My Biggest Money Challenge? Not Knowing How To Start

Listen: we all have money challenges.

Some of them are (relatively) easy to solve, but others are big and thorny and no fun at all.

My friend Andrew at Family Money Plan is running this interview series, where he interviews other bloggers, and one line of questioning in the interview really stuck with me. To paraphrase his awesome questions (and not give away any of the interview!) it boiled down to

“What was your biggest money challenge?”

Ooof. Am I allowed to answer with a year?

Because if yes, the year was 2012.

To totally date myself, that’s the year I graduated from university, and started working in the world on my fancy not very fancy new-grad salary.

That I had no idea how to manage.

I knew the basics, and it’s not like I went out and lifestyle-inflationed it up on a high-interest credit card. But I also didn’t realize that maybe my aggressive savings goals and inflexibility would put me in line for a world of stress as I tried to save 30% of that entry-level salary.

What do I mean by world of stress?

Oh boy, I’ve been meaning to tell this story for ages.

Once upon a time, it was 2012, and my mom graciously drove me to Ikea to pick out a new $49 desk for my fancy decidedly student-style apartment. We got the desk, had a great time and made it back to my apartment unscathed.

I pulled the desk – which, let’s be real, was not that big, there’s only so much $49 will buy you, even at Ikea – out of the car and made my way towards the apartment.

And then I tripped.

Because I was carrying this awkward box full of desk, I wiped right out, and my knees took a huge beating on the pavement. That wasn’t even the problem though.

I was wearing my only pair of nice jeans at the time. Now that?

That was a problem.

Such a problem, in fact, that I went straight into full money meltdown mode.


My budget was so tight that the thought of replacing a $40 pair of jeans, after spending $49 on a new desk, was absolutely unthinkable. Meanwhile, yes, my retirement accounts and “emergency fund” savings were getting big chunks of my paycheque every two weeks.

So on “typical” measures of money management, I was killing it, right?


Crying over a $40 pair of jeans is nowhere in my definition of killing it.

With the benefit of hindsight (because isn’t that always the way?) I can see now that I could have been a little bit more relaxed, and acknowledged that maybe – just maybe! – the strident adherence to what I thought was “the best and only way to manage my money” wasn’t necessarily working for me.

I mean, my god, I cried over a $40 pair of jeans. I never want that for anyone.

When I look back on it, I think the root of of the issue, and my real biggest challenge, was that I had no real idea where and how to start being an Adult With Money.

I had great examples and teachers growing up about how to manage money, but I didn’t really know – like, on a detailed, step-by-step level – how to look at my monthly income and turn it into a reasonable, realistic plan for myself that didn’t leave me crying over a pair of pants.

I started Half Banked to chronicle the current phase I’m in with money, and my (yes, sometimes ridiculous) attempts to save half of my income. But the absolute best part of this whole experience, by a long shot, has been hearing from friends new and old that somehow, this little corner of the internet where I overshare about money has helped them in some way.

So I want to do more of that, and can I ask for a huge favour?

I need your help.

I’ve created a super-quick, 4.5 question survey to help me figure out how I can create more content that actually helps you with the biggest money challenges you’re having right now – even if it’s more “I want to buy a house someday” and less “I’m crying over a pair of pants.” To each their own, OK? We all have our stuff.

And I mean, how can I judge anyone after crying over some pants, right?

It’s totally, 100% anonymous, and after having the all-stars on my email list send me some answers this weekend, I can guarantee it takes an average of just under 2 minutes to fill out (ahem, and if you have 60 extra seconds, you can even create a budget with the One-Minute Budget. I’m all about efficiency guys.)

The survey is closed now, but a giant thank you to everyone who participated!


As if I wasn’t already honoured enough that you made your way here to read my ramblings about money on the internet, I am beyond grateful for the time each and every one of you took to fill out the survey. I seriously appreciate it, and I’m going to repay the favour by addressing as many of the survey answers as I can over the next however-long-it-takes!

I mean, given how much fun I’m having, we’ve got years of me oversharing about money on the internet ahead of us, friends.

There’s totally enough time to get through all of them.

If you’d rather share in the comments, I’d love to hear – what would you say the biggest money challenge is that you’re having right now? Or do you have any new-grad money stories to share? I’m fine being the only one who has cried over pants, but if you have other funny-in-retrospect stories, I’d love to hear them!