How to Keep Your Dreams <em>and</em> Your Day Job

As much as we'd like to be starting our own businesses, finishing our novels, selling our albums, or getting out to those casting calls, we feel chained to our chairs, shackled to our spreadsheets, drowned in our dead-end day jobs.
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In the struggle to integrate work with a meaningful, fun, and fulfilling life, many of us find our big dreams colliding with our occupational realities. As much as we'd like to be starting our own businesses, finishing our novels, selling our albums, or getting out to those casting calls, we feel chained to our chairs, shackled to our spreadsheets, drowned in our dead-end day jobs.

And the prevailing wisdom is that you just have to quit the job, cut the cord, take the leap from the job that you tolerate to the work that you love. Unfortunately, following that wisdom has led far too many people to financial ruin, frustrated ambitions, and unfulfilled dreams. There's a better way -- and it doesn't involve quitting your day job to chase your dreams.

Don't be a quitter

Jon Acuff's book, Quitter, is filled with wise ideas about why keeping your day job is a better path to achieving your dreams. Here are just some of the reasons Acuff gives for keeping your day job while you pursue your dreams:

  • When you have a day job that meets your financial needs, you have the freedom to pursue only the things that move you closer to your dreams. When you quit your day job, you might have to say "yes" to things that make you money while actually pulling you further off course.
  • When you have a day job that you can contain and control, you have the time to truly plan your strategy, make connections, and lay the groundwork while still making an income.
  • When you have a day job that isn't quite your dream, you have the motivation to hustle in ways that move your dream forward.
From his experience and perspective, the people who build and actually achieve their biggest dreams aren't those that cut the cord rashly and irresponsibility. Instead, they're the ones you have the discipline and determination to use their current situations to support their ambitions. Here are some quotations from
to give you some food for thought:
  • "When you keep your day job, all opportunities become surplus propositions rather than deficit remedies. You only have to take the ones that suit your dream best."
  • "Quitting a job doesn't jump-start a dream because dreams take planning, purpose, and progress to succeed. That stuff has to happen before you quit your day job."
  • "I know it sounds crazy, but people with jobs tend to have more creative freedom than people without."

Finding creative freedom in your day job

At this point, some of you might be thinking, "Yeah, that sounds great, but I have a demanding job that consumes all my energy, time, and resources." Sure. I get it. It is not easy to follow your passion(s) while also fulfilling that dream of having some food in your fridge and the electricity to keep it cold.

On the other hand, many accomplished folks -- and some outright geniuses -- have done exactly that. A little over a year ago, business journalist Lydia Dishman published an article on Fast Company's site called "10 Famous Creative Minds That Didn't Quit Their Day Jobs." Here are some of the highlights:

  • Dustin Hoffman, who started out wanting to be a classical pianist, started acting in his early 20's, but that did not pay the bills. While working as a theater actor before his 1967 breakthrough film role in The Graduate, he also worked as a waiter (of course), a temporary typist (not surprising), a toy demonstrator at Macy's, and an assistant at the New York Psychiatric Institute, where one of his responsibilities was holding patients down while they received shock treatments.
  • Sculptor Richard Serra, composers Philip Glass and Steve Reich, actor/writer Spalding Gray, painter/photographer Chuck Close all worked as furniture movers for Serra's Low Rate Movers company while building their oeuvres and reputations. Glass, who also worked as a plumber and a taxi driver, recalls one of his fares informing him that he shared a name with a very famous composer.
  • Five years after publishing the critically acclaimed Player Piano, writer Kurt Vonnegut opened and managed a Saab dealership on Cape Cod. Unfortunately, the business was a miserable failure. Vonnegut once quipped, "I believe my failure as a dealer so long ago explains what would otherwise remain a deep mystery: why the Swedes have never given me a Nobel Prize for literature." Prior to his misadventures in automotive commerce, Vonnegut worked as a news reporter and as a public relations flack for General Electric.

Of course, this list could go on and on. Jeff Koons was a stockbroker. Mark Rothko taught elementary school. Julian Schnabel was a dishwasher. Keith Haring was a busboy. Patti Smith worked in a used bookstore.

Keep your day job without killing your dreams

So what can you do to keep your day job without killing your dreams? Like all difficult questions, there's no single right answer, and as I've found with my coaching clients, the right solution for you won't be the right solution for anyone else. Nevertheless, here are a few possible strategies to consider when figuring out how to hold onto all the benefits -- tangible and intangible -- of a day job while still making progress toward those big ambitions:

  • Find an intersection between your day job and your dream. That job in the marketing department might seem like a soul-sucking grind, but might there be things you can learn from it that will make your business or your artistic endeavor more successful. On the other hand, is it possible that your experience marketing your band's CDs might actually help your employer be more successful? The ideal arrangement is if your day job somehow feeds into your dream and vice versa. Finding ways to connect the dots between how you make your living and the life you want to make is a strategy that helps many people keep their heads and their hearts while keeping their jobs.
  • Find a job that requires as little energy as possible. For some folks, the best path to pursuing their dreams is the one of least resistance. Philip Glass composed a truly shocking number of works while laboring in furniture moving, taxi driving, and toilet repair. Of this time, he says, "I was careful to take a job that couldn't possibly have any meaning for me." I suspect, however, that the inspiration Glass took from the people he met and experiences he had in these jobs showed up in his compositions in some way -- which brings us to the third strategy.
  • View your day job through the lens of your dream. Day jobs -- especially corporate ones -- get a bad rap for being heartless, faceless vampires that sap your will to live, much less dream. The truth, however, is that a job is a rich sources of experiences. You meet interesting (if sometimes maddening) people. You solve difficult (and ideally worthwhile) problems. You learn useful skills. Any and all of these things might provide inspiration for your art or girders for your business, if you shift your perspective and start looking at your day job differently.
  • Be practical. Many day jobs provide benefits that make dreams more achievable. Obviously, you should be using the money you make to invest in the development of your dream, but there are many other ways to use your day job practically to support your ambitions. If your employer provides tuition reimbursement or other training benefits, use them to build your knowledge, skills, and credentials. If you have access to relevant networking opportunities through your employer, take advantage of them to connect with more like-minded folks. If you have paid time off, use it occasionally to put time into your business.

Keep your head and your heart while keeping your job

Far too much well-meaning advice tells you that, in order to create a meaningful life, you have to ditch the day job dive headlong into your dreams. Unfortunately, dreams rarely come with the safety, security, and stability that good day jobs offer. Comedian and commentator Joe Rogan means well in encouraging people to take the leap, but I question both the wisdom and the confidence of his assertions:

There's no shame in wanting safety, security, and stability. At the same time, it doesn't have to come at the cost of pursuing and achieving your highest ambitions. It is possible to keep your head and your heart -- and your dreams and desires -- while keeping your job. I've watched friends, family, and coaching clients do it, and I've done it myself. Don't buy the all-or-nothing, black-and-white, cut-and-dried perspective that tells you to quit your job. You're smarter than that. And when you take a smart approach to pursuing your passions, you can both do what you love and love what you do.

To achieve all that we were meant to achieve in this life, we must bring our whole selves to work -- and to everything that we do. As Vonnegut wrote in Mother Night, "We are what we pretend to be, so we must be careful about what we pretend to be."

NOTE: After completing this article, I realized that all but one of my celebrity examples were men, and only two of Dishman's 10 were women. I would love to hear some examples of awesome women who achieved great things while holding down a day job. Please add them to the comments below.