By Harold Phillips | June 2026
The startup folded on a Tuesday in November.
I remember that detail because November in Toronto has a specific quality of grey that makes everything feel more final than it is. Cold but not yet winter. Dead leaves stuck to wet pavement. The kind of month where you get bad news and it stays with you longer than it deserves to.
Our CEO called a company-wide meeting at 10 AM, which in a 22-person startup is the kind of meeting everyone recognizes immediately as not being a routine check-in. He was good about it, actually. Straightforward. Funding had dried up. The runway was gone. We had two weeks of pay coming, severance if the lawyers allowed it, references from anyone who wanted them. He thanked us. People cried. I didn't, but I thought about it on the subway home.
I was 27.
What I hadn't fully reckoned with (and I'm slightly embarrassed about this in retrospect) was how thin my savings were. I'd been at the startup for about two years by then, long enough to feel settled but not long enough to have built much of a cushion. I was paying rent in a shared apartment east of the Danforth, I had a few hundred bucks in a savings account, and I had my TFSA with maybe $4,000 in it that I'd been meaning to do something intentional with for two years. That was it. That was the whole buffer.
The advice you always hear is "three to six months of expenses." I'd heard it. I'd nodded at it. I'd never actually run the math on what three months of my expenses actually came to.
I ran the math that Tuesday afternoon.
It was more than I had.
What two months of unemployment actually looks like
I was unemployed from that November until mid-January. About two months, give or take. On paper, that's a short gap. In practice, job-searching through December in tech is a miserable experience because approximately no one is making hiring decisions between mid-December and the second week of January. You're sending applications into silence. You're having coffee meetings with people who genuinely want to help but are themselves wrapped up in Q4 chaos. You're doing everything right and getting nothing back, and the calendar is the enemy.
I spent money I didn't have. Not irresponsibly. I wasn't going out or buying things I didn't need. I was just paying rent and eating and taking the TTC to whatever informational interview I'd managed to schedule. Normal life expenses, with no income coming in. My savings account hit zero before the New Year. I put groceries on my credit card more than once. I borrowed $500 from my parents in January and felt genuinely awful about it. Not because they made me feel bad (they didn't), but because I'd been an adult with a career for several years and I'd somehow let myself reach a position where a two-month gap could do this to me.
It wasn't a catastrophe. I know that. I found a contract role in late January, something to bridge things while I kept looking, and that led eventually to the job I still have now. But the feeling of watching a savings account drain in real time, that specific anxiety of doing the math in your head every time you tap your card, that didn't leave me quickly.
Honestly, it took a couple of years before I stopped flinching at unexpected expenses.
So when I rebuilt my finances after 2019, I didn't just follow the standard advice. The three-to-six-month range: I'm genuinely not sure it's wrong for most people. But for me, the experience of that winter made the low end of the range feel like wishful thinking. Three months sounds fine until you're job-searching through December and January and the calendar is eating a month and a half of your "timeline."
I keep closer to eight months now. That's my actual target, and it's more than most people would say you need.
Here's the thing: I don't think eight months is the right number for everyone. Maybe it's too conservative. My job is pretty stable, my skills are transferable, and I don't have dependants or a mortgage. Someone in a more precarious industry, or someone supporting a family, might need more. Someone with a genuinely in-demand specialty and a short typical job-search cycle might be fine with four months. I'm not trying to prescribe a number. I'm just telling you that mine is eight, and I sleep significantly better because of it, and that matters to me in a way that's hard to put a dollar value on.
Where it actually lives
The fund is in a HISA. Right now I use Wealthsimple's cash account, which has been paying a reasonably competitive rate compared to the big banks (I have a full review here if you want the details). It's not invested. This is a deliberate choice that I've gotten mild pushback on from people who think I'm leaving returns on the table.
Maybe. Probably, if we're being honest about the math.
But an emergency fund has one job: it has to be there. Immediately, no-questions-asked, no-market-timing-required, there. If your emergency fund is in an index fund and the market drops 30% the same month your company announces layoffs (and those two events are correlated, as it turns out, because recessions tend to do both at once), you've just discovered that your emergency fund was actually an investment account with a stressful exit clause.
I'm not anti-investing. My TFSA has actual investments in it. I try to put money away every month toward actual long-term goals. I wrote about how TFSAs work from my perspective over here if you want my take on how I think about the two accounts as different tools. The short version is: my TFSA is where my invested money lives, and my emergency fund is where my "the world is falling apart" money lives, and I deliberately do not mix them.
Keeping them separate is, for me anyway, a psychological thing as much as a financial one. When I look at my HISA balance and it reads eight months of expenses, something in my nervous system relaxes. That reaction has no rational basis beyond the winter of 2018.
The number I actually use
I based my target on my real monthly expenses, not some round number I found on a personal finance website. If you want to see how I calculated what a month of expenses actually looks like, I went through the whole breakdown in my spending post. That's the starting point I'd suggest if you're trying to figure out what your own number should be.
Once you have an honest monthly number, multiply it by however many months lets you sleep. If you've never been laid off, three to four months might genuinely be enough. If you work in a cyclical industry, or you've been through a gap before, maybe you go higher. If you have a partner with stable income and your household can absorb one income dropping to zero for a few months, the math changes again.
What I'd push back on is treating the standard advice as a ceiling rather than a floor. "Three to six months" is the starting point of the conversation, not the final answer. The personal finance industry loves presenting these round-number guidelines as though they come from somewhere authoritative, but they're just heuristics. Rough estimates of what's probably fine for most people under average circumstances. Your circumstances aren't average. Mine aren't either.
There's one more thing I want to say about that winter, something I don't think personal finance writing talks about enough.
The hardest part wasn't the money. It was the uncertainty. Not knowing how long it would last. Not knowing if the career I'd been building was actually portable, or whether the startup experience would read well on a resume, or whether I'd have to move back to Barrie and figure things out from there. The money was the symptom. The anxiety lived underneath it.
Having a real cushion now doesn't eliminate that anxiety. But it changes the texture of it. It transforms "I can't afford for this to happen" into "if this happens, I have time to handle it well." That gap matters. It's the difference between reacting in a panic and making a real decision.
I started building the fund properly in 2019. I've built it up, drawn from it a couple of times for actual emergencies (one car repair that wasn't my car but was absolutely my problem, one medical thing), and refilled it both times. It's the most boring part of my financial picture. It doesn't compound impressively. It doesn't have a referral program.
But every November when the city turns grey and the leaves come down, I check the balance and I feel better.
That's worth something.
Opinions are my own. If I mention a service I use, there might be a referral link — you'll always see a note about it.