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Dramatic Career Change, Minus the Drama

Dramatic Career Change, Minus the Drama

A few years ago I decided to make a dramatic career change. I had been with the same company for over 20 years and, even though I had had the good fortune to expand my expertise in a wide variety of areas, I knew that if I stayed, any other changes would be incremental. I wanted big change. I wanted to challenge myself and chart a new path for the next 20 years.

Of course, getting started is the hard part. I read numerous articles and “5 tips for …” blogs – all that left me with very ethereal recommendations. Some shared amazing, inspirational stories of people who left their “day job” to go follow their passion. Others were stories about people who went to run non-profits, or start their own business. But that wasn’t for me. What I needed was advice on how to start the search; a process that I have recently shared with a number of friends and former colleagues looking to do the same.

Here are my tips for making a bold move from your 20-year corporate past to your exciting next 20-year future!

1. Take inventory of your unique value.

You have been working for 20 years, building a career and expertise. Quite simply, you have a lot to offer any organization or role, but ultimately you need to focus on where you can bring the most value, and be the most valued, for your expertise. With a broad range of experience, however, focus on the areas you most want to use. I recently met a man who had spent 15 years practicing at a law firm and he now leads Business and Corporate Development for a startup. When he made the change he focused on the skills he wanted to use more (deal-making, managing complex negotiations, studying growth opportunities, etc.), and then looked for growing companies who needed this kind of expertise.

2. Know your “must haves.”

I have deep global experience; I lived and worked in Europe for many years, I am a dual US/EU citizen and have held global roles for the last 20 years. I knew when I started my research that I wanted my new adventure to have a global component to it, and, back to point #1, this was also a unique point of my value differentiation.

3. Hone your sector search.

For some it’s easy to hone the search; you know you want to move into the non-profit world, or you want to stay in a specific industry. For others, honing that search can be more difficult because you have a broader range of skills that can be of value to a broad range of industries. Finance is a great example. If you spent 20 years in various corporate financial roles, moving to a startup in a financial role is not going to be a dramatic change. But, if you join one of the growing Fintech startups, your financial background will be valued and your learning curve (and the fun!) will be on the technology side.

4. Size matters.

Focus on the size of organization you are interested in working with. If you love coordinating big teams, you’ll need to find a larger organization. If you want to get more up-to-your elbows in the work, a smaller organization will be your choice. I honed my search on organizations that were growing and scaling quickly for two reasons: a) I wanted to build and grow a team, but also dig in and do a lot of the work myself, and b) back to point #1, I had expertise in creating repeatability and predictability in a business that needs to grow and scale.

5. People always matter.

If, like me, you stayed at an organization for 20 years, you probably made great friends and worked with wonderful people. Never underestimate the benefits of working with people you like, who are fun to be around, and whose values align with yours. With a big change, there will be days when your confidence will be challenged, and having colleagues who are supportive (and nice!) will make all the difference in your new adventure. 


Leilanie Latimer is the Senior Director of Marketing at Zephyr Health. She is a marketing leader with proven experience taking nascent business ideas and products from concept to scale, with success in global go-to-market strategies, product marketing and planning, cross-functional team leadership, customer engagement, communications and employee engagement.

Have more questions? Follow up with the expert herself.

Community Discussion
Caroline Peani
Caroline Peani

great advice. thank you!

Friday, Mar 4 10:19 AM EST

Sharon Vaughn
Sharon Vaughn

ThIs advice is wonderful for what we can do on your end, but how can you get companies/ organizations to buy in to your "career change"? We know that our skills are transferable but I am hitting a wall when it comes to some employers buying in.

Friday, Mar 4 11:18 AM EST