Climbing the Corporate and Entrepreneurial Ladders | J from Millennial Boss

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In today’s episode, Cody and Justin bring you the boss we all strive to be. She realized being a lawyer wasn’t in her future and swapped career paths to the tech industry and never looked back. While she makes a hefty income with her day job, she maintains a dedication to side hustles.

We also loved J’s alternate take on Financial Independence by not rushing it. She loves her jobs and wants to be very stable. Just another great example of the many paths to FI.

Episode Summary

  • Studied political science in college
  • She thought she would become a lawyer
  • Became a legal assistant at age 22
  • She was in Boston and then moved back in with her parents
  • Some of her friends started blogging
  • She started her own blog about studying abroad to help students figure out where they should study
  • She finds an internship for the U.S. Olympic committee for digital marketing
  • Started working at USOC in 2012
  • All the experimenting with her blog directly translated with her new internship at the USOC
  • She turned that internship into a full time position where she would work with the field hockey team
  • She still uses a lot of the same strategies she did with her first blog including hiring out some posts on areas she isn’t as familiar with and  using keyword planning tools
  • One strategy she uses is to write content that’s funny and slightly controversial
  • She talks about the power of pintrest as the “Google of Pictures” and allows for tons of free advertising
  • J talks about how important it is to experiment with posts and pictures early on when your readership is low to figure out what works
  • She felt like the USOC job was great but wanted to learn from a bigger company
  • Her focus was on tech jobs in a fortune 500 company
  • She landed a job with an insurance company in Colorado as a project manager
  • She cited her management of a website that she helped a startup create with $15k as project management experience which allowed her to land the job
  • Her job was working with engineers to develop internal software
  • She got her Master’s reimbursed and got it in Information systems
  • Worked there for 3.5 years
  • She networked at the Grace Harper celebration
  • There she interviewed at a Silicon Valley tech company and made the move to California 9 months later
  • She received the scholarship to Grace Hopper Celebration
  • She got a pay bump from the move to California
  • Although the standard of living there is more expensive she actually lowered her expenses in Colorado by living in a tiny 1 bedroom
  • At that time they were in debt from student loans and other various debt
  • They became debt free in 2016
  • After a year of living in Silicon Valley she realized it was not for her
  • She moved to the pacific northwest where she feels she can get the best of both worlds
  • She loves her job so much now that she’s not hyper-focused on the retire early portion of FIRE
  • There is a desire to spend more time with family but she worked a deal with her current job to work remotely from time to time in an office near them
  • J’s list of best side hustles: Air BnB, Turo, and her new favorite — Etsy digital downloads

Key Takeaways

  1. You can never learn too many skills: J went to college for political science and now earns a majority of her money through tech and blogging. She was able to increase her perceived value by constantly gaining new skills!
  2. Design your lifestyle: Taking “risks” yields rewards. J was never afraid to take a leap at a new opportunity. Whether it was moving across states, trying new jobs, or finding a new role, her ability to take these risks vastly improved the trajectory of her life. Don’t be afraid to take calculated risks!
  3. Enjoy the FI journey: You don’t have to hit your FI number or reach your cash flow goals as fast as possible. J explains how she is enjoying her journey and soaking up as much as possible along the way.

Call to Action

How can you design your ideal career? Work to maximize your perceived value and leverage it to gain options.

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