Ellen was an extremely successful investment banker in her mid 40s who just received a 7-figure bonus. We met each other at the same holiday party at a rooftop bar in Manhattan. And she was very drunk. She slowly rocked forward and backward on her heels and spoke too loudly. It had been eight years since I quit my last job on Wall Street. I meet lots of people like Ellen during the Holiday season.

After a few minutes of sharing her triumphs she asked, “How about you?”

“Oh, I quit my last job on Wall Street in 2015. Honestly, everyone else at this party will make you more money than I will. I’m not looking to sell my startup. I won’t be offended if you want to schmooze with someone more important.”

“Wait. What did you just say?” She was suddenly alert and attentive.

“That I’m not selling my startup?”

“No, that you quit your Wall Street job.” she was whispering now. 

“Yeah. I quit in 2015.”

“Like, you just left?”

“Yes.”

“How? I have three homes, three kids, and I support my brother. This is not a life you just leave.” 

Ellen changed from alpha and invincible to stuck and lost. She gave me a huge hug and said, “Take me with you.”

Unlike Ellen, I lived within my means when I worked in finance. I took the subway, shopped at Costco, and drove a Toyota. And when I realized my job was making me hate my life, I quit and eventually launched Punks & Pinstripes, the executive community that I continue to build and love.

December is the season of holiday parties and performance reviews. I meet a lot of “Ellens” each December. Executives who know they need to change reach out for coaching and advice.

Because when your boss slides the envelope across the table, you invariably think to yourself, “Life is short. Should I spend it here?”

The right move depends on the situation. Broadly speaking here are the scenarios. 

1. Let’s Stay Together. This is the easiest one. You love your job, your company loves you, and there’s room for improvement. There are ways that you can push for progress in your career and your company. But you’re in the right place. Yes, you need to work on the relationship. All great relationships need work.

2. The Anti-Climax. In this scenario your boss takes you out for lunch, buys a bottle of champagne, tells you you’ve gotten a huge promotion, and you immediately want to leave. Who you want to become is not who they want you to be. If you stay, it needs to be with a clear and explicit strategy of what will need to change, and how soon. If you leave, it needs to be with complete support, and potentially with your current employer as a partner, investor, or anchor client. 

3. The Power Situp. The power situp is an evil prank in which someone accepts the challenge of doing a blindfolded situp and unwittingly slams their face into a board, or someone’s backside. The professional power situp is when you have a bad annual review and everything they are asking you to do to improve will make you less valuable, fulfilled, intelligent, and competitive. Your only value to the company is to massage the ego of some political animal. The only good reason to stay in a Power Situp is if the money and benefits are indispensable. The other good reason is that you might be the narcissist, and you’d benefit from deflating your ego and learning. Power situps are rampant in companies that are old, bloated, and bureaucratic.

4. Conversion Therapy. This is when you’ve experienced the power situp and decide to stay and reform. You do everything you can to build trust, be effective, and be kind. You work longer hours. You may realize that the reason you were performing badly was you - not them. And you may become a better version of yourself by performing on their terms. Not always. But sometimes. In my experience, the people who successfully undergo conversion therapy experience a soul-crushing anti-climax afterward.

You are Not Alone

Whichever scenario rings true for you, the most important thing to know is that you are not alone. There are people who have been through the same thing, who can help you connect with your sense of purpose, and help you take the next right action. This, above all, is where the hard work of reinvention begins.

Please, help yourself
- Check out my recent article in HBR, How Banks Stay Resilient as AI Becomes More Disruptive, written with Janene Jonas
- The application window to be one of next 25 members of Punks & Pinstripes is January 15-26. Learn more here.
- Sign up for our FREE 7-Day course on Mastering the Laws of Power In Big Companies