How to be a Millennial Boss

First Feature: Millennial Boss

Welcome to the first post where I feature amazing bloggers in the personal finance / financial independence space! If I have learned anything from being in this community so far, it is that everyone is so welcoming and loves to help each other out. My main goal of this site is to inspire others to start their own financial independence journey, while giving them some great tips and stories that help them personally. And I have discovered that I follow a ton of bloggers because they all inspire me in different ways about different things. So let’s get started learning more about the people in this space, starting with Millennial Boss!


First Up: J from Millennial Boss

Who is this Boss?

J works a full time job in the tech industry, runs a successful blog, dabbles in side hustles, and now even has experience in owning a rental property! She is the definition of a BOSS. But how did she get where she is today and where does she plan to go in the future? Let’s dig in.

J attended her undergrad at a liberal arts school and obtained a liberal arts degree. After she graduated college, she moved back home because she wanted to work towards becoming a lawyer. So she started working as a legal assistant and realized that she wasn’t super excited with her job or living at home. To find a source of creativity and fun, she started her own blog! While many people that she knew were blogging about their own lives, J felt that living at home and working all her hours away was not going to be an inspiring blog. So she decided to write about what she loved – student travel.

She worked away tirelessly and her website was finally starting to get noticed! When a startup started to notice how well her site was doing, she joined them and decided that she was going to hack her way into the career that she wanted.

Time to Shake Things Up

First up, she started to change her resume to include experiences that she thought would be relevant to get into the tech field. And guess what, it worked! She landed an internship with the US Olympic Committee. While the focus of the internship was in Digital Media, it was really her first step into the tech field. She is also super glad with her experience there because she met her future husband there as well.

After her experience with the Olympic Committee, J again rearranged her resume and parlayed that internship into her first tech job. She also got married and inherited his portion of student debt as well! The two of them together were clocking about $89k in student debt.

It was around this time that J started to experience what many of us wish for, are experiencing, or have already gone through, Lifestyle Inflation. The happy couple bought a new 3,600 square foot house, she bought an amazing new car, a dog, went on lavish vacations, and financed all brand new furniture to fill their giant new house. While they were making very good money, lifestyle inflation has a way of making couples that have a ton of money start living paycheck to paycheck. J knew that she wanted to take her life and career to the next level.

For a long time, she thought that she wanted to go to Harvard Business School, as many students planned when she was in undergrad. After doing some research, she stumbled across the blog No More Harvard Debt, where she read about the struggles of a Harvard grad paying off his student debt. She decided that she wanted stay in the tech field and continue to hack her career, as she had already been quite successful with that strategy thus far!

She decided to enroll in an online technology graduate program, which allowed her to continue working and move forward with school on her own time and schedule. To avoid taking on further debt, she maxed out her employer’s tuition reimbursement program and spread out her school schedule to taking just a few classes per year. This allowed her to keep her job, go to school, and not take on additional debt.

The Turning Point

After being inspired by reading No More Harvard Debt, J and her husband wanted to blog about their own debt payoff journey. They felt that putting it out there for the world to see would keep them more accountable and work harder to paying off their own debt. And thus Millennial Boss was born. A place to J to creatively write about her experience as a manager in her 20s, travel tips, and life hacks. It was also around this time that she came across Mr. Money Mustache, who inspired her to check out the FI community. Her blog has now evolved into even more about her journey to financial independence, but includes amazing stories about how she paid off her debt, how she hacks travel and even her own wedding, ways that she has refocused her life, and what her future aspirations are (like living in a tiny home in the mountains, even if she thinks she could never really do it). She started her new journey in life with these four goals in mind:

  1. Stop linking salary to success
  2. Do what makes me happy
  3. Help others
  4. Become financially independent

The Interview!

I got to communicate with J to get to know her a little better. Here is what we talked about:

Thanks for letting me interview you! I really wanted you to be the first blogger that I featured as I have really identified with your introduction to the FI community, your focus on personal happiness, and the way that you hack your way through life. As someone who works in accounting, and even you as someone who works in tech, most people wouldn’t think that we were creative or would enjoy writing. Where do you think your desire for blogging comes from?

I kept journals all throughout college and although I’m horrified of what is in there now (if something happens to me – please burn them) it got me into writing and documenting my life through written word.

Blogging is the same thing. Although, recently I’ve moved away from thinking of my blog as a diary and think of it more as a platform to help people.

I think that’s a big misconception with blogs. They’re not diaries in the way WordPress or Live Journal blogs were 5-10 years ago.

They’re businesses and more professional than that.

I know you talk a lot about peer and social pressures to make certain decisions in life, whether they are career related, education related, or even car and house purchases. What happened that you finally decided that you were going to do things your own way? Like how you decided to not get your MBA and did an online tech program?

It feels a lot safer to hear how someone else achieved something you want and copy that exact same path to get there. It’s a lot scarier to try something new.

I realized early on that I didn’t have to copy the exact path of others who had the job I wanted or the life I wanted. I could try to do things in another way and still get the same result or close to it.

I think this type of risk-aversion is rampant even in the FI community. There are multiple wants to reach financial independence but there is a lot of fear about branching outside of the blueprint that many of the more popular bloggers have laid out for us.

You can really make progress (in my opinion) though when you’re thinking for yourself and drawing inspiration from sources but not straight up copying.

It seems like you had this epiphany moment about lifestyle inflation. You went from buying a giant new house, a new car, a dog, rooms full of furniture, expensive vacations and then flipped that on its head. You sold a ton of your stuff on craigslist, sold your car, and even tried to sell your big house but decided to rent it. What was that light bulb moment like?

I would call it more of a commitment. Everyday I had to wake up and commit to do something really scary (and being in a serious relationship, my boyfriend and now husband had to commit to it too).

There are times where we think back on our awesome house and we feel a twinge of regret. We have to train our minds to realize that the sacrifice was worth it.

There are more times though where we are grateful that we made hard choices in the last two years since it got us to a certain level of financial security today.

I’m guessing that the light bulb moment parlayed nicely into the decision to go after FI. Was that a discovery that you and your husband shared or was there some convincing him to get on board as well?

It took him years to get on board with the idea of financial independence. Part of it is that he didn’t have the same income I did to require researching which accounts the money should go to. If you don’t have disposable income to put into various accounts, than the concept of FI can seem daunting and so far away.

He was always a frugal person though so getting him onboard with that part wasn’t difficult.

The big change recently is that he has a more traditional job with benefits. He can finally start maxing out his 401(k) and contributing to accounts in the same way I have been.

It’s been a struggle for him because he really wants a new guitar and some fancy toys but he’s putting all of his money into our retirement funds instead.

I know that you are having some great success with your blog and now you even started your own podcast with Gwen from Fiery Millennial! And I know that you have some great friendships with many other people within this community. How did you start to make those connections and do you think those have helped you solidify your decision to achieve FI?

I started going to FI meet ups and events. The first one was the Chautauqua in Ecuador which brings together early retired bloggers and other FI-minded folks together to talk about money and hang out together. I’ve also been to FinCon a few times and local Meetup groups.

Making friends has kept me committed to FIRE. It also makes it more fun when you’re pursuing FIRE.

Gwen and I became BFFs because we both had millennial FIRE blogs. I left 5 comments on her blog one day and she emailed me and said, “I’m not going to respond to your comments individually. Let’s Skype instead” and we became friends from there.

Outside of just your blog and podcast, I know that you have tried some other sources of income. You operated an Etsy store for a while and you rent out your old house. Do you see yourself expanding your instances of side hustles, or do you think you’re going to double down on the success of the blog and podcast?

I should double down and focus on just the blog, work, and the podcast but that is not fun for me. Recently I found myself researching buying and flipping land in remote areas. 99% of the side hustles I research I don’t do, but I do start more side hustles than the average person.

The Etsy shop was probably the most fun and the house rental is easy.

You joke that you are obsessed with moving into a tiny house or an RV and move into the mountains. Do you think that this could be your FI future or where do you see yourself in your perfect post FI life?

I see myself having a very traditional life similar to the life that I had growing up. Funny how that happens?

I do want time for adventure though throughout the year so that part is different.

Finally, to wrap this up: What article / blogger would you recommend that people check out who are early on in their Financial Independence Journey? (Feel free to give a plug for one of your own favorite article as well)

Read both of these articles if you haven’t:

The Shockingly Simple Math behind Early Retirement

10 Years and a Day

Check out any of the MadFientist’s articles on tax optimization.

Also, give our podcast, Fire Drill Podcast a listen. We bring on some really inspiring guests and have a blast interviewing them about their path to FIRE or their incredible side hustles. Check it out at

Thank you so much letting me interview you! Your journey has really resonated with me and I think you’re a kickass Millennial Boss!

You flatter me. Thanks for featuring me!



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About Dave 11 Articles

I’m the Common Cents Millennial and I am here to change how you think about your finances. Follow me as I struggle with student debt, side hustling, budgeting, lowering my expenses, and my path to early retirement. My goal is to go from $150k in student debt to early retirement in 15 years or less!

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