Taking Career Risks

martinis and your money

Taking Career Risks

So, for full disclosure, I recorded this episode almost six months ago while attending the FinCon conference in Charlotte, NC. I apologize to Kate Dore, founder of the blog Cashville Skyline, for the delay in releasing this; however, I wanted to save this episode for Women’s History Month where I am highlighting accomplishments of women that I admire and respect.

Kate has been a blog friend of mine for a while and I remember reading about her decision to leave her job about a year ago with no prospects and thinking that she was crazy. As Kate shares on the podcast, her decision was not as crazy as it seemed to an outsider; and it in fact led to bigger and better things for Kate.

What are we drinking?

Shannon brought martini supplies to FinCon so Kate & Shannon are drinking lime infused vodka with lemonade in plastic martini glasses.

Podcast Summary

  • For the majority of Kate’s career, she worked in the concert business as a concert promoter/talent buyer.
  • Kate knew a career change would happen eventually, but she knew she needed to get her money under control to make that happen.
  • She spent time throughout the years learning new skills for the career she hoped to eventually have.
  • When Kate finally quit her job, she had 6 months of expenses saved.
  • After a few weeks of doing nothing, she ended up taking a part-time job working for a ticketing company.
  • She was more nervous about depleting her emergency fund than finding a new job.
  • While Kate was not earning much money, she cut down to what she calls a bare-bones budget.
  • Kate thinks starting a blog is the best way to learn about digital marketing, which is the career she was interested in, and she said her blog is what helped her get her new job.
  • Shannon says she understands being unhappy in a job but says you need to be very thoughtful about where you are going before you quit.
  • Shannon thinks there needs to be more acceptance of crap jobs if you are planning to leave your current job.
  • Kate’s advice for someone who is unhappy in their career and thinking about leaving is that you should be networking all the time, not just when you are thinking about leaving.
  • Kate’s part-time job and new career both came from networking.
  • Have a plan before you make the leap of changing careers.
  • Shannon asks Kate what’s next, and Kate says she is focusing on continuing to build different streams of revenue.

Random Three Questions

  1. If you were to make a mix tape (Spotify playlist) of the greatest songs ever, what would be on it?
  2. What is the scariest thing you’ve ever done?
  3. If you could have a superpower, what would it be?

Have you ever taken any big risks in your career? How did it work out? Do you wish you could change careers?

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Shannon is a financial planner who left a “traditional” financial services firm to start her own company, The Financial Gym, because she felt traditional financial services firms did not have the tools or resources to help people in their 20s and 30s who are starting out and trying to build assets while also managing debt. She realized that the key to long-term personal financial success is a commitment to financial fitness and making smart financial choices. Through her blog, Financially Blonde, her book, Train Your Way To Financial Fitness, her podcast, Martinis and Your Money and The Financial Gym, Shannon is committed to making financial fitness fun, easy and accessible for everyone.


  1. I think focusing on different streams of revenue is the real key here – being able to chase after your dream job is so much easier when you still have a side income rolling in. Love the podcast – cheers, ladies! And Happy International Women’s Day!

  2. I am planning to make a career risk early this year. I am planning to resign and look for a better job. The next job I am planning to pursue is really not related to my course which is journalism. I hope I can enter in any public relations or any event management position.

  3. I’ve gone from a big organisation to a small one (not quite a startup but definitely a bit of a gamble). I’ve also changed career direction to a more lucrative and a growing industry as opposed to a struggling one and thankfully I love it!

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