Whenever people hear my title, Head of Global Well-Being, the commentary begins. People say, “Wow, that sounds like a dream job for you” or, “What exactly does that mean?” When others learn that my prior job was in Market Access Marketing, the conversations about my career start to sound like Mythology. Some insist that I transformed my job almost overnight. Another individual called the transition miraculous. But here’s the thing: it took me years to transition my career and even longer to find my purpose. I’m 46 as I write this piece. We are never too old to pursue the life of our dreams. And the peace of mind I feel every time I get ready to start work for the day makes the years of education, planning, and doing two jobs at the same time totally worth it!

Here’s how you too can go from day job to dream job.

1. Do More of What You Love: I call these items “extracurricular activities.” Remember when you were in high school and the guidance counselor told you if you wanted to get into “School X,” or do “Job Y,” you needed to be more well-rounded than just strong academics? Well, work and purpose follow suit. If you don’t love your current job and/or you aren’t sure of your purpose, try on other vocations for size. “EAs” can mean joining a resource group at work, or taking classes in the evening. Maybe your current company allows shadow projects or even full-time preceptorships. We learn what we love through experiences. And if you don’t love your first foray into a new field, you can always pick again until you find what you love. 

Bonus: When what you do outside of work lights you up, it becomes easier to stay positive in your day job.

2. Tell People What You Want: I am going to date myself here with this reference, but, as Cosmo always says, people aren’t mind readers. Especially when what you want from your next job is a complete departure from your current work. You want to be the first name on everyone’s lips when that coveted position comes up for discussion. I am not suggesting telling people what you want is a substitute for doing the hard work, but you will be amazed how many doors open up simply by telling people about your dream job. I literally would tell anyone who would listen (and even those who ignored me) that I wanted to be the Head of Well-Being. 

Bonus: The more you talk about your dream job out loud, the more you will believe it is a possibility.

3. Be Willing to Do the Job For Free (until you have experience): I know The Secret tells us that if we believe enough, and manifest enough our dreams will come true (and I believe that), but the book also tells us to act as if our dream has already manifested. There is no better way to do that, than actually doing the work. When I was starting out as a Health Coach, I gave free talks at grocery stores to hone my craft and find clients. Before my job in Global Well-Being, I ran a yearly well-being program in the US and volunteered as a Well-Being Champion. 

Bonus: If you do the second job for a company where you have already built your reputation in a different field, you are more likely to win your dream job without starting at square one in another organization.

4. Become an Expert: With devices galore and all the information we need on the internet, we have no excuse not to research topics that interest us ad infinitum. Most companies offer free webinars to draw business owners in for a sale: attend them. Most conferences are virtual these days and tickets can be purchased for a nominal amount of money. Run, don’t walk. Individuals who are already doing the dream job don’t have time to do the research they once did, but you do. By making time to learn about your desired field, you will have key information to offer up. 

Bonus: The information you gather not only shows your interest, but also makes you a more valuable asset to your employer!

5. Write Your Dream Job Document: LinkedIn and Glassdoor have thousands of job documents waiting to be perused. Writing your dream job document allows you to do a couple of things: 1) It helps you to get really clear on what it is that you want versus what you don’t want out of a job; 2) It enables you to fit the job requisition to your exact skills and abilities; 3) It saves the employer time. I have never met an employer yet who enjoys creating job documents.

Bonus: You might just end up in the job you wrote for yourself!


  • Kacy Fleming

    Head of Global Well-Being

    Kacy Fleming is a passionate advocate and believer that well-being and joy are cornerstones to a fulfilling career. Kacy is a TEDx Speaker, an award-winning well-being strategist, a frequent contributor to Thrive Global, and an M.A (masters) in Organizational Psychology. She is focused on empowering life-work alignment and creating equitable access to well-being resources and programming. Most recently Kacy has authored pieces on mid-life career transitions, women’s health, as well as a series on flexible work. In October she shared her thesis on “Factors that Affect Productivity in Flexible Work Environments,” at the New England Psychological Association Annual Conference. She is also a Certified Life Coach and Vinyasa yoga teacher. When she is not working, Kacy is an avid fiction reader, a downhill skier, and a seasoned yogi who enjoys watching mysteries with her partner Mark and dogs Otto and Finn.