Start with the Envelope

Start with the Envelope

Start With the Envelope

Most people don’t ease into looking at their finances. They wait until the discomfort of not looking outweighs the discomfort of actually doing it, then they do it all at once, under pressure.

I get it. I’ve done the same thing with plenty of things that were genuinely good for me. Exercise. Eating well. This blog. Something about human nature resists doing the good-for-you thing until it becomes harder not to. I call it reactive mode. That’s where most of us live.

If you’ve never built a real picture of what you spend, the word “budget” alone is probably enough to make you want to stop reading. Fair. It’s a loaded word. But you don’t need a full budget to start. You need one small habit that gives you real information.

Here’s where I’d start: pick one category. Lunch is a good one, since it’s small, contained, and easy to track without much effort.

For two weeks, get an envelope, label it “lunch,” and keep every receipt that touches that category: restaurant receipts, grocery receipts with lunch items on them, all of it. At the end of the two weeks, add it up.

That’s it. No spreadsheet, no full accounting of your life, just one number you didn’t have before.

Once lunch feels manageable, do the same thing with dinner. Then do the same with whatever else you’re curious about. You get to choose what you track next, and no rule says you have to track everything at once.

Small, gradual changes tend to stick better than dramatic overhauls anyway. I know someone who overhauled her entire diet by cutting one thing at a time: milk from her coffee first, then one small change every couple of weeks, spread out over a year. Nothing about it was fast, but nothing about it fell apart either.

The same logic applies here. You don’t need the whole picture on day one. You just need to start seeing one small, honest number, and let that be enough for now.

Not Enough

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Not Enough

What’s your relationship with money? I ask because I’ve assumed for a while now that yours looks something like mine. Lately I’ve noticed my assumptions tend to get me into trouble.

Here’s my money history, in case it helps you check.

I’ve always operated from one core fear: there isn’t enough, and it might run out. That thought shows up everywhere. I check my finances compulsively to confirm there’s still enough today. I’m frugal to a fault, hand-me-down queen, proudly. And spending money hurts, whether it’s on something fun or a plumbing bill. All of it stings equally.

Funny enough, I know people with the same fear, not enough money, who respond by spending as fast as they can before it disappears: same fear, opposite behaviour.

My fear came true when I separated from my husband. He’d been the one with the paycheque, and suddenly the money I’d been afraid would stop flowing actually stopped. I believed my savings were gone too, most of it eaten by the lawyer and the split. Nothing is more terrifying than watching your worst fear materialize. It took over my life for a while.

Eventually I had to find a way to let go of “there’s not enough,” because that thought was the thing actually causing the pain, more than the situation itself.

I started permitting myself to spend on things like clothes or eating out, without the usual sting attached. I also started increasing what came in, while still making sure I never spent more than that. Not more spending for its own sake, just less fear attached to the spending I was already doing.

Looking back, my money history wasn’t all bad. My obsessive tracking gave me an unusually precise understanding of exactly what I need to live on. My obsession with an emergency cushion meant I actually had options when the divorce hit. Both of those habits, born from fear, ended up serving me well.

Now my relationship with money is different. My baseline thought is: there’s enough. I still pay attention. Some months I still have to cut back or find new ways to bring money in. I still keep an emergency cushion because the unexpected still happens, two plumbing emergencies in one week recently, and for once I wasn’t even bummed, because the cushion was there.

My relationship with money isn’t a painful one anymore.

So, what’s yours?

How do You Know When to Pull the Plug on Your Marriage?

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The Two Fears That Almost Kept Me Married

When do you decide to give up on a marriage, actually call it quits, and ask for a divorce?

I ask because I honestly don’t know the answer. I never made that decision myself; my ex made it for both of us. Left to my own devices, I probably would have stayed until death do us part. I have a high tolerance for pain, and I’ve always preferred trying to fix things over walking away from them. I still want an answer, even though I’m slowly learning there isn’t a clean one, which is basically why I’m writing this at all. When do you actually call it quits?

Put another way: what’s actually stopping you from initiating a divorce, if part of you wants to?

From what I’ve seen, mostly fear. Two fears in particular tend to do the heaviest lifting: money and the kids.

Let’s take them head-on.

Fear One: You’ll Be Much Worse Off Financially

Being poor was one of my fears too. Combined, my husband and I could live comfortably in an expensive city on one income. Divorced, that math falls apart. I’d need a job, we’d need childcare, we’d need to split assets and fund two households instead of one. Both our standards of living would drop. That was a genuinely depressing thought, enough on its own to keep divorce off the table. I’d rather be unhappy and financially stable than happy and broke, or so I believed at the time.

My divorce happened anyway, and yes, my net worth dropped. My cash flow took a real hit. That brought real anxiety with it. I used to build monthly budgets just to confirm, yet again, that there wasn’t enough coming in to cover what was going out, which only fed the anxiety further, until I finally made the connection that stressing myself into a spiral wasn’t actually accomplishing anything.

Eventually I realized I’d always managed, one way or another. I cut my spending, found ways to bring in more money, made decisions, and kept moving forward in a direction that matched what I wanted for my life. For some people that means earning more. For others, it means spending less. Either way, there’s usually a path through.

Three years out, I can say plainly: being happier on my own is worth far more than what the divorce cost me financially.

Fear Two: The Kids Will Suffer

I’d been the primary caregiver for our two kids, four and six at the time we separated. I genuinely couldn’t picture their dad managing them alone for half their lives. Surely they’d go unfed, unbathed, put to bed late, and laundry would pile up forever. And beyond the logistics: my kids wouldn’t be with me for half their lives. They were four and six. They needed their mother. I needed them. They were, in a lot of ways, my whole purpose.

To be clear, my kids wanted us to stay together. My youngest once cooked up a plan where I’d rent an apartment in the same building as his dad, so we could live down the hall from each other. Adjusting to only having one parent around at a time was hard on them at first. But they adjusted. Honestly, it wasn’t even that different from before; my ex and I had barely occupied the same room together for the two years leading up to our separation anyway. They still have to manage two different sets of house rules, switching gears twice a week, but that’s just life. We all have to manage shifting expectations across different parts of our lives, jobs, family, everything. Kids of divorce just get more practice at it earlier than most.

It was harder on us, the parents, I think. I missed my kids desperately for a full three years after the divorce; I have the blog posts to prove it. It took my mom asking me this past summer, while the kids were away for their two-week stretch with their dad, “Do you miss your kids?” for me to actually notice something had shifted. I said, “No, I don’t miss them,” and then really sat with what I’d just said. The old version of me would have felt like a traitor for saying that out loud, wondering what kind of mother doesn’t miss her kids. Instead, I recognized it for what it actually was: a real milestone, for me, for their dad, and for them.

It took three years to build a life that could actually make me happy while my kids were away, and three years to genuinely trust they’d be fine with their dad. What I’ve come to believe, in that time, is that kids do better with two parents who are both actually capable of caring for them. Yes, it takes more coordination, and the back-and-forth between households is tiring, sometimes a little painful. But now they have two parents who can feed them, get them to school, sign them up for activities, and arrange their own plans. Two parents genuinely involved in their lives. I probably still do more, if I’m honest, but their dad is doing far more than he ever did while we were together. If we’d stayed married, I’d likely still be doing everything, and he’d likely still be on the sidelines. Now I have my own life, and a life as a mom, both. Time for my own things, my own work, my own growth, alongside real trust that my kids are being cared for by someone who loves them. That’s a genuinely good outcome.

It took three years to get here, though. Three years to understand that their dad does love them, and that doing things differently than I would isn’t the same as doing them worse. It’s just different. How do you even judge what good parenting looks like? The best I’ve landed on: a good parent is someone who loves their kids and is genuinely trying to do right by them.

Three years out, the fears that kept me in my marriage turned out to be mostly unfounded. I’m grateful my ex worked through his own version of those same fears and finally ended things. The marriage had run its course. We were done. We’re better for being divorced.

hire yourself

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Hire Yourself

Tax season always brought the same question to mind: why is it still this stressful for so many people, when the software gets easier and cheaper every year?

I’ve seen the full range. Some people have everything to me the day filing opens, organized enough that I could practically just hit enter. Others I’d chase for years before finally filing a decade’s worth of returns in one sitting. In between, every shade of relief and dread you’d expect.

To be clear, I’m not talking about genuinely complicated returns; sometimes hiring a specialist is exactly the right call, so you can focus on what you’re actually good at. I mean the more ordinary case: employees, or people running a simple sole proprietorship, who still can’t bring themselves to sit down and do it.

Most of what stops people comes down to fear, in one form or another. Fear of making a mistake and facing penalties. Fear of having made too much money and owing a lot. Or, on the flip side, fear of discovering they made very little, and reading that as some kind of verdict on themselves rather than just a number. Easier to not look at all.

Then there’s the sheer volume of it. If you run your own business without a system for tracking money in and money out, facing a full year of receipts can feel enormous. I understood that fear well; some of my clients handed me a literal shoebox of receipts every year. Not my favourite kind of work, but it always helped to know I’d get paid for it.

All of that fear adds up to people avoiding a significant part of their financial lives. I’ve always believed that more information puts you in a better position to make good decisions, and burying your head in the sand tends to keep people stuck rather than protect them.

So what actually helps?

If it’s genuinely overwhelming, hiring someone is a reasonable option. Find someone you’re comfortable talking to, and ask them to walk you through what they’re doing as they go. It costs a bit more upfront, but it usually pays off, both in savings and in finally understanding your own numbers well enough to lose the fear around them.

I’m a firm believer in outsourcing what you genuinely can’t or don’t want to do yourself. That’s not a failure; it’s knowing your limits. But there’s a difference between outsourcing the task and outsourcing your understanding of your own financial situation. The first is fine. The second leaves you exactly as afraid of your own numbers as you were before, just with someone else quietly managing that fear for you instead of you managing it yourself.

My favourite suggestion, though: hire yourself. Decide what your own time is worth, sit down, and do the work. Once it’s done and you know what you’re owed, take that money and spend it on something that actually makes you happy. If saving it is what makes you happy, save it. But there’s a good case for putting at least some of it toward an experience you’ll actually remember.

Do that once, and next year’s taxes start looking less like a chore and more like an appointment with a bit of found money at the end of it.

Pay for your own coffee

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Pay for Your Own Coffee

I have friends currently in the dating stage of life, which is fascinating to hear about secondhand, and, being me, the money part catches my attention most.

Nearly every friend I have insists it’s the guy’s job to pay for dinner and drinks. One recently tried to pick up the check anyway and got a “come on, let me be a man” in response; he took it back before she could finish the gesture. Another friend of a friend apparently uses dating to fund her nights out; when money’s tight, she finds someone online willing to take her to dinner. It always works.

I asked around: is there ever a real conversation about the bill? Mostly no. A woman might make a token gesture toward paying, mostly for politeness, but that’s usually where it ends.

What strikes me is that these are all women in their forties, all at least as financially secure as the men they’re dating. This isn’t about need.

So what does this actually do?

One friend went on two dates with someone who paid both times. After the second, she decided they weren’t a match and spent two full days agonizing over how to tell him, instead of sending the simple, honest note she eventually did. She told me it would’ve been so much easier to end it if she hadn’t felt like she owed him something for the forty dollars he’d spent.

A more serious version of this happened to another friend some years back. A guy took her to a fancy dinner, and when the night didn’t end the way he expected, he made his displeasure clear and never contacted her again. She was, fortunately, someone who didn’t let that kind of thing shake her, and her read on it was good riddance. Not everyone comes out of a situation like that as unbothered.

My honest take: men get a lot of leverage for the price of a fairly cheap dinner. Some women consciously use that dynamic to their advantage, which is fair enough, but it still reinforces a pattern that doesn’t really serve anyone in the long run.

This dating-and-paying pattern sets a template, and if the relationship continues, that template often carries forward. Being financially taken care of by someone else shifts the whole balance of power in a relationship. I see a version of this with my own kids: I pay, and I make the decisions.

Do women need to be taken care of? What people actually need in a relationship is to be loved and respected, and assuming upfront that someone can’t take care of herself financially isn’t really either of those things.

I’ve met several widows through my volunteer work preparing taxes for seniors. Almost without exception, they were never the ones making the financial decisions in their households. Learning to manage money for the first time as a senior after losing a spouse is genuinely hard.

The pattern starts small, right at the beginning. Going on a coffee date? Pay for your own coffee.

Same Money, Different Story

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Same Money, Different Story

Retirement takes up a lot of space in our collective consciousness. It’s what we’re all supposedly saving for, and it’s especially loaded right now, when so many people struggle to get by while working full-time.

How are we supposed to save for retirement when we can barely manage the present? Maybe we should all give up. Who needs savings anyway?

That’s a self-fulfilling prophecy if I’ve ever heard one.

Interestingly, plenty of people keep saving anyway. What story are they telling themselves? Maybe they’ve noticed how many impoverished, vulnerable seniors are already out there, and that’s motivation enough. Maybe they still have hope for how things will go. Maybe they’re just hedging their bets.

Whatever story you’re telling yourself about saving right now is quietly shaping how you actually live and spend.

I first noticed how much these stories matter through my volunteer work with the Community Volunteer Income Tax Program. In one year alone, I helped file forty-four returns for low-income seniors, and the highest earner among them made $28,000. During tax season, the line at the Seniors’ Centre wraps around the block. The cutoff to qualify for free filing is earning under thirty thousand dollars a year, and even that’s generous relative to what most people in that line actually bring in. Between Old Age Security and a maxed-out CPP contribution history, someone with no other savings tops out around twenty-five thousand dollars a year. That’s a lot of seniors living on very little, each carrying a different story about how they got there.

One woman I helped had lost her husband years earlier, and with him, the financial security she’d expected to carry her through old age. She’d never worked outside the home. What little she had left, she’d since lent to family, and that money hadn’t come back to her. Every time I saw her, that loss came up again, clearly still the loop playing in her head. And yet she was sharp, put-together, moved quickly for her age, lived somewhere lovely, and had grandchildren who visited. None of that seemed to register next to the story she was telling herself. I could see the worry sitting right on her face.

Another man I helped, in the same building, offered me tea while I worked through his return. We talked about music, hobbies, his dog, who he still tried to walk daily even though walking had gotten harder. He seemed genuinely upbeat.

Financially, there was no real difference between them. Same fixed, minimal means, same basic constraints. But they were living in two completely different stories.

We all find our own way of coping with whatever we’re handed. How we manage it, and the story we tell ourselves about it, shapes how the present actually feels, and how the future unfolds from there.

Most of us will eventually retire, and eventually stop being able to earn. It’s worth planning for. If you want to know where I personally land on it, I’m solidly in the hedging-my-bets camp. It’s a lot easier to stay hopeful when you feel like you have some actual control over your own situation.