How to fail upward and build a career in tough times

Mindy Kalings recent TV series Not Suitable for Work finds humor in the fictional lives of five ambitious young adults stumbling professionally, but the reality isnt so funny. Young adults really are struggling.

As a college teacher and author who has spent 30 years helping students of all ages land jobs and bylines, Ive been asked for advice by many recent graduates pessimistic about this slowed down, historically tough job market. I can relate. Over four decades, I took myriad positions to make money (from waitressing and babysitting to forays into advertising, research, journalism, publishing, film, personal assisting and education). Rejected often early in my career, I still receive more refusals than acceptances. Yet I dont take it personally or let it stop me from failing upward, recalling how my first hardcover was turned down by 30 literary agents and 30 book editors before it sold to Random House, leading to several books with the top publisher.

Of course it wasnt easy being ignored, slighted, fired, laid off, let go, screwed over, criticized for too much experience or not enough. Yet as Stephen Sondheim wrote Im still here, actually earning more income now than before, with more freedom and flexibility. Heres what I recommend.

Embrace the rebuff. After you send out CVs, audition or submit an idea or project, celebrate your effort and bravery. It means you tried, put yourself out there and took a chance. I used to throw rejection parties for my students, where a rejection slip was the admission fee. A bestselling mentor once warned me: If you dont take a risk, youre risking even more.

Write your obituary. Yes, its a morbid exercise, but figuring out exactly how you want to be remembered at the end is the perfect place to begin. In my case, although my conservative Michigan parents prayed Id be a doctor/spouse/parent in the Midwest, I envisioned author and Manhattan in the headline. Applying to NYUs graduate creative writing program and trying to get a job as an editorial assistant at the New Yorker were my first steps. (I was shocked they said yes!)

Prioritize paying bills. Despite lofty goals, theres honor and security in earning any paycheck. Indeed, Jon Hamm was a set dresser for porn films, Nicki Minaj a waitress at Red Lobster, Lucy Liu a scooper at Baskin-Robbins, Harper Lee an airline ticket agent, Harrison Ford a carpenter, John Malkovich a school bus driver, Maya Angelou a streetcar conductor. Long after my books hit bestseller lists and my husband had credits on top TV shows and films, we kept teaching by night because committing to six weekly classroom hours added health insurance and a retirement plan. Its also easier to get a job when you have one, and dual roles can enhance each other.

Diversify. That term often refers to stocks and bonds, but my spouse and I applied it to our careers long before the official gig economy created digital nomads. Even with a good position, you cant predict the future (as laid-off friends in the tech world can attest). One year we listed 23 sources of income on our taxes. So if 10 employers went bankrupt, out of business or dumped us, our bills were covered. For her prescient book One Person/Multiple Careers: A New Model for Work/Life Success, Marci Alboher interviewed Francisco Franklin (a techie/pastry chef), Sanjay Gupta (a neurosurgeon/CNN correspondent), Angela Williams (a lawyer/Baptist minister), Carrie Lane (an art consultant/Pilates instructor) and Oscar Smith (a police officer/personal trainer). Expand your mind, portfolio and potential by adding a slash to your own description.

Reduce bad habits. You might only smoke, vape, toke or imbibe after hours, but unhealthy patterns seep into your work and soul. I personally found that my dependence on cigarettes, alcohol and cannabis hurt my sleep, sucked up my best energy and affected my mood, vocation and reputation. Its no coincidence the year I quit smoking, drinking and pot, I tripled my income.

Stay skeptical of all employment. A corporation will always choose its profit margins over your safety and satisfaction. Its a tough lesson well chronicled by my former student Emi Neitfeld, who wrote of being harassed by a superior at Google. Despite an impressive title and salary, you can still end up badly treated, fired or replaced. Many CEOs and founders were ousted from their own businesses, like Steve Jobs (Apple) Whitney Wolfe Herd (Tinder/Bumble), Sam Altman (OpenAI), April Koh (Spring Health), Jack Dorsey (Twitter) and Jerry Yang (Yahoo). Even with secure occupations, keep your eyes open for new opportunities to protect yourself. Cultural commentator Erica Williams Simon advises Dont ever attach yourself to a person, a place, a company, an organization or a project. Attach yourself to a mission, a calling, a purpose only. Thats how you keep your power and your peace.

Consider therapy. Knowing who you are and your weaknesses can be a superpower. And having someone in your corner to share insights is invaluable.

Guard your time and money. After complaining to that therapist I wasnt making progress with my goal of becoming an author, they asked what I did the night before. Id dined with college MBA buddies uptown, costing me $63 though I just had a salad and diet soda, leaving me resentful. You could have gone to a free reading or literary panel, I was told. Hang out with people you want to be.

Welcome reinvention. After losing a job, column or steady work, Id mourn and then rejigger my menu of skills and services and try again. When I was let go from a job at a university after 25 years during the pandemic, I launched my own Zoom classes. Surprisingly I wound up earning seven times my old salary. That gave me the financial leeway to offer scholarships to low-income pupils who couldnt afford to take my classes (unlike my old school, which would chastise me for letting anyone not officially enrolled into each class). Now each term my students brave debuts in newspapers, magazines and books inspire me. Ive felt blessed and beyond proud, multi-missioning so I might help a younger generation by transforming my past mistakes into hope.

Susan Shapiro is author of many books her family hates, including the memoirs The Forgiveness Tour, Five Men Who Broke My Heart (recently optioned for a movie) and the writing guide Byline Bible. Instagram: @profsue123