Work Optional with Tanja Hester


Work Optional with Tanja Hester

When I last had this guest on the podcast, she was still an anonymous blogger who was just on the verge of making the leap to a public outing and declaring financial independence with her husband. Fast forward over a year and now she has written a book to discuss her experience leading up to financial independence and why she’s not a typical FIRE (Financial Independence Retire Early) persona. I’m excited to have back on the show, and for the first time publicly, Tanja Hester, author of Work Optional: Retire Early the Non-Penny Pinching Way, founder of Our Next Life Blog, and co-host of The Fairer Cents podcast. 

What Are We Drinking?

Tanja — Coffee with a splash of cream

Shannon —  Black Cherry Schweppes Sparkling Water

Podcast Notes

  • Tanja recently wrote a book called Work Optional: Retire Early the Non-Penny Pinching Way.
  • When Tanja was last on the podcast, she was a few weeks away from retiring from her job and revealing her identity on her blog Our Next Life.
  • One of Tanja’s concerns before leaving her job and declaring financial independence was how she would feel emotionally. She had spent years with the people she worked with and had many professional relationships. 
  • Tanja spent a ton of time thinking about how her identity would change and how she would feel worthy in the world without contributing through traditional employment. She suspects the transition was good, because she thought about the emotional aspect of it ahead of time.
  • After she left her job, Tanja actually thought about work less than she expected. She was surprised how quickly thinking about work left her head and she pivoted into the next thing. She believes it is because of the preparation and thinking through that transition.
  • In researching for her book, she found that those who celebrate the end of one part of life (retirement) and treat it as this big moment are much happier than those who are forced out. Closure helps the transition.
  • The transition for Tanja and her husband, Mark, was pretty smooth, but there were some new rhythms in their relationship they needed to figure out. Some things were better than expected.
  • One of Shannon’s fears is not being prepared for transitions in life, which is why she believes in the importance of an emergency fund. Preparation makes things so much easier to handle.
  • We can’t predict the future and we don’t know what might happen, but if you are planning a big life transition, mentally prepare yourself, because even really good changes often feel scary and can feel like a loss. Knowing that it can be sad or stressful can make it easier to cope with. It helps you let yourself off the hook.
  • Last summer was really tough for Tanja, because things were progressing with her disability and she wasn’t able to get outside as much as she wanted to. She was feeling depressed, but reminded herself that she doesn’t have to go to work and tried to think about the positive parts of her life. Feel the sadness, but don’t add extra sadness by beating yourself up about being sad.
  • Shannon is a big fan of feeling all of the feelings. In April 2018, Shannon had a lot of struggles with the Financial Gym, and it set off some emotional alarms. It was her aha moment that it is okay to have these feelings. A glass of wine and a good cry in the shower helps.
  • Tanja’s was in her late 20’s when she decided she wanted to retire early, because she realized the career promise, you climb the ladder and life will be happier, is not necessarily true. We live in a burnout culture and every time you move up the ladder, you make more money and it is good for your ego, but you trade in all of your free time.
  • Tanja’s dad has a disability that forced him to leave the workforce in his early forties. It has always been clear that she may get what he has, and it turns out she has had it all along. It is a genetic disability called Ehlers-Danlos Syndrome (EDS). She probably won’t get his particular manifestation of it, but she is getting other effects.
  • In her early 30’s, she realized that she may only have a decade left of full mobility and she might not be able to climb mountains her whole life or travel the way she wants to when she gets older. Work was also getting busier and busier. She needed to get on a different path. 
  • Tanja avoids the term FIRE (Financial Independence, Retire Early), because she doesn’t think working a job is bad.
  • If she had retired at 30 or 35, she thinks she would have missed out on an important chapter of her life. For anybody who looks at the FIRE movement and thinks they missed the boat, there is a trade off. Those who retire early could potentially be missing out on something. Look at your own situation and figure out what is important to you. Value your life experiences for what they are. 
  • Shannon recommends running your own race. It doesn’t matter where you are going, it just matters where you want to go. You can run a marathon at any point in your life. Who cares if it takes you 30 years instead of 20.
  • Shannon likes the FI of FIRE. FI, Financial Independence, is the goal Gym trainers give their clients. It is the ability to work because you want to work and not because you have to work. If you want to keep working, have at it. It is a freeing idea. Any time before 59 1/2 is early. It doesn’t matter your age. 
  • Tanja ran one marathon and she is banned by her orthopedist by running anymore, because of her disability. She ran it very slowly, her time was 5:25. She views it as an accomplishment, because she ran for five and a half hours.
  • There is something to sticking with a goal for a longer period. You will always be slower than someone else. Sticking with frugality, saving, or investing for a long period is worth celebrating. We are all unique and are all on our own journeys.
  • As a society, we are really bad at teaching people how to value ourselves outside of a work context. The idea of the American dream is focused on “If you work hard _______”. The whole vision is tied to work. It does have its merits, but if you are trying to take yourself out of that paradigm, it is difficult to know your worth.
  • Tanja has heard from some of her blog readers that they reached FI and felt aimless, and it was difficult for them to get out of bed everyday.
  • Tanja spent a big chunk of the book talking about self worth and who am I, when work is no longer a part of my identity.
  • The biggest surprise of early retirement for Tanja was realizing how much she loves working, but on her own stuff, not for an employer.
  • Tanja was a consultant for 16 years and her name wasn’t on anything. Now it is on a book. Getting to own what she does is such a gift. 
  • We are not all raised to define our worth outside of the traditional view of employment. 
  • If someone asks Tanja what she does for a living, she responds based on how she feels. If she is feeling saucy, she will say “I retired!”. Most of the time she will say she is a writer. Getting to say that feels like a privilege. 
  • Retirement is still a new concept. The idea that it is one fixed thing is an idea Tanja wants us all to move away from.
  • Shannon never connected with retirement, because she wants to work. The idea of FI came to her when she worked at Merrill Lynch, and it sounded so much better. 
  • Shannon is trying to reframe retirement as FI, because retirement is too far away. The purpose of preparing for FI is to give you the flexibility to discover your big thing in life. 
  • Tanja wants to kill the idea that you need to know early in life what you are cut out to do. Over her desk, Tanja has a picture of Julia Child in her kitchen in France. Julia didn’t learn to cook until she was over 40 and she went on to be the greatest cooking icon of all time. She was able to pursue that, because her husband had a job that supported them and she had financial flexibility.
  • The power comes from just knowing you can quit a job that sucks. Knowing you are good for a year is incredibly empowering. Early retirement doesn’t need to be your goal. Semi-retirement includes scaling back on work to allow yourself to do other things that are more meaningful to you. Sometimes you don’t need full retirement.
  • Two best financial tips to help you reach FI: 
    • If you have an employer match on your retirement account, you need to get the full match. It is free money – get it as soon as possible.
    • Automate your savings and hide it from yourself. Keep it out of your checking account and continue to increase the amount. Keep challenging yourself and see if you can do it. 
  • You don’t need to cut every single expenditure, just cut the excess stuff, the mindless spending, that doesn’t make you happy. Spend money on the stuff you love, without guilt.
  • When you cut back on the crap, you have the stress-less ability to spend on things you love.
  • The Gym tracks spending on 1,700 clients. The top spending areas are food/dining out/food delivery, Amazon, and Uber/Lyft. Create more mindfulness around your spending. We work hard for our money, and we need to make it hard to spend our money. It is too easy to spend money and we are not paying attention. 
  • Tanja’s book takes a balanced approach to achieving FI. She takes readers through the emotional and existential choices of FI to help you get on the right path. The book includes questions, checklists, and other tools. 
  • Tanja had a dream of writing a book and she feels better than she expected she would now that the book is finished. Her experience was very positive and she is really happy with how the book turned out. 
  • The book publishing experience is a reminder, over and over again, about how much you cannot please everyone. It isn’t the perfect book for everyone, but that is the nature of writing a book. She is proud of what she put into it and had a positive experience with her publisher and editor. She wanted to write this book for people who are not money nerds.
  • Tanja wanted to write a book that was more inclusive. She wanted it to help people who are single, people who have kids, people who don’t make six figures, people who have a non-traditional career path, and people who didn’t go to college. She wanted all of those people to feel welcome and see themselves in the book. She also wanted to break apart the concept of early retirement, to show that it is not all or nothing, and to write something the lets people decide for themselves what adds value to their lives. Tanja feels like she has accomplished those things. 

Takeaway: My biggest takeaway is that financial independence and the road to it and through it can be different for everyone. The most important decisions you can make on your financial journey are the ones that resonate most with you and bring you joy at the end of the day. Although I can’t think of anything more joyous than living a work-optional life.

Random Three Questions

  1. What would be your second book you would write?
  2. What is the next big trip you would like to take?
  3. What is something that has to happen every day for you?

Connect with Tanja


Book: Work Optional: Retire Early the Non-Penny Pinching Way 

Podcast: The Fairer Cents

If you’d like someone to help you figure out if you can live a work-optional lifestyle, I hope you’ll reach out to my team at the Financial Gym. We have hundreds of clients currently on this path, and we’d love to help more.

In case you didn’t know, Martinis and Your Money listeners, and your friends, get 15% off services at the Financial Gym. If you’re ready to manifest your work-optional dreams in 2019, head over to to get signed up today.

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