An Interview with Jonathan Fields, Career Renegade

Jonathan FieldsJonathan Fields is obsessed with the process of creation. Over the last decade, he’s created, built and sold two companies, helped launch nearly a dozen brands, launched the popular blogs Awake@TheWheel and Career Renegade and, in January, published the book, Career Renegade: How to Make a Great Living Doing What You Love under Random House’ Broadway Books. Occasionally, he sleeps.

1. What Is a Career Renegade?

A Career Renegade is someone who makes a conscious choice to build your career around the activities, settings and people who make you come alive… and figure out how to do all this while earning enough to live very comfortably in the world and giving back to the greater community.

But, let me make this easier. I make my daughter breakfast, braid her hair, drop her at school, workout with my wife and pick up my daughter after school a good chunk of the week. I work where and when I want, take on only the clients whose vision, products, services and culture jazz me, launch the ventures that inspire me and partner with people to change the world. I work hard, damn hard. I make missteps and mistakes and occasionally crash and burn.

But, in the grander scheme, I love what I do, build it around the people who mean most and make sure that, in the end, the payback is worth the investment… because that’s what makes me come alive.

2. There are plenty of self-help gurus out there telling people to follow their heart — and plenty of business gurus telling them how to get rich. Aren’t you being a little ambitious telling them to do both at once?

First, I’m not about self-help. And I’m not in any way, shape or form a guru, master, wizard or other form of magical obstacle-clearing visionary. I’m about hard work, relentless creativity and nuts and bolts entrepreneurship with a strong bent for marketing.

Now, back to your question. Is it “ambitious” to pursue passion and prosperity together? Hell, yes! But, that’s not the right question.

The right question is… is it worth it?

And, to answer that, you need to do a teeny bit of math (yeah, even creatives can add!). Because, we’re talking about what you are likely going to do with 50-70% of your waking hours for a solid 50 years of your life. That’s 10 hours a day, 5 days a week for 50 years. Translation–112,500 hours of your life. So, seriously, how can you justify NOT striving for both when you now know what’s at stake?

Maybe you’ll succeed, maybe you’ll fail. But, the greatest tragedy lies in the unwillingness to muster the will to try. Helen Keller said it best, “life is a daring adventure, or nothing.” Is that ambitious? Yes. But, it’s worth it.

Also, I’m not about getting rich. To me, that’s a meaningless metric. Money is important, I need to earn 6-figures to live well with my family in NYC. But, in a vacuum, money has no value. It’s only what it allows you to do that has meaning. So, you could spend every waking moment frantically engaged in the mad dash for cash without reference to passion, fulfillment or enjoyment, but to what end? Yeah, you’ll die with a kick-ass estate, but who cares? Your life just sucked.

So, yes, it’s important that you couple the quest to come alive at work with the quest to earn enough. But, the right metric isn’t enough to be “rich,” it’s enough to live well in the world. That number will change radically with each person. And, likely, will change fairly dramatically for each individual over the course of your life.

3. How can you tell if your passion has the potential to earn you a living? Are there some passions that will simply never make any money?

I’m the Career Renegade, so I’m not supposed to say this, but, sure, there are very likely certain passions that will never earn you enough to live well in the world. The number, though, is way smaller than you think because so many people give up the quest far too easily. They just accept conventional wisdom and shelve their passion or turn it into a hobby when an easy mainstream path to prosperity isn’t laid at their feet. Bad move.

Career RenegadeKick the tires. All too often, conventional wisdom is just the collective limitations of those who’ve tried and failed before or, worse, never bothered trying. When someone says, “you can’t do that,” what they are really saying is, “I can’t figure out how to do that, so who the hell are you to try?” Do NOT accept someone else’s limitations as your own without first doing everything possible to succeed on your own terms.

And, that includes looking at the activity that people say “won’t earn enough” in unconventional ways. Mine the broader culture that surrounds your passion. Find and exploit gaps in information, education, community, service, products and mode of access. In my book, Career Renegade, I lay out each of these paths in detail.

Then, take your list of potential mainstream and renegade paths to prosperity and tap the wealth of free, simple to use online tools to determine if there’s a big and hungry enough market of people who want to buy what you want to sell. Use Google’s search, trends, insights and external keyword tools.

Check out for better categorized searches. Use, and to research top search engine listings and front-page advertisers. Check,, and others to discover the intersection between your passion and what people are talking about. These are just a few methods that help ensure you’re going down a path that offers the potential for both passion and prosperity.

4. You make the point that recent developments on the Internet mean that tools and business opportunities are now available that weren’t there even five years ago. Has this changed the game completely, or are the basic challenges facing entrepreneurs the same as always?

It has changed the game in a substantial way… if you know it exists.

You can now research, launch and grow a business in a stunningly short period of time, with very little money and very little risk. And, you can leverage the social web to build a reputation as a thought leader, grow a tightly-woven community, deliver value to that community, ask what need they have that’s not being offered, then deliver a solution with precision to people who know, like and trust you and are waiting for you to help.

If you get that, if you tap that, the web becomes your playground and opens up a far lower risk, incrementally faster path to entrepreneurship and success. Does that mean you’ll succeed every time? Not a chance. But, the cost to try allows you to try far more often and increase your likelihood of success with each attempt.

Even if you’re drawn to brick and mortar entrepreneurship, these same elements can greatly facilitate and reduce the cost of research, marketing and delivery if you’re willing to take the time to learn how to use the tools and operate within the “unspoken” rules that guide much conversation across the social web. In fact, I recently posted about a neighborhood pizza place, Naked Pizza, in New Orleans, that now gets anywhere from 20% to 69% of its day-to-day revenue from twitter.

5. Many people say success requires a lot of hard work, while some Internet marketers are selling the dream of “earning money while you sleep.” Which is the more realistic (and desirable) in your view?

I’ve yet to meet the person who succeeded on any substantial level that didn’t work hard. Can you set up projects that generate “passive” income? Sure. But, truth is, they almost always require huge investments of time and sometimes money to get them going, they eventually burn out and a good percentage of them fail or squeak by. So, it’s important to understand the difference between a product or project, which is what most single info-products are, and a business.

To me, the greater challenge is to make what you work at so rewarding that you have to remind yourself to pull back from it to allow time to enjoy the other people and activities that make you come alive. Work, done right, is good.

6. How do you decide what to do each day? Can you describe a typical working day?

LOL, typical is not a word that’s in my dictionary. I start out very early, usually around 5:30am with personal enrichment time. That usually includes a bit of meditation and then reading or listening to podcasts. I am possessed with the process of creation, persuasion and marketing, so I spend a lot of time studying them.

Then, my daughter usually wakes up next, wanders out to the patio where I often sit to watch the sunrise, snuggles into my lap and we just hang out and watch the morning come in, before getting the day gets started. I spend a while playing with her and my wife, then, from that moment on, every day brings something different.

I often blog in the morning. Or, if I’m working on a book, I write pages. I try to batch my social media time, so I’ll jump on for about 20 minutes early, then again early afternoon, then later in the day in bursts.

And, I often schedule time to work on my own entrepreneurial ventures, joint ventures, work with Renegade Catalyst 1-2-1 consulting and mastermind clients or write copy for clients in the afternoons.

Some days, I pick up my daughter from school or camp, I often break to have lunch with my wife or take a walk in the woods later in the afternoon. Those walks are very often when my best ideas come. For anyone creative, I can’t imagine being able to function with building enough space into each day for that magical, subconscious process to unfold.

One other thing I’ve discovered this year, though, is that with the sale of my last business, the launch of a new book, brand and consulting arm and more ventures coming soon, developing more systems is a necessary part of my ability to stay productive. So, I’ve been focusing a lot on that lately, too.

7. What would you say to someone who’s reading this and thinking “I’d love to strike out on my own and follow my dream, but with the economy the way it is right now, I think I’ll hang onto my job and ride out the storm?”

If you’re living hand to mouth or you need to support a family, riding out the storm may be what you need to do. But, often times, as was the case with many of people I interviewed for my last book, you can find the time to begin to explore, research and build your next great adventure, your renegade career on the side.

Swap TV and Facebook time for renegade quest time an hour a day and you’ll be amazed at what you can accomplish. People often tell me they “need” that time to wind down. Not true. If you want to wind down, work out, meditate or play with your family. Passive screen time is useless time. You’ll find that the moment you begin to fill that time with the pursuit of something passion-driven, you’ll discover wellsprings of energy you never knew existed.

Last thought on this, because so many others are gun shy of entrepreneurship right now, the field of competitors has been vastly narrowed, leaving those who are willing to give it a go with far fewer battles to fight. Warren Buffet recently said in the 2009 Berkshire annual letter (with regard to one of their holdings, GEICO), that he and the CEO feel like “two mosquitoes in a nudist colony” when they look at the opportunities all around them. They’re there, your job is to find or create them.

And, one last thing. If you’re hanging onto your job because you think it’s that “safe” option… read this now.

Jonathan Fields is… a giddy dad, husband, New Yorker, multi-time health & fitness industry entrepreneur, recovering S.E.C./mega-firm hedge-fund lawyer, slightly-warped, unusually-stretchy, spiritually-inclined, obsessed with creation, direct-response copywriter, small-biz and online marketing-maven, speaker, entrepreneur-coach, yoga-teacher, columnist, author, once-a-decade hook-rug savant, pro-blogger and career renegade… gone wild. Read more about his book Career Renegade, work with Jonathan, or follow Jonathan on Twitter

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Responses to this Post


  1. WWoWW! That’s a double wow.

    I’ve always admired Jonathan’s drive to passion and excellence, and I love how he makes that commitment without sacrificing family time or time with his daughter.

    Excellent interview and answers!

    Off to re-tweet this!

  2. Brilliant insights here! What I’ve noticed in dealing with several people in pursuit of “non-traditional” career paths (i.e. doing what they love for a living) is that one of the top reasons why they give up is because they allow fears to take the wheel. Even with invaluable information and innate creative genius at their disposal, they can collapse under emotional pressure. The fears are usually born from hearing so-called “conventional wisdom” from external sources as talked about in the post. The key is appropriately dealing with feelings and emotions that are guaranteed to get stirred up when following your dreams. Take care of them, utilize your resources, and the probability of success is actually great.

  3. Jonathan, you might not be a guru, but you ARE a leader of the highest order. The old rules don’t matter. They’ve all been shattered. Still, the common denominator is there. Even on an entirely different playing field, it is still hard work that fills the coffers. For any creative person who values their time, yours is a model to follow (loosely of course, as all models are meant to be broken. : > ))

  4. @ Brian PAPA – Thanks for the kind words. One of the rules I live by is “your legacy starts at home.” Plus, I just love hanging around my daughter while she’s still young enough not to realize what a serious dork her dad really is, lol!

    @ Craig – No doubt, fear is always a huge issue. But, interesting enough, I sometimes think inertia is the bigger challenge. People just become so comfortable in their routines, it often takes something massive to interrupt a pattern that’s been followed for decades and become open to the possibility of creating a new one.

    @ Writer Dad – Actually, these days, I leaning toward the title, “Official Sponge!” Loving spending a lot of time learning from people who are so much smarter than me.

  5. @Jonathan

    Great point. Would you say that inertia is the bigger hurdle prior to starting a venture? In my experience, it takes facing that particular challenge to even get the ball rolling. The fear usually creeps in more heavily after engagement (the “Oh God, what did I get myself into?” mindset).

  6. Very enlightening-thank you! Betty

  7. @ Craig – It’s different for each person and often depends on how far into life you are, who’s depending on you and how much skin you’ve got in the game.

  8. Great interview. The problems I’m dealing with now are not so much taking action, but finding which actions are the most productive. You hit a point where some projects sound great, but just aren’t worth the time, while others you didn’t think would work are kicking ass.

    It can be hard to find a rhythm in phases like that.

  9. @ Nathan – Indeed, that’s one of the great challenges in keeping the momentum going when you’ve got multiple interests and passions. I’ve found it helps to move the ball forward on a few fronts until you have enough information to determine which one has the least likely opportunity for passion-driven prosperity, then putting that one aside. Then, rinse and repeat.

    The challenge with that is that when you’re trying to keep 5 balls in the air at once, you risk dropping them all. So, if you feel that happening, I’d just pick the one that feels most intuitively right, shelve the others and give that one everything you’ve got

  10. Convention wisdom can get in the way of your dreams, but I agree with Nathan. It can be tiring taking action that gets you nowhere. Sometimes you need someone to take you by the hand.