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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? 

Debt Payoff Report – October 2017

Debt Payoff Report – October 2017

I’ve been looking forward to October for a few months, because some major funds were coming my way. I got a raise last year which was finally added to my salary so I had about a year of retroactive pay on my paycheque. Even after […]

Dynamic Timelines Of Financial Independence

Dynamic Timelines Of Financial Independence

Starting on the path to financial independence (FI) was hard. I had to come face to face with the consequences of my past decisions, including six figures of student loan debt. At the beginning, it was all overwhelming. When I first read about FI, I […]

Sunday Dread

Sunday Dread

If you’ve ever had a weekday work schedule, you’ll know the barrage of feelings that Sunday brings. You wake up Sunday morning with your heart beating a little harder, your chest constricting a little tighter, and your mind running a little faster. The task list starts to creep back in as the weekend hours wind down.

Sunday dread shrinks the weekend to Friday evening and Saturday, a whole 18 waking hours in my world. This means that just over 10% of my average week is relatively stress free. The rest of the time I spend working (24%), commuting (6%), sleeping (33%), or being otherwise occupied but still in a state of work-related stress.

Ditching the work week routine is my ultimate reason for pursuing financial independence. How can I live a healthy and fulfilling life when I’m almost constantly preoccupied with my job? One of the initial reasons I chose a 9-5, Monday-Friday career was that I saw others around me working 8-8, Monday-Saturday and I knew I wouldn’t thrive in that environment. Unexpectedly, I found myself mentally taking work home with me anyway.

I know part of my stress comes from the weight of student loan debt. Even the minimum payments add $1,300 per month to my baseline salary needs. When I’m debt free, my stress levels will go down but I suspect that the lingering restlessness will continue.

I’ve tried various ways of coping with this state of mind – the negative (shopping, alcohol, food) to the positive (meditation, exercise, therapy). Although I tend to feel better temporarily, the dread always seeps back in. I’ve come to realize that maybe I’m not the problem here – maybe it’s everything else.

Financial independence isn’t just another milestone to me. It’s a way to quiet down all of the noise in my life. When I no longer need to rely on a steady monthly income, I can dedicate more energy to work that allows me to feel productive but doesn’t flow over into other areas of my life.

Sometimes I think about all of us, many working in jobs we’re either ambivalent towards or outright dislike, and wonder about the impact we could have if we weren’t weighed down by the need to earn an income. What if we enjoyed our productive hours as much as our leisure hours? What if we weren’t stuck between anticipating the weekend or dreading the work week? What if so many of us were freed from the mental and physical afflictions caused by a society of overwork? Imagine how much we could accomplish together.

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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 relied on the credit card float and then paid it off in others with tax returns or bonuses. I never felt like I had enough money to get through the month. I tried to budget and almost always failed to stay on track. I felt like I was waiting for this ten year sentence to end so that I could finally just start from zero again.

I want my life back. Please tell me … how much is enough? How big does this pile have to be?

I spent the first year of my debt repayment journey tracking my spending and pretending to budget. I made $15,000 in payments to my debt that year, and at the time I felt proud of that accomplishment. I’d paid about $800 more than the minimum payments, which seemed like great progress.

At the end of the year, I had to calculate the interest I’d paid on my student loans for a deduction on my tax return. Out of $15,000 in payments, the interest totaled almost $5,000. FIVE THOUSAND DOLLARS. Just in interest. To this day, I have a vivid mental image of throwing stacks of bills on the ground and setting them on fire.

It all hit me then, harder than ever before – I was staring down another ten years of payments, and another $20,000 in interest. I was making an average salary for my city, but I was struggling somehow.

At the beginning of my second year of payments, I knew I had to make some major changes. I was ready, but I wasn’t prepared.

I’m a relatively privileged person – I’m white, educated, and I was always encouraged to be productive. When it came to money, I started out well behind the curve. Money was never something positive during my childhood – it was something you needed, something you fought about, and something that you earned somehow but that disappeared somehow. Our house was always ringing with the noise of money fights – I’d lock myself in my room with headphones in for hours to find some quiet. My parents always made sure we had enough, and I’m grateful for the way they provided for me and pushed me to succeed. I was just missing the money framework that seemed to come so naturally to others.

I knew generally that frugality was beneficial, that you should live within your means, that you shouldn’t take on debt, that you should save for retirement. I knew the theory, but I didn’t have the practical skills. I didn’t know how to budget properly, or what you should do if your numbers weren’t working out. I didn’t know how much more prepared food cost, or how to cook inexpensive meals at home. I saw how others were spending their money, and I emulated it. I thought I just needed a higher income.

The moral of the story is: I chose a half measure, when I should have gone all the way. I’ll never make that mistake again.

There was one thing I did know – my plan wasn’t working. I needed to find other plans. When I searched for resources, there was one name I kept running into over and over: Dave Ramsey. At first I was skeptical, particularly about taking advice from a person who was so opposed to some of my major values, but I decided to be an adult and listen to the plan – even if I didn’t fully agree with the personality behind it. I started listening to his podcast on my commute, and I listened for the full three hours every single day. I haven’t missed one episode in an entire year.

Every month another lightbulb went on as I listened to all of the debt free screams and the millionaire calls. I started doing the math on how much my debt was costing me every month. I compared prices on groceries. I used habit trackers to mark days where I spent $0. I did challenges and experiments. I went 100 days without any meals out. I stopped buying clothing for a year.

Every month I felt a little more confident. I went from making $40 in extra payments every month to $280, to $700, and now to $1,200+. This wasn’t a switch I turned on that suddenly gave me the skills and habits I needed. This was a constant daily struggle to overcome more than a decade of ignorance.

Dave Ramsey gets a lot of love, and a lot of hate. I’ll just say this – if you’re privileged or lucky or educated enough not to need his help or understand why others do.. just be grateful for that and shut the fuck up, okay?

It is not easy to budget and follow through on that budget if you’ve never been shown how to do it correctly.

It is not easy to meal plan and buy groceries with a list if you’ve never been shown how to do it correctly.

It is not easy to defer your desires and save for things instead of paying with credit if you’ve never been shown how to do it correctly.

For some reason we treat managing money like an innate human ability and if someone isn’t successful at it right away it must be because they’re lacking in intelligence or willpower or strength of character. We should be treating managing money as a necessary skill that some of us were just fortunate to have mastered early on.

If someone’s trying to learn how to swim, you don’t just show them a chart and tell them how obviously easy it is. You wade in. You instruct them to float. You teach them how to tread water. You demonstrate different techniques. You get in the water with them and show them how to splash around for fun. If they’re drowning, you don’t shout physics equations or insults or misplaced words of encouragement from the deep end like a total sociopath. You jump in the water and help them, or you stand quietly to the side while the lifeguard helps them.

You clearly don’t know who you’re talking to, so let me clue you in. I am not in danger. I am the danger. A guy opens his door and gets shot, and you think that of me? No! I am the one who knocks!

Coming up on two years of this journey, I’m not the same person I was before. I’m not at the mercy of a bank. I don’t nervously log in to my accounts after avoiding them for weeks. I’m not afraid to check the mail. I don’t panic at the thought of an emergency. I’m the one who knocks now. I say when I’ll be paying this debt off. I say how much I’ll be earning. I say how much I’ll be paying in interest.

I didn’t start with this confidence – it grew as I learned how to manage money, month by month. I’ve cut my spending by thousands of dollars per year. I’ve received raises and bonuses, and directed most of that to my debt too. I started a side hustle to shorten my timeline even more. Instead of $15,000 in payments, I’ve doubled that to more than $30,0000 this year.

I plan to pay off my debt in 2019 instead of 2026. That’s more than SIX YEARS of my life that I’ll get back because I started to pay off this debt faster. If you saw my spending from last year to this year, you would swear they belonged to two entirely different people.

The best part? It wasn’t a sacrifice.

I did it for me. I liked it. I was good at it. And I was really — I was alive.

It’s amazing how much we can adapt. When I started to make changes, the first few days and weeks were tough. I wanted to quit. I relapsed occasionally. I made mistakes. I overspent. I caved. I stumbled.

It was all worth it.

The truth is that I feel happier and more content now than I ever have in my life.

Now say my name.