What Being Debt Free Really Feels Like After 1 Year


October 1st, 2015 – that was the day I officially became debt free and hit a net worth of zero dollars. Those first moments of publishing my facebook post, being interviewed by YNAB, and of course my (nervous) debt free scream were all incredibly fun and humbling. However, the day after I put in my last payment all that momentum I felt I had going seemed lost. Suddenly the biggest goal I had ever made, that was on my mind literally every day, that I had clawed and worked towards since graduating over four years ago, had not only come, but had passed. Sure I celebrated with a nice dinner and started planning for that first big vacation (that’s me on the left side of the pic on my first vacation), but those didn’t really excite or motivate me the way working towards being debt free did. I had trained my mind, my motivation, and my work ethic to work towards these very tangible short term goals of paying off specific debts, which all rolled into and contributed towards my bigger goal of becoming debt free. Now that was yesterdays news, and with each day that passed the ‘high’ of becoming debt free wore off. I couldn’t help but to ask myself, “what’s next”? Well, it was time to move on to the next Dave Ramsey baby step, so here is what that looked like back in October 2015:

  1. $1k Starter emergency fund
  2. Pay off all non-mortgage debt (Oct 2015)
  3. Fully funded emergency fund of 3-6 months of expenses
    • I average around $2 to $2.5k a month in spending, so I targeted $12k for this step
  4. Invest 15% of income towards retirement
  5. College fund for kids
  6. Pay off your home
  7. Live and give like crazy (aka retire)

Boom! I had my next goal of saving up $12k and it was time to get to work! Now keep in mind I was finishing out the highest income year of my life (as I should have been at that point in my life) and was sitting in October with a goal of hitting $12k ASAP. With the confidence of hitting my debt free goal FAR sooner than I ever expected, I wanted to push myself, because what’s the fun in setting easy goals! So I set my sights on getting that $12k saved before the end of the year. Yup, 3 months to save $11k (since I had my $1k starter fund already). BUT WAIT, Christmas is in December so there is no way that was realistically going to happen 🙁 … HAH, I had already been putting away $45/month in my Christmas fund in YNAB since last year so that I would have $500 by the time December hit – GOT’EM. I also decided to keep my lifestyle exactly how it was during my baby step 2 days, which was easy since that was all I knew. That meant the road was clear and I had to put away $5,500 in Nov and Dec, and you bet your ass that’s what I did! Well kind of, I had some money left over (~$600) in October since I was debt free. November I busted ass with side work and tightened the budget and was able to scrape together a whopping $8,144.15. Then December came and I put in $2,246.43 to hit the $12k mark before the turn of the year! Now I know some of you are thinking ‘dude you are so lucky to be able to make that much money’, and yeah, I agree with you to an extent. But you gotta know I worked my ass off doing side work and ended the year strong because I had a real, tangible, specific, time boxed goal and I made ZERO excuses for myself. For the sake of not rabbit holing, let’s save the topic of how I got to the income levels I am at (and how I keep expenses so low) for another day.

So now we land in January 2016 and go through the cycle of “YEAH, I hit my goal!” to “ok, what’s next” yet again. So for these next steps we actually do 4, 5, and 6 all at the same time. Let’s take a look:

  1. $1k Emergency fund
  2. Pay off all non-mortgage debt (Oct 2015)
  3. Fully fund emergency fund of 3-6 months of expenses (Dec 2015)
  4. Invest 15% of income towards retirement
  5. College fund for kids (I don’t have any yet, so this is a freebie)
  6. Pay off your home
  7. Live and give like crazy (aka retire)

Now at this point you might think – WOOHOO!!! Which I did for a day or two, but then I realized I had a major problem. I am currently renting a place here in Chicago and refuse to take out a mortgage, so step 6 should really say ‘buy a home in cash’, which is quite a feat. Now I know some of you might have just cringed or scratched your head when you read that thinking ‘he is crazy to throw all that rent money away’ or ‘why not just take out a loan and pay it down super fast’! Again, for the sake of not rabbit holing and getting off track, let’s save that conversation for another day. Back to the point – these are continuous LOOOOONG term steps & goals, with no real satisfying bite size chunks along the way (like paying off individual debt accounts). Maintaining motivation and excitement for these steps is going to be hard given how I have mentally operated leading up to this point. Now I’m certainly not asking for sympathy – my financial situation is WAY better than I ever thought it would be at this point. However, I am struggling to find a way to create that same motivation and excitement as I had before, which I genuinely enjoyed having and working towards. I still haven’t thought of a tangible, meaningful way to break these up, but if you have ideas please leave them as a comment below. I suppose part of me is writing this whole post as an attempt to give myself a pat on the back for how far I have come and to celebrate a milestone.

WHEW – So with all that said, let’s do some fast forwarding to catch up to where I am today:

  • In February I negotiated a $15k raise to go from $75k to $90k at my full time job (salaried)
  • Landed a few new side work clients with my business, and have pulled in ~$3k/month on average this year from M27 Marketing (a little lower now since seasonal clients are dropping off)
  • Paid for two vacations in cash (numbers shown here are all inclusive – flight, airbnb, food, activities, etc)
    • Spokane Washington trip in July to meet a life long friend of mine (pictured above) = $1,691.58 (cheaper since we got car rides from my friend and did some home cooked meals)
    • San Francisco/Sonoma trip in October (just got back from this) = $5,218.65 (higher since my g/f came with and I covered everything)


So finally we arrive at present day, which as of this writing is October 10th of 2016. Here is where I am at with my current goals:

  • *Total in retirement = $16,738.63
  • Total saved up for a house = $32,614.87
  • Total net worth (including retirement, house savings, and M27 Marketing) = $69,052.18

Looking at that as I type it actually makes it sink in a bit more and appreciate how far I have come in such a short time (especially while cash flowing two awesome vacations)! But as awesome as it feels to see my progress, come tomorrow this will be yesterday’s news. I am locked in and laser focused on buying that house in cash, so you can bet your ass I am not slowing down, but rather speeding up and getting more clients to hit that goal faster and ultimately retire early! Hopefully this inspired you in some way, and if you have any questions about anything just ask in the comments below, as I would love to hear from you.

Finally, I was really inspired by Pat Flynn over at Smart Passive Income for publishing his income reports. I’m not going to type up all the details like he does, but here is a screenshot of Septembers budget so you can see what a typical month looks like for me.



*as a disclaimer Roth IRAs have a maximum of $5.5k you can put in per year. Since the window for 2015 contributions extended into the first few months of 2016 I took the opportunity to just dump all of the 2015 contributions in the first month or two of 2016. This is why I have so much in retirement already.

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