It may sound implausible—if not downright impossible—but I have worked as a death penalty attorney, a baker, a documentary filmmaker, an award-winning landscape designer, a nonprofit director, and a career and business strategist.

Six wildly different careers. Six different chapters of my life. I loved each and every job—and each one was “right” for me at that precise point in my story. Even more crazy than that is that fact that I never would’ve predicted that I’d be able to turn so many of my passions into profitable jobs. But I’m living proof that where there’s a will, there’s a way, and where there’s a way, there’s a paycheck.

So, how can you do the same? Take these four steps, and you’ll be on your way to living out your wildest dreams.


Step 1: Look for the “Bright Spots” in Your Life

Pay attention to “bright spots” in your day. What are you obsessed with? What do you look forward to? Whatever it is—fitness, baking, snuggling—make note of it, no matter how small or insignificant it may seem. (This worksheet from bestselling author and entrepreneur Danielle LaPorte is a great resource if you’re having trouble getting started.)


Step 2: Dream Crazily

Ask yourself, “If [bright spot] was my new career, what would that look like?” Allow your mind to run wild.

Do you want to become a professional cuddler? (Yes, it’s a real job!) Write about coffee for other caffeine fanatics? Play charming music that delights people?

Make a list of three to five “bright spot” jobs that appeal to you, no matter how far-fetched they seem. Sometimes it is the most unlikely things that eventually blossom into your new career. (And even if the first thing you write down isn’t an option, it could lead to something more realistic.)

Look at my career. After working as a death penalty attorney for many years, I started to crave a break from my intense, emotional job. I had always liked gardening—my favorite form of relaxation—but never thought of it as anything more than a hobby.

Until I read an article about a public school that created a garden to help the kids learn about science in a hands-on capacity. I thought, “That is the coolest thing ever.” I went to a workshop that very weekend, and before I knew it, I became obsessed with school gardens. I called up my son’s school and said, “I’d like to build a garden.” They said, “Sure!” That project eventually unfolded into a nonprofit eco-sanctuary that I raised millions to fund and direct for over 12 years.

You never know where one “crazy dream” might lead.


Step 3: Learn the Required Skills

To transition into a new career, you’re going to need to brush up on your skills. That’s almost inevitable. While the idea of learning something new can feel scary at first, it’s much more approachable once you’ve identified your target job and its required skill set. (To learn what skills you’ll need, look at relevant listings and see what they require to apply.)

Companies like General Assembly, Skillshare, Udemy, and Coursera are all great resources when it comes to picking up new skills. Or consider attending free events and lectures in your community. Anything you do that furthers your ability to do your dream career will get you one stop closer. Especially when you get to step four.


Step 4: Reach Out to People Who Have Your “Bright Spot” Careers

Take the time to do a little research and find people who have your “bright spot” careers (or something similar). Reach out via Twitter or LinkedIn and set up an informational interview. (Nervous to just reach out? Check out these LinkedIn templates). Don’t be scared to talk to friends and family and ask, “Do you know anybody who does [your bright spot career] for a living?” They might say no, but it never hurts to ask.

When you reach out to your “bright spot” contenders, don’t just invite them out for coffee. That’s boring. Be bolder. Instead, ask if you can help them.

Say: “I’m interested in learning more about [industry]. I’d like to help you at work by [describe what you could do to make their life easier].”

You might be surprised by often people say, “Sure!”

Even if they don’t need an intern or assistant right now, there may be an opportunity to partner up on an interesting project that feels like a win for both of you!

Just last year, while attending a blogging seminar, I walked up to thank one of the instructors, Gala Darling, at the end of the event. She asked me about my current projects, and I told her I wanted to develop an online training program for people who feel stuck in dead-end jobs and want more out of life. She said, “Have you thought about partnering with a successful blogger? Someone who could help you to reach a bigger audience of potential customers?” I said, “How about you? Let’s work together!” She said, “I’d love to!”

Our first program just launched, and we enrolled close to 300 amazing students. A huge success—for both of us!


There is a lot of brilliant advice out there on how to craft a stellar resume, write a cover letter that leaves hiring managers breathless with delight, and network like a master. All of that stuff is important, for sure. But even more important than that is finding a career that makes you happy—and, if desired—finding it over and over again throughout your life.

Photo of sunlit fingers courtesy of Shutterstock.