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Do the “Side Hustle” for Your Next Job

What used to be considered pastimes or hobbies might eventually provide your next paycheck.

(originally published by Booz & Company)

This article was originally published by Booz & Company

Last week, a friend of mine quit her job without having another one lined up. (And she’s not independently wealthy; like most of us, she needs to work.) On the surface, her actions appear impetuous. But a deeper look reveals careful planning. For the past 18 months, Julia (not her real name) has been working two jobs: a day job and a “side hustle.” 

A “side hustle” (a term founded in the African-American culture and used by Pamela Slim, blogger and author of the book Body of Work) is “a tiny, independent venture you do during your free time when you’re not at your full-time job.” Side hustles are a form of career insurance, providing supplemental income or serving as a useful fallback in case of a layoff. But a side hustle can also serve as a career accelerator, allowing one to build skills, form important relationships, and develop new business ideas. Today, Slim says, we are best served by considering ourselves self-employed, viewing our employers as clients, and approaching the side hustle as a way to lay the groundwork for a future job.

In Julia’s case, she has been hustling as an author. The process of writing a book has opened doors, strengthened her network, and reaffirmed her passion. And ultimately, the value of her side hustle will extend far beyond the royalties. As the release of her book approaches, she quit her job to dedicate herself to promoting it and using it as a platform to find her next gig.

We are best served by considering ourselves self-employed, viewing our employers as clients.

Slim’s book includes the side hustle as one of eight skills necessary to control “your career in a work environment that no longer has any predictable career paths.” If you want to hustle, she says, select work you enjoy and are good at that has a clear target market and provides the opportunity to “generate a decent amount of quick cash in a short period of time” without breaking any laws. When I recently interviewed Slim, she cited several examples: a marketing executive providing marketing consulting, a technologist developing apps on the side, and a former entertainment executive working on a software startup. Other examples of side hustles listed in her book include include web design, home organization, writing and editing, computer maintenance, massage, tax preparation, yoga, catering, and photography. 

In her blog, Escape From Cubicle Nation, Slim highlights the (often tough) realities of side hustle by sharing others’ experiences and the lessons they’ve learned. Here are a few recommendations I’ve gleaned from reading her posts:

Determine if your side hustle violates your employment contract or policies. If you need to gain approval or believe that what you’re doing will eventually become public, articulate the benefits to your employer or consider if it’s possible to eliminate the conflict of interest by providing services at no cost, at least in the early stages.

Treat your side hustle like a business from the start with an eye toward eventually monetizing your services. You don’t want to be a few years down the road wishing that you had invested in branding and an Internet presence, for example.

Prepare to run a “marathon and not a sprint” by investing two to three years working on both your day job and your side hustle. Working two jobs means long hours and a lot of sacrifices. One idea, says former attorney Laurie Gay, is to switch “to a less demanding job” as “a more regular schedule would have permitted me to do more to get the ball rolling” sooner.

Keep your day job as long as possible and quit when you can no longer handle the exhaustion and anticipation. At some point, juggling two jobs will be untenable, and the opportunity to realize your dream will be impossible to resist. Many side hustlers who Slim has interviewed shared similar feelings that the fear of “never knowing how much I can truly accomplish in life” was far scarier than walking away from a steady paycheck. 

Reduce your risk by planning for your transition. Get your financials in order by downsizing your lifestyle, securing necessary working capital, and identifying a “backup plan,” such as freelancing, to earn extra money during tight times. In addition, consider taking a leave of absence to prepare for the exit. According to Gay, “The more you can immerse yourself in your side hustle before quitting, the better off you’re going to be when you leave your job.”

Few people have the courage or financial cushion to walk away from their current job before they have a new one. The side hustle isn’t for everyone, but it can be a powerful way for passionate, disciplined, entrepreneurial, and hard-working people to control their careers. Every person Slim interviewed was glad they pursued their side hustle. In the words of artist and print entrepreneur Eleanor Mayrhofer, “Now I am either totally jazzed, completely freaked out, super optimistic, or in a funk because of a sales slump, but I never question what I am doing with my time or my life. It’s a wild ride, but I have never felt so alive and on the right path as I do right now.”

Over time, our dreams and capabilities evolve and mature. As a result, we are always one job behind the one we are ready to have. Rather than wish or wait for your next opportunity, consider whether you have what it takes to create your next job while you are working your current one. If you do, it’s time to start hustling.

We are always one job behind the one we are ready to have.


Susan Cramm

Susan Cramm, leadership coach, author, and former CFO and CIO, is committed to the principle that the best leaders take care of business by taking care of the people entrusted to their care.


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