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How to Decide If You Should Turn Your Hobby into Your Life's Work

A Guide

Thinking about ditching your 9-to-5 to pursue your passion full time? Take this advice into account first. [TWEET]

“I work at a hotel management company, but my true passion is painting. I feel most alive when I create my art, but I am reluctant to pursue it full time for fear of financial instability. I have family responsibilities, and can’t afford to be a starving artist!” – Anna, age 40

“I work in a stable government job, but what I want most is to launch a non-profit that would help underfunded orphanages in third world countries.” – Julie, age 27

“I work for a consulting company. I have this idea for a product that would revolutionize the way we buy things online. My responsibilities at work are keeping me from devoting my time and focus to mapping it out, and my fear of failure paralyzes me. Help!” – Steve, age 29

As an executive coach, every now and again I get a call from someone who is trying to figure out what they want to be when they grow up. Some are excited, some terrified, and all want me to guide them through a decision: keep a day job, or pursue a passion full-time.

As coaches, we are trained to come from the place of possibility. You can be anything you set your mind to! Reach for the stars! Jump and the invisible net will catch you!

That said, I have witnessed circumstances where the net failed, the stars were out of reach, and logistics created very real limitations. While I do want for my clients to honor their values, my belief is that a grounded approach to entrepreneur advice serves them best in the long run. I do not wish to dash their dreams, but to set them up for success and happiness on whatever path they choose.

So without further delay, here is my coach-in-a-box guide with entrepreneur advice for the readers who would like help deciphering whether to turn their hobby into a full-time gig.

Does your hobby or passion reflect one of your deep-seated values?

As Elvis Presley put it, “Values are like fingerprints. Nobody’s are the same, but you leave ‘em all over everything you do.”

Here is another way to think about it: getting your needs met brings you satisfaction, while living a values-oriented life makes you fulfilled and allows you to be the best version of yourself. You might value adventure, mastery, creativity, or contributing. There are good values inventories online that can help you if you struggle to name yours (I found this one with a simple Google search.)

Quest: Name your top values. Is your hobby is aligned with one of them?

Here is a story to illustrate this point: Eric is in his 30’s, a husband and a father to an adorable 9-month-old daughter. Eric is also a CPA; most days, he likes his job as an assistant controller at a medical device company.

If you ever met Eric, you would know immediately that he is passionate about the environment. Eric loves nature: he spends his weekends hiking, camping, and planning the next family road trip. He published a book about the best hiking trails of New Mexico when he was 20. His family makes low-impact, resource-conscious choices about their daily lives. Stewardship and adventure are two of Eric’s values, and his hobby is a reflection of those values.

Should Eric quit his job as a CPA, sell his house, buy an RV, and take a life-long road trip? Let’s look at the next question to sort it out.

Will monetizing your passion compromise what you love about it?

Unless you're independently wealthy (in which case, congratulations!) you will need a way of making money. Hope is not a strategy, so winning the lottery to finance your next move is probably not a viable option. Let us assume that you will make a living working in your area of interest. Will it destroy what you love about your hobby?

I am not just talking about the stress and the pressure that will come from needing to monetize what was primarily a source of fun. You may need to compromise the kind of art that you make, show up earlier than you would like, and do the selling. Does the thought of that drain you?

Quest: Think through the dynamics of getting paid to do what you are passionate about. Will it compromise what you love most about it?

Time for a reality check.

Can you commit to connecting with three people and picking their brain about entrepreneur advice, including what it is like to make a living in the field that calls to you?

I invite you to play an investigative game. It’s time to separate truth from fiction when it comes to your area of interest, and in order to play you will need some allies. The good news is, you know a lot of people, and those people also know a lot of people. Six degrees of separation are about to help you.

Quest: Through your extended network, connect with three individuals who are currently pursing your area of interest as a full time job.

Reach out, ask them for a phone call or offer to buy them a coffee, and put on your detective hat. How did they get where they are today? What advice do they have for someone in your situation? What is the favorite part of their day? What do they dislike about their job? What is the inside reality of their work that an outsider would never get to see? If they had to do this over, what would they do differently?

You may find that people are surprisingly open about their experience, willing to share their passion, and generous with entrepreneur advice. These conversations have the potential to light new pathways and open doors, so jump in and see what shows up.

What would you be giving up in pursuing your hobby full-time?

In the words of Laura Berman Fortgang, a career coach and the author of Now What? fear, doubts, and lack of training are nothing compared to the stopping power that we attribute to money. Often, what ultimately kills the willingness to try something new is not the lack of money, but rather its abundance (“Will I be able to keep my lifestyle?”)

Here is the next puzzle piece, and you probably won’t like it. I want for you to face the money and lifestyle question head on. An opponent in the dark is at least three times as scary, so let us turn some lights on.

Quest: Make a list of things you would have to give up. It won’t be just money, although money is probably a part of it. Write down what you would have to have less of, more of, stop doing, or give up in order to focus on your interest. When you are done, consider the list, and ask yourself if you still want it to be in the forefront of your life.

Example time:

James, a paintball aficionado in his spare time, considered getting a competitive sponsorship to focus on the sport completely. Upon further reflection, he realized that he would have a significant travel commitment for out-of-town games and championships, which would make him an absentee father to his 4-year-old twins, something he could not live with.

Lara, on the other hand, was so passionate about photography that she felt she could live with the loss of a reliable paycheck from her job. She went on to become a full-time photographer, and opened her own studio 3 years ago.

Is your desire to explore a passion, a path or an analogy?

Here is another great question from Fortgang’s work, one I have not seen anywhere else.

Quest: Consider whether this is an actual path you were meant to follow, or an analogy for something in your life that you must transform.

Here is an example:

Allison was a young professional working at a big-name consulting company. She loved what she did, and in the beginning the 100-hour weeks did not bother her, but as the pace became unsustainable, she considered quitting and becoming a yoga instructor. As Allison reflected on her next steps and considered the path vs. analogy question, she realized that her desire to teach yoga was really about wanting more peace in her life – something that her marriage, difficult in the best of times, did not afford her. Her next steps were perhaps even more difficult than simply changing jobs, but she appreciated the clarity that the reflection brought.

If you sense that the desire you feel is an analogy, you could first try to reflect on your current situation and see if you can change it to better align with your values.

The ultimate question is: are you willing to make the sacrifices it would take to do this as your livelihood?

You might discover that you are clear on the path and ready to take on the challenges to turn your hobby into a career. You might find that you would rather stay where you are.

A useful thing to remember is that maintaining status quo and pulling the plug to dedicate yourself to your passion 100% are not your only options. You can consider taking a leave of absence, negotiating a flexible work schedule whereby you can dedicate one full day a week to your interests, telecommuting, or using your stockpiled paid time off to have a stretch of time to focus on your hobby full-time as a test run.

Whatever you decide, this thought process and entrepreneur advice has a lot to offer. If you wake up every morning and yearn to dedicate yourself to your passion, you owe it to yourself to at least consider it.

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Write your resume like a pro.

TopResume's resume worksheet is just like the one our pros use. Download it now for free and start getting more interviews!

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Write your resume like a pro.

TopResume's resume worksheet is just like the one our pros use. Download it now for free and start getting more interviews!