Ride Free 5-year Reflection, part 1

Then vs Now: changes to my money thinking and actions

For Ride Free’s five year anniversary this month (!) I’m taking you inside my financial story over the last five years: income, spending, and savings/investing. In this first post: what was different then vs now, what have I learned, and what made the biggest difference? I’m doing some of this storytelling over on instagram, too.


When I started Ride Free in 2015, I had the foundations of a mindful and intentional approach to money. I was already great at:

  • Budgeting the money I made
  • Tracking business expenses and revenue
  • Savings little bits at a time for my goals
  • Knowing how investment accounts worked

I was excellent at the day-to-day, which set me up well for the next level: financial futuring. I had to figure out how to make money and decide to have it for a future I believed I’d get to live SO i could progress my existing skills.

Now, in 2020, I am still good at budgeting and keeping track of ongoing expenses, but I also learned to manage and decide about larger pots of money:

  • Earn and make money. No longer freaked out by or judging making money + learned about how much money people make + strategic work choices = No longer underearning!
  • Utilizing an investing plan – for both regular and early retirement. My accounts reflect my plans for using them, not my hope they’ll somehow be enough.
  • Getting passive income – my time is worth so much more to me now


Through 2014 my greatest financial accomplishment had been buying and maintaining a conversion van during a terrible recession, and I am rightly still proud. I operated on a $5k imagination, because that was familiar.

By 2015, I realized I wanted to not have such a constrained money life and made the strategic decision to learn to invest in real estate, which was basically “how money works grad school but make it real life”. It forced me to focus, to try to get in a position to “get to” have mortgage debt and have it pay for itself. It changed the scale at which I thought about money, from hundreds to tens of thousands. The RE agent who told me in 2015, “Sorry – you’d have a lot more choices if you had a six figure job” was harsh, but they were right. 

In early 2020, when I closed on my third house while well into six-figure territory, it was easier because I knew more and had more. When the renovations cost more than I’d planned, it was merely annoying, rather than horrifically stress inducing like the first time. Not only did I have more skills and experience, I had more money to pad the process. Plus now, I own a cute house in a nice neighborhood, a mile from the public housing apartments I lived in as a teenager. My imagination scaled to $50k projects.


Then AND now I’ve always committed to only doing work I find interesting, under no petty dictators. Life is too short for boring or micromanagement. 

I got super strategic about honing skills that make good money — AND that I like to do. Yes, I was a pretty good comm director but the money sucked, and I was an ok full stack dev but I disliked lots of it. I’m much better at process design and strategic decisions. Most people aren’t, and so I can get paid well for my gifts.

Then vs now, my income sources were:

  • 2015 = dayjob @ a co-op, freelance, art 
  • 2020 = dayjob, consulting/facilitating, coaching, RE income


In 2015, my goals were short-term goals, like:

  • Fix my teeth
  • Afford to travel out of the country
  • Never have to suck it up at work and constantly jam oppressive systems

In 2020, my goals are mid-term goals, like:

  • Be financially independent (FI) by 50
  • Make sure I’ve got money for myself, my loved ones, and to give
  • Be able to afford opportunities as they come up
  • Always have autonomy at work and constantly create liberating processes