[Note: This piece was originally published on Matador, where I was managing editor and lead faculty member of the travel writing course. Over the next few months, I'll dust off some other articles from my Matador days that I'll be updating and republishing here.]
Since quitting my 9-to-5 job as the assistant director of a mental health agency in 2004 and becoming a full-time traveler and writer, many people have remarked that they envy my lifestyle. What they don’t recognize is that they can create the same kind of life for themselves by following a relatively simple set of steps, which I’ll share with you here. I didn’t plan the kind of life that I have now—in fact, I didn’t plan at all; I just quit my job without a Plan B, which is not the best idea for most people. My experiences of living on the edge, though, have helped me identify the top 10 tips for you to ditch your own 9-to-5 job and have a bit more security than I did.
1. Let go of your long-cherished vision of your professional self.
When I found myself unexpectedly answering my boss’s question, “How are we going to work together?” by answering, “We’re not, because I quit,” I didn’t realize that one of the biggest challenges ahead of me was letting go of the career trajectory I’d mapped for myself. By the age of 25, I’d been the first poetry therapist to work in two New York City social service agencies, I’d already reached the middle management rung on my profession’s ladder, and I’d simultaneously begun building my own counseling and consulting business with two colleagues. I was published in an academic journal and I was the director of a board. I was well on my way to fulfilling my high school yearbook’s prediction of “Most Likely to Succeed.” Dropping out of the profession meant I’d be disappointing a lot of people—my parents, who had paid for my Masters degree, my mentor, who had nurtured my learning and my career, and myself, as I’d planned big professional accomplishments by the age of 30. In order to ditch your 9-to-5, you’ll need to begin to let go of whatever conventional career plan you had for yourself and whatever expectations everyone has ever had for you.
Practice becoming comfortable with ambiguity and what others might consider to be aimlessness. Don’t underestimate the work this step takes. Our society is largely structured around the maintenance of the 9-to-5 life.
2. Perfect your pitch.
When you’ve made it through step 1 and you’re starting to become comfortable with the idea of the new professional you, one of the next challenges you’ll confront is explaining yourself and justifying your career and lifestyle change to almost everyone you know. Don’t be apologetic for your decision to forgo the traditional trajectory, but do take the time to develop a pitch or a story to tell when someone asks you why and how you’re forging a new path for yourself. A true and well-crafted narrative is compelling to most people—even those who’d like to see you conforming to social expectations—and it can often serve you well. When I explain how I was once a social worker who had her own business and worked as the assistant director of a New York City agency, then owned an art gallery, and then became a full-time writer, editor, and translator, it becomes a hook for continued conversation and often leads to offers of work and further exposure.
3. Make an inventory of your skills.
Whether you take the time to plan your transition or whether you jump into it headlong, as I did, it’s incredibly helpful to make a written inventory of the skills you possess that can bring you work and other opportunities. As I listed my competencies, I realized I had skills and knowledge that were so second nature to me that I hadn’t realized their potential value as sources of work. In this initial list, include everything that comes to mind—don’t censor yourself at all. If you can cook, clean, write, translate, organize, sing, type, take photos, transcribe, surf, do calligraphy, or make movies, write it down. If you’re short on ideas, ask a trusted friend to make a list with you.
4. Narrow the list.
Once you’ve made an inventory of your skills, review it and begin to narrow down your possibilities for independent work. Subject the items on our list to three criteria: (1) Which of the skills are portable? (meaning you can use them anywhere in the world); (2) Which of the skills are profitable? (meaning that they’ll generate income—not enough just to scrape by, but something to actually live on); and (3) Which of the skills have the lowest demand load? (meaning which will not require you to purchase special equipment, obtain employment authorization in another country, secure a work visa, or otherwise require negotiating red tape and the constant monitoring of bureaucratic requirements and deadlines).
5. Rework the list.
Now that you’ve determined which items on your list are most portable, most profitable, and lowest demand, begin to refine the list a bit more. What are the top five skills you could use to seek work that takes you outside of the 9-to-5 grind? Which skills might lead you to actual job leads? How can you generate work using these skills no matter where you go? Which skills will lead to work when you need it?
6. Plan with a partner.
If you’re in a serious long-term relationship, you need to discuss your ideas and plans with your partner. Ditching the security of the 9-to-5 life and trading it in for a life that is more independent and flexible is not for everyone and it requires risks that may not be acceptable for all people. When you are in a relationship, the needs and abilities of your partner with respect to adapting to your plans need to be discussed and agreed upon. What kinds of shifts may need to occur in your day-to-day life in order to make the transition realistic and to what degree is your partner willing and able to accommodate and support you?
7. Assess your security needs.
If you’re the type of person who needs medical and dental insurance, a 401(k), and a steady, predictable paycheck, then you will need to do some serious planning to fulfill these needs before ditching your full-time job. There are resources for meeting these needs off the regular workday clock (see Freelancers Union for some great ideas), but you’ll need to do most—if not all—of the legwork on your own. You’re now the chief, cook, bottle washer, and human resources director.
8. Be for real.
Before you ditch your 9-to-5, do a searching inventory of yourself. The main criterion? Be for real. Are you a person who needs structure? Do you work best with others? Do you have a hard time scheduling, organizing, or delegating your time well? Do you need the praise of a superior or the affirmation of colleagues? Are you envisioning life off the 9-to-5 grid as one long adventurous, romantic narrative? If the answer to any of these questions is “Yes,” it’s likely that you’ll find life off the time clock to be a serious challenge. Among the many people who have commented that they’re envious of what they view as my freestyle life, there are a couple who have acknowledged that they’d never be able to follow in my footsteps because they need a boss, they need the predictability of a regular paycheck, or they need someone to assign tasks to them. I admire these people because they know themselves and make their career and lifestyle decisions realistically according to their own personal and professional needs.
9. Create community.
Working off the clock has many advantages, but it can get lonely at times, especially after the initial thrill of working on your own wears off. Be sure that you’ve made plans for connecting with other people no matter what you’re doing or where you are.
10. Assess your progress.
Every once in awhile, take some time to assess your progress. When I stop to think about how my life has unfolded since turning in my resignation and never turning back, I recognize that I work more now than I ever did, but that I’m also happier than I ever was. I also realize, though, that I need to continue refining my short-and long-term plans in order to maintain my current lifestyle. Since I don’t have a boss to sit down and do an annual performance evaluation with me, I need to do constant evaluation myself and so will you.