Career Change Advice with Dana Cowin


Career Change Advice with Dana Cowin

I end every show asking you to tell me what you want to hear, and I love when you take me up on it. This week’s show comes thanks to my listener Lisa who said, “How about a show on midlife career change, pivoting, reinvention, etc. I’m a full-time working mom of two boys, 11 and 13. I was the first person in my family to go to college and worked three jobs to pay my own way. I couldn’t wait to get to corporate America, and I have been a successful sales rep for 20 years and have learned a lot, but as I approach my 50th birthday I feel like I need a change. There seems to be a lot of focus in the media on Millennials, but how about the Gen-Xers? I’m sure there are a lot of us who feel the same way and don’t know where to start (so we don’t) or what resources are available or are afraid to change for many reasons, i.e., How do we translate our current skills to a new position? Can we maintain our salary level? Do companies view us as too old? etc., and would appreciate some direction and maybe a kick in the pants to get started!”

Well Lisa, ask and you shall receive, and I am not just talking to any old career expert today, I am talking to a girl crush of mine, Dana Cowin, the Former Editor and Chief of Food & Wine magazine and podcast host for Speaking Broadly. Yes, THE Dana Cowin, who was at the helm of all that is great about Food & Wine. Dana and I became friends through the Bacardi Women’s Empowerment Series and she frequently discussed how she became a career guru, so I put her knowledge to the test on my show. Dana has so much great information from her personal career
change experience but also mentoring hundreds of people over her extensive career. This show is great for anyone at any stage thinking about making a career change.

What are we drinking?

Dana — Chambord and sparkling wine

Shannon — Chambord and sparkling wine

Podcast Notes

  • Dana began her career at Vogue, in features, in the 80s. Since then she has worked for House & Garden magazine, Mademoiselle, and Food & Wine magazine.
  • When Dana worked in the Condé Nast building, she could tell exactly which floor people worked on when she saw them in the elevator, by the way they dressed.
  • She was promoted to Managing Editor at House & Garden and Editor at Food & Wine. After 30 years in the magazine business, at age 55, she was ready for a change.
  • Dana was told by someone at a technology startup that nobody would ever hire her, because she is too expensive, too old, and not digital enough.
  • To those people who are looking to make a change, Dana recommends having honest conversations about what you want to do.
  • Dana left Food & Wine to work for a company called Chef’s Club for a year.
  • Any time you build your reputation in an industry, you take it with you.
  • Shannon said to treat your network like a garden: water it, tend to it over time, and it will bear fruit when you need it.
  • Shannon randomly emailed a connection on LinkedIn when she was fundraising for the Gym, and the connection ended up investing $50,000.
  • If you are jumping from one industry to another, you may need to do a side hustle to build a new network.
  • Dana mentored employees at Food & Wine. The conversations that were most productive were those she had with employees who were not performing well. The more she became a leader in the industry, the more people in the industry would come to her.
  • There are typically three thoughts processes people have:
    • You have the gut feeling that you are not in the right space
    • You get fired
    • You want something more, but don’t know what it is
  • Once someone has identified the problem, where do they go next?
    • If you don’t like the boss, but you like what you are doing, you are in the best place. You can work for someone else and it is the easiest transition. The most difficult is if the person doesn’t know what they want to do. This is common in people ages 25 to 33.
  • You need to own your situation. Don’t get stuck on blame or fear.
  • For people who get pushed out, how do you help them assess how to find the next thing?
    • When people say “I have no idea what I want to do”, they typically have an answer after talking to Dana for an hour. People need someone to listen and write it down for them.
  • Dana has a three-minute test she gives people: write down the things you are really excited about on a piece of paper and don’t censor yourself. Look at the words and connect them together.
  • Shannon said to enter key words into LinkedIn search and it will bring up different jobs. Women feel like they need to have 100 percent of the qualifications, while a guy only needs 20 percent to have confidence. At a recent women’s money retreat, it was said to think like a mediocre white guy and act with that type of confidence.
  • Interviewers are looking for communication and intelligence. Are you able to be trained? Are they able to work with you all day? Be the most authentic you!
  • If you are trying to find a job, show that you are a hustler. If you are working and going to school, make sure to highlight it.
  • What do you want to do? What can you do? What skill sets are transferable? People who are in their 50s and 60s tend to pivot to consulting or limited-time work. It can be a wind up, not necessarily a wind down. Older employees can capitalize on their expertise.
  • The more change you make, the more comfortable you are with it. Keep flexing that muscle, because we live in a world of change. There is so much freedom to move and there is a benefit to it.

TAKEAWAY: You’re never too old for change, and change might be exactly what you need. With a little research, self reflection, and conversation, your next greatest chapter is awaiting you.

Random Three Questions 

  1. What story were you particularly proud of?
  2. What is a show you like to binge watch?
  3. What do you do to relax?

Connect with Dana

Instagram/Twitter: @fwscout

Podcast: Speaking Broadly

If you need someone to chat about finances or career changes with, I hope you’ ll reach out to my team at the Financial Gym. We’re constantly working with our clients to make sure that they’re making the right choices that not only make sense financially but also make sense for their personal life journey. You can schedule a free call here to find out more. No matter where you are in your financial journey, my financial trainers can help you get where you want to go. So head over to or send friends to to sign up today!



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