Quitting is easy. Starting over is harder.

Seven ways to get a head start on your midlife reinvention. "Look at where you are. Look at where you started."

I saw Hamilton this weekend and am still bouncing around the house, singing snippets of my favorite songs. “Why do you write like you’re running out of time?” IYKYK

I love the Cabinet Battle scene where Alexander is frustrated because he doesn’t have the votes for his financial plan, and President Washington says, “Winning is easy, young man. Governing is harder.”

Isn’t that always the way? Coming up with the idea, taking the leap, slamming the door—a piece of cake once you decide to do it. But then what?

Quitting my job wasn’t hard, but explaining it was.

I’m not retiring! I declared over and over again. At 56, ten years away from social security, I couldn’t bear the word. Also, I knew I would return to some kind of paid endeavor.

In the email announcing my departure, my manager referred to the move as “pivoting,” which I liked a lot. I just didn’t realize how long I’d be twisting on one foot.

In 2021, record numbers of people voluntarily left their jobs, and the trend continues. Some retired, some relocated or changed careers, and some took a break and returned to work. Everyone reconsidered their work-life balance, their goals, and, I hope, their heart.

Quitting isn’t hard, but starting over is complicated.

These five women quit during the great resignation. How are they doing a year later?

• One took a new job because she was running out of money. She doesn’t feel valued, but the thought of leaving makes her “want to throw up.”

• One changed her career and makes much less money, but she’s “never been happier.” 

• One is retired; a former school teacher, she has no regrets.

• One left a toxic employer, couldn’t find a new job, and fell into debt before bouncing back.

• And one is a new mom enjoying time with her son and working part-time.

I quit my job more than a year before the pandemic prompted a surge of work-life reinventions. But if The Cut had interviewed me, here’s what I would have said:

…One year later. I have no idea where the time went. I was having fun, but without the day-to-day structure and validation of working, I lost my compass.

…Two years later. In a lucky (?) coincidence, it turns out a pandemic lockdown was a great time to begin a low-residency MFA program. Connecting to new friends on a common mission to create beautiful words was a life-saver (even over Zoom).

…Three years later. <holds up MFA diploma> <ignores dwindling bank balance>

…Four years later. I am a writer, writing a book. My essays are getting published, and sometimes I get paid for the privilege of doing what I have always wanted to do.

Quitting is the first step. Starting over is a process.

I did not know it would take four years to complete my so-called pivot—five if you include the year I was still working and planning my exit. But I’ve learned a lot along the way.

Seven steps for a starting-over head-start:

1. Reflect. Shift your thinking from job titles, influence, and pay ranges to what makes you whole. When are you happiest? What is the common thread that runs through the work you most enjoy?

2. Plan. Figure out health care and finances. Talk to your partner, your kids, and anyone else who may have expectations about your time or your budget during your pivot.

3. Recharge. Once you’ve jumped, give yourself a break. Commit to nothing for at least six months if you can. Take naps.

4. Connect. Network and build relationships. Find your people and be there for them.

5. Learn the Tech. Goodbye Slack, whee!!! Time to build a new tech stack for what comes next. Stay on top of business, politics, and financial trends. Never say, “Oh, I’m not techy.” I mean it. It’s 2023, for God’s sake.

6. Build an online presence. Instagram doesn’t count unless you’re Selena Gomez. And not even then, really. Find forums where you can engage on a professional, intellectual—and respectful—level. Start with LinkedIn. Contribute insights and support others traveling a similar path.

7. Reignite. Be open to adventures. Be open to what scares you. Set big goals. Establish new habits. Get down to it!

Prompts to reinspire your next chapter

Drop a few lines of writing in the comments, and I’ll share mine too. There is only one rule. Be kind to yourself as you write and to others as they trust us with their words.

Prepare to be interviewed one, two, three, or four years in the future.

• Reflection: If you quit something now, what (and how) would you be doing?

• Inspiration: If you start something new today, what (and how) would you be doing?

Last-to-Know Links

My brilliant friend, writer and career coach Stacy Kim, wrote a piece for WIRED. She thinks binge-watching is better than making New Year’s Resolutions.  Read it to find out why.

I love stories about late bloomers. Being one and all.

Because it’s February and we’re moving into the “still winter” phase of winter. Watch YoY o Ma give a surprise summer concert at Acadia National park.

Gallup created a 12-question quiz to assess your workplace happiness.  My results? 12/12 Strongly Agree!

Finally, some wise words from the Workfriend at the New York Times. Roxane Gay’s insightful take on reflecting on our professional lives. (this is a gift link, no subscription required)

Work hard. Be Brave. Believe.

post cover photo by Tim Mossholder on Unsplash