Changing careers can be intimidatingly risky. Fears of starting all over can seem insurmountable, especially if you’ve got job security and a good salary. But at some point, job fulfillment trumps outward measures of success: An unsatisfying career isn’t sustainable if going to work every day seems like a chore.

If you feel like you’re in the wrong career, you’re not alone. Most people make career decisions without knowing what types of jobs might be most fulfilling. And in today’s quickly changing economy, career choices that made sense ten years ago may no longer seem like the right fit. We spoke with three people who have found happiness in second (or third!) careers to get insight into making the big leap successfully.


“You have to be able to tell a story about how much you’d love to work in your chosen career.”

John, 28
Moved from finance at GM to web guru at Hulu

John was the envy of many who graduated at the start of the Great Recession. He scored a job in the finance department of General Motors in 2008 and was initially thrilled to work for one of the largest corporations in America, especially at a time when it was going through serious financial difficulties. Despite the prestige of the job—and risks that came with leaving—he found that finance work wasn’t his passion, and he left to pursue web-based technology. He now works at Hulu in web analytics and user engagement.

What made you confident that you wanted a career change?
I felt that my career had become stagnant—I wasn’t learning anything new or interesting. Once I started immersing myself in web-based technology and coursework, I became certain that finance was not the career I wanted to pursue. But I still didn’t know exactly what I wanted to do. I continued taking classes until I was able to set a real career goal, which I ended up discovering was product management.

What were some of the biggest challenges you faced?
Uncertainty was definitely my biggest challenge. I knew I wanted to go into the technology field, but I had no idea what I wanted to do once I got there. I decided to take a year off between jobs to focus on building the skills necessary. I also attended networking events to make connections and find out about job openings. I actually ended up finding and applying for the role at Hulu through an online job board.

What did you do to find success in your new career?
I worked hard to gain new skills. After leaving GM, I took courses in coding, analytics and product management. This did two things: It helped me prepare for the career switch, and it showed employers I was committed to the switch. After I was hired at Hulu, I talked to some of my interviewers, and one thing that set me apart from the competition was that I had taken the initiative to teach myself things like SQL, front-end coding, etc.

What advice would you give to others considering a career change?
Be proactive and show that you’re determined through your actions. Don’t be afraid to take time to learn new skills that you can tie back into your resume. Employers will appreciate your initiative and dedication to your new career choice. To get your dream job, you have to be able to tell a story about how much you would love to work in your chosen career by showing you’ve taken steps to educate yourself in that career.



“If you have a great idea, go monetize it first.”

Jay, 46
Was a lawyer; now a composer/lyricist and social-media consultant

Jay was a successful litigation attorney who did everything right: He went to a top school, worked hard and developed a reputation for being a smart and skilled lawyer. But he wanted more. In the middle of his career—at age 38—Jay gave up his full-time job and moved from the West Coast to New York to pursue his passion for writing music and lyrics. Success followed: He recently developed an award-winning musical called Allegiance, started his own social-media consulting business, and still practices law part-time.

What made you confident that you wanted a career change?
I was trying to develop a musical at the same time I was trying a case down in Los Angeles. I would often fly down in the early morning, show up at court, file papers relevant for the day, fly back on an afternoon flight, and be at rehearsal in the evening until 11pm. It was crazy, and I wound up exhausting myself. I asked myself honestly, “Why am I killing myself at my job?” The answer was so that I could do musical theater in the evenings and still keep a roof over my head. So I wondered, what if I could keep a roof over my head anyway, and just do musical theater? That’s when I hatched a plan and was confident I could make it work.

What were some of the biggest challenges you faced?
I had grown accustomed to a certain lifestyle, I had a mortgage, and I knew I wanted to move to New York City, but not as a starving artist. I had to figure out a way to pay my bills while pursuing my passion.

I decided to form an LLC which would own the intellectual property rights of the works I would develop. I sold 30% of the LLC to investors—raising enough to pay myself to work as an artist, and to have the wherewithal to get to New York, hire the best directors, casting folks, general manager and actors to make a big splash. It worked! This not only lit the fire under me to perform for myself, but also for the people whose money I’d taken to launch my career. My investors also helped introduce me to the right people and get me started down the right path.

What did you do to find success in your new career?
Aside from forming the LLC and raising enough money by creating present value out of future possible value, I had to prepare myself mentally to get up and work for myself each day. I had to be disciplined. It’s a lot like getting into a new diet or going to the gym. You have to get up and meet your goals. There’s a temptation to slack off or put things off. Having the discipline to stick with it, and setting concrete goals, was helpful, but the most helpful thing was actually setting deadlines and telling everyone else that you were going to have a product to show them by that date certain. That was a huge motivating factor.

What advice would you give to others considering a career change?
Don’t be unrealistic about what you can do on your own, and don’t make yourself miserable by pretending it’s somehow nobler to be poor and without resources. If you have a great idea, go monetize it first. With that, you’ll focus on the business side of things as well as the personal.


“It’s about keeping their eyes on the prize and trusting that they deserve whatever the end goal is.”

Lisa, 44
Moved from politics to law to career consulting

Career coach Lisa Fell Muñoz went through several career changes of her own. She spent several years in politics on Capitol Hill before becoming a lawyer. She was a successful attorney at the Manhattan District Attorney’s Office and, later, at two large private law firms. Now Lisa uses her experience to guide others through career and job changes both in and outside of the legal field.

What are the main reasons people change careers?
Statistics show that 80% of people are dissatisfied with their jobs. There are equally many reasons people change careers. Sometimes it’s based on a life-changing event, such as having a baby. For others, it is based on changes in the industry they are in. In some situations, it is to increase their income-earning potential. In other instances, it is a fortuitous circumstance. I recently read that Aaron Sorkin decided to focus on writing after he spent a weekend with a friend’s IBM Selectric typewriter and fell in love with the process. It can also be as simple as being unwilling to tolerate that nagging sense that he/she is in the wrong career.

What’s the best way to resolve doubts about making a change?
Doubt is a part of any change. Those who are forced to leave their careers, in some ways are the luckiest because they don’t have a choice. or those who do, however, it’s keeping their eyes on the prize and trusting that they deserve whatever the end goal is. I often hear people doubt they have the right to ask for whatever thing motivated their career search—be it more money, a fulfilling job, etc.

“Even legendarily successful people, such as Steve Jobs, have had to start over again.”

What’s the best way to prepare for making a career move?
Networking. People are more willing to take a chance on someone they know or with whom they are connected. Going back to school is another way to break into a new career. Also, starting slowly and either volunteering or starting something on the side works well. Sara Blakely, who founded the multi-million-dollar undergarment company Spanx, kept her job selling fax machines while developing her product.

How can you best find a second career that’s most suited to your interests, skills and natural talents?
It may sound obvious, but you will be most successful if you do something you like and at which you are naturally good. I would recommend a few things. There are assessments out there that gauge everything from a person’s motivators and behaviors to their overall personality. These can be very helpful in confirming who you are.

I would also recommend really observing yourself. To what are you naturally drawn? For what do people seek you out? What are you most frequently bringing to a situation? Ask people you trust what they think are your signature strengths are. What makes you uniquely you? In addition, discover what limiting beliefs might be blocking you. Are you still adhering to your parents idea of what your career you should have? Is there something you feel you can’t do that in reality makes no sense? Finally, explore. Talk to people in industries you’re interested in. Learn everything you can.

How can people with mid-level career qualifications succeed in a new career?
The biggest challenge is starting over. Humbling yourself to be a beginner again is not always easy. Remember, though, that even legendarily successful people, such as Steve Jobs, have had to start over again. Also, your financial obligations have often increased since your twenties. Knowing these challenges and planning around them are the best remedies. For example, understanding your spending habits and strategizing on how to cut them down in advance is helpful. Also, as with all challenges, have a plan in mind as to how to support yourself. For instance, it may be frustrating to be supervised by someone potentially younger than you. How can you bolster yourself while handling this situation?

To learn more about Lisa’s services, visit her webpage at