Recent Posts

How I Paid Off $30,000 Of Debt Last Year

How I Paid Off $30,000 Of Debt Last Year

My relationship with debt has never been a resolute one. I’ve made a lot of mistakes along the way. I’m not an expert in personal finance and I still have a long road ahead, but I hope my experiences might help you along your own […]

Debt Payoff Report – December 2017

Debt Payoff Report – December 2017

Well, December happened. I took two weeks off but ended up having to work from home for the first week. A seemingly brief time for family and friends followed and then I came down with a cold to cap off the year. Happy New Year, […]

The Worst That Could Happen

The Worst That Could Happen

In some ways, the most enjoyable moments of our life are when we haven’t started yet. We haven’t added up the debt we owe, we haven’t calculated how long it will take to pay it off, we haven’t started saving or investing. All we know is that we will do it at some point in the future.. maybe tomorrow, or the tomorrow after that.

Instead of starting down the chaotic path of change, we continue to pour our energies into our romanticized shadow self, the aspirational self that we’ve curated over time out of the qualities we admire in others.

This avatar is so close to perfection that we become intimidated by the herculean effort that it would take to transform ourselves into them. We compare our current selves to our ideal selves and begin to think about all of the perfect steps that would need to happen along the way.

Rather than attempting the impossibility that is perfection, what if we considered a more mundane path? What if we just started now, in the midst of all our flaws, with our most insidious habits at their peak?

What’s the worst that could happen?

If we set aside the details and just took action, without considering every angle and without learning the theory behind every strategy, what’s the worst that could happen?

We’d feel overwhelmed, embarrassed, judged. We’d feel like we were missing out, or that we were failures.

Don’t we already feel all of these things? Staring down our dreams while we preemptively micromanage without making a single, tangible move to achieve them is overwhelming. It is embarrassing to reflect on the same resolutions, year after year, without ever meeting them. We do feel judged for our lack of evolution, and our inability to progress. We are missing out, and we will continue to miss out, because we haven’t prepared for our present or our future. We do feel like failures when we aren’t living up to our potential.

The worst that could happen? We shouldn’t even be worried about it. We’re there, right now. Ignoring our finances and delaying our freedom is the worst thing that could happen.

Start today, in all of your imperfect glory. Do one tiny, simple, achievable thing, and do it today. Sit down and write out all of your debt balances today. Open your bills today. Do a written budget today. Check out one personal finance book from the library today. Listen to one money podcast episode today. Calculate your debt free date today. Sell one thing today. Move $10 to your savings account today.

Don’t think about the implications of this one thing, or the emotions around this one thing, or the future actions that this one thing will set in motion. You can do more later, if you want, but don’t think about later. Focus on that one hurdle, and accomplish it now.

What’s the best that could happen?

If the worst thing that could happen is already upon us, what about the best thing that could happen?

You finally face an intimidating number and feel proud that you’ve made the first step. You put aside the past and begin to forgive yourself. You start to gain momentum, even with that one simple action, and feel like you have a future ahead. It won’t be perfect, and it won’t be easy, but at least it will be real.

First Or Last

First Or Last

If you’ve seen the movie Talladega Nights starring Will Ferrell, you’ll remember that Ricky Bobby, #1 NASCAR driver, lived by the last thing his father, Reese Bobby, said before walking out on their family: “If you ain’t first, you’re last.” Years later, Ricky and Reese were […]

90 Is Still An A

90 Is Still An A

My former roommate and one of my best friends in university was the textbook example of an overachiever. She would study at all hours, survive on coffee and adrenaline, and exist only in a frazzled, constant state of imposter syndrome. At times I was so […]

Debt Payoff Report – November 2017

Debt Payoff Report – November 2017

November was a little slow compared to recent months, and I’ve been mentally preparing myself for that. After a major win in October when I paid off $4,800, it was tough to be back to normal – or slightly lower than normal. It’s all part of the journey though! My lowest month in 2017 is still more than my highest month in 2016, so that’s something to celebrate!

One of the reasons for my lower payments this month was that I bought a laptop. I had recycled my previous laptop over the summer after owning it for ten years and hadn’t purchased a new one until this month. I started a second job working from home that I couldn’t do without one, so I decided to take the tradeoff of a low month now to increase my income in the future.

Including interest, I’ve paid $1,849.20 to my debt this month!

November Milestones

I made it under $60,000 on my student line of credit and I’ve also hit $25,000+ principal paid this year!


What’s up in December?

I’ll be getting a raise in December with a few months of back pay and I have two weeks off so I’ll be working a few more hours at my second job. Next month is going to be big!

The Zero Dollar Clothing Year

The Zero Dollar Clothing Year

I’m a fan of experiments, particularly ones that test boundaries and challenge complacency. In the past I’ve hit step targets and weight loss milestones (decent), skipped eating meals out for 100 days (manageable), and waited to purchase a new cell phone for a week after […]

My Heisenberg Moment

My Heisenberg Moment

Facing a desperate situation – a six figure student loan debt with no six figure income – I did what many graduates do at first.. I ignored it. I decreased my spending enough to make slightly more than the minimum payments. In some months I […]

I Love My Job / I Hate My Job

I Love My Job / I Hate My Job

My emotions surrounding my career are all over the place. Sometimes, I’m proud of my accomplishments and excited for the future. Sometimes, I want to curl up in a ball under my desk and sob until I pass out. Sometimes, I swing between these two polar opposites in the same hour.

Writing about financial independence and desiring a shorter career means that I often receive questions like “why don’t you just find something you love doing?” The truth is that I do love my job, as much as I could possibly love any job. I’ve never identified with the advice of ‘finding your passion.’ I’m a staunch generalist in a world built largely for specialists and I can’t think of a single career that I would be passionate about for more than a few years at a time. Not. One. Side note: If anyone notices a job posting for a full time Netflix watching aficionado, please forward it to me. On second thought, I’d probably get bored of that job too.

The reality is that I’ve done everything I could to ensure that my work would be interesting, varied, engaging, and rewarding. I’ve put myself in the best position to have a fulfilling long-term career, and it’s not working. I truly love my job, but I’m struggling to see past the next three years, let alone the next thirty-six.

Redefining Work & Leisure

The goal of financial independence for me has never been to escape a soul-crushing job. My objective is to make a series of transactions – every deposit into my investment accounts is the purchase of a tiny slice of freedom. Of course, this doesn’t necessarily have to mean freedom from work. More likely, it will mean freedom to pursue various interests on a whim without needing to consider financial compensation. Less catchy, but more accurate.

The irony of pursuing financial independence is that we’re often pressured to fit into a certain framework, just because it’s ‘optimal’ or ‘efficient’ (two words I’ve come to genuinely loathe) or because that’s how someone else did it. I can’t speak for everyone in such a diverse community, but not wanting to be limited is one of the reasons I was attracted to financial independence in the first place!

This is a new era. Work no longer has to mean putting in 40 years at a job, retiring at age 65, and spending the rest of your time puttering around your house until you die. Work has become more flexible, transient, and innovative. For the first time in history we can work remotely from almost anywhere on the planet. We’re starting to accept that work is a fluid concept.

The idea of retirement hasn’t been quite so fortunate. We’ve mastered flight, harnessed electricity, and mapped the human genome,  but somehow we still can’t shake the image of an elderly couple in adirondack chairs watching a beach sunset.

Financial independence has been backed into a corner too. I have no idea why we’ve taken such an intriguing concept and boxed it in so tightly that so many people think it needs to mean working at a job we may dislike for ten years while saving as much as possible, and then never receiving financial compensation for work again (ever! or else!). As more diverse voices enter the financial independence space, my hope is that the existing framework will be disrupted to make way for some new ideas.

I’m looking forward to following the social development that happens around retirement and financial independence in the near future, but in the meantime, let’s talk about my next decade of required employment. As far as work goes, I can’t complain too much. I know I’m extremely privileged to have the career I’ve had so far, and I don’t take it for granted. Would I choose to continue this job even if I didn’t need the money? That’s a question I hope to answer as my net worth grows.

I Love My Job

I am so thankful for my job every single day. Even on Sundays when I’m dreading going back to work, I still feel fortunate. In the last two years, this job has allowed me to afford living in an expensive city, start paying back my student loans, and invest in my future.


Much of my work involves helping others, and I thrive in that environment. I enjoy mentoring and encouraging those around me to succeed, and it’s rewarding to contribute to something greater.


I was fortunate to find a full time position after graduation. Many of my fellow graduates started with short-term contract positions, and some have yet to find work in the field. Outside of a fair salary, I have extended health and dental coverage and a pension match. A millennial with a pension match! It’s strange just thinking about it. I will also receive regular raises and bonuses throughout my career.


My job is a 9-5 salary position so I have predictable hours and I don’t usually need to stay late. I also have several weeks of vacation per year. Work-life balance is important to me and fortunately it’s encouraged in my workplace!


My boss is amazing. He’s an excellent mentor, a supportive supervisor, and a steadfast anti-micromanager. The best part? He’s willing to openly admit that he has advantages over me in some workplace situations because he’s male. Can we just take a moment and appreciate the rarity of that awareness? A compassionate and intelligent manager is one of the most important aspects of a workplace, and I am so grateful for him.


I have my own office, and I can close the door when I want. I also have a fantastic view, so that when I’m not staring into my screen for hours at a time I can get a glimpse of the sky.

Interestingly, many of these benefits would be irrelevant if I were financially independent. I wouldn’t need fair compensation if I had no debt and enough assets to cover my expenses; I wouldn’t crave work-life balance if I was free to build my own schedule; and I wouldn’t be excited by a nice office if I could work (or not) from anywhere I wanted. Purpose and mentorship I could easily replace through volunteering or expanding my network.

I Hate My Job

Switching gears abruptly, there are definitely aspects of my work that I could do without. If I had the financial backing to negotiate these facets of my job away, I’m not sure if my resolve to leave my career would waver. It’s worth a shot though, isn’t it?


I take the bus for about an hour each way every weekday. That’s a minimum of 10 hours per week on public transit. If we were to move closer to my office, we’d be paying significantly more in rent and also adding to my spouse’s commute. I listen to podcasts on transit which means that this time is semi-productive, but it makes for an exhausting day. If the system is running off-schedule or I fail to time my journey, I’m sometimes waiting in the rain or cold for the next bus.

I could buy a vehicle, but even after the upfront purchase it comes with its own added costs and inconveniences: parking, fuel, insurance, maintenance. I’d also still be in traffic for at least an hour every day, and my time would be less productive while I focused on the drive.


I try to be accommodating, but there are some projects in my roster that I would drop in a hot minute if I could. These tasks are things that need to be done but that I have zero interest in doing. When I’ve been at this job for slightly longer, and have more financial stability, I’ll attempt to downsize as many of these projects as I can manage. I don’t want to burden anyone else on my team, but I’ll feel more confident in asking if we could exchange work to better suit our abilities and interests.


Generally, most people I deal with in a regular day are fantastic. Every once in awhile though, I have to quell the urge to send strongly-worded emails. I feel financially insecure to the point that I find myself being too accommodating at times. The ability to be real with everyone at work, without being abusive of course, would be a major asset.

A Gilded Cage Is Still A Cage

On an average day, the love overshadows the hate. Would I choose this job over another job? Most likely. Would I choose this job over any job? I’m not sure. I haven’t been able to objectively figure out whether or not I want this job, because at the moment I need this job.

It ultimately comes down to freedom. Pursuing financial independence means that I can choose to work, or not, as my interests and priorities evolve. I can abandon a project that isn’t inspiring me. I can try something new without the pressure of needing it to be financially successful. I can fail, epicly and often.

If the benefits of my current job disappear, or a changing work environment means that I don’t enjoy my time here, financial independence means that I wouldn’t hesitate to leave. I wouldn’t be trapped in a career simply because I chose to spend more on luxuries in an earlier stage of my life.

If I do achieve financial independence, what’s the worst that could happen? I save up a ton of money and then decide I want to keep working after all? Big deal! What have I really lost – a decade of overindulgence? With the exception of a catastrophic event like a fatal accident or apocalypse where my life will be over before I can enjoy the outcome of my success, I won’t miss out on much by saving instead of spending. Even thinking back to my past levels of spending, there’s nothing I can really pinpoint that I miss. In fact, I’m happier and more content now than at any other time in the past. If my life is better now and later, where is the downside?