it would be wrong to characterize an addictive experience in such a glowing light.) Five different CEO’s tried to break that bucking bronco, but none fully succeeded. Each new cowboy brought a different posse and rewrote the laws. I really had five jobs, instead of one. That variety put the spice in my life.

It was inevitable that, eventually, I would need to get out of Dodge. I had a young family, and as much as I loved the unrelenting challenge, I understood that a 24/7 adrenaline rush does not make for a healthy lifestyle. I stocked up on pantyhose, sent my navy blue suit to the cleaners and set out to conquer the world. I didn’t really know what to expect. After the first few interviews, I was pleasantly surprised. There were some intriguing offers on the table. I was invited to build the Chicago office for a growing software company, to take the top spot at several social service organizations and to join a large consultancy. But it was a Goldilocks situation. Each tempting choice was slightly askew. One job seemed too limited, another too expansive—nothing fit “just right.”

After several interviews with a well-known medical association, I thought I had found my sweet spot. The job as project manager would keep me busy without leaching into my personal life. My final meeting was with John the COO. John, who is now a good friend, delivered the bad news. He said, “Sherry, within six months you’ll be so bored you’ll hate me for hiring you.” This was the truth that I had been hiding from myself. It was one of those come to Jesus moments. I couldn’t settle for vanilla.

I was at a crossroad. Should I keep looking for the perfect 9-to-5 job that would never make me happy, or should I reinvent myself? When I’m considering a tough decision, I always make a list. Seeing my options laid out in columns is calming and assures me that an answer is just a keystroke away. I made a simple inventory summarizing “What I Love To Do” and “What I Hate To Do.”

Helping people and solving problems came out on top. I realized that the only way to splurge on chocolate fudge without killing myself was to be in control of the situation. To pick my own ice cream, I would need to start my own business. I created a brand, developed a website, printed business cards, and then it was time for the final step, saying goodbye to Association X.

I’m not going to pretend that this was easy. Deliberately turning your back on a reliable salary raises eyebrows, especially among family and friends. You must see yourself as a success before anyone else does and believe wholeheartedly in your vision.

You can’t buy that kind of confidence. You need to become the headhunter from hell. I gave myself an interview to make sure that my qualifications were strong enough to meet the responsibilities ahead. I asked really tough questions. When I was certain that I had made an honest, objective and compelling case to the devil on my shoulder, I took the leap.

I had enough money to go without work for six months. Fortunately, the professional relationships and credibility I had already established, ensured that I was busy almost immediately. I have never regretted my decision to say no to vanilla.

These are some of my favorite strategies for keeping the options flavorful on the job and in life:

• Make yourself strong enough to swim to shore against the waves.
• Discover what people can’t live without, and become its master.
• Help others get to where you would like to be.
• Create a professional safety net—You can’t place a value on your peeps. Force yourself to go to the conference or stay at the reception for longer than 10 minutes. Don’t just meet your colleagues, make them your friends.
• Have courage.
• Bring out the pom poms and cheer yourself ahead.