Toronto likes to pretend it’s building for the future. Glass towers continue to rise though not as rapidly as they did in the 2010s. Density targets are kind of met in some areas of the city while other neighbourhoods scream about density like they’ve been tasered. Transit lines inch forward, slowly, encouraging runners to do a PB. On paper, it looks like progress, I guess. Though it’s uneven.

I’ve talked about how investor condos plague this city and that they were never meant for a person to live in community, aka, having the room to entertain. That means going somewhere else, the third space.

Sociologist Ray Oldenburg coined the term “third place” to describe social spaces outside home (first place) and work (second place): cafés, parks, pubs, and plazas where community happens informally.

Thing is, when your home is too small to host, you become dependent on third spaces. In Toronto, many of these now come with rules like time-limited seating, purchase requirements (spending money), security enforcement (food courts), or design that discourages lingering.

Yeah, we could hang out in parks but -18 degrees celsius with a lovely -27 degrees with the windchill. Absolutely not.

That got me thinking, why does Toronto want us, especially those who don’t have a ton of disposable income, to be lonely? You have to pay to have community, like a subscription or streaming service. Gross.

Toronto’s housing stock has an ongoing problem apart from not having enough stock. There are high-rise condo towers on one end and detached houses on the other. What’s largely still absent is the missing middle of duplexes, fourplexes, (which aren’t four stories, Doug Ford) courtyard apartments, and small walk-ups that naturally foster community and offer attainable ownership.

For solo earners, the missing middle is often the only realistic path to ownership that isn’t a shoebox in the sky. Without it, singles are pushed into:

• precarious rentals owned by mercenary rental corporations

• investor-driven condo stock

• social isolation in vertical housing not designed for permanence.

Ontario has begun allowing more multiplexes (despite not meeting housing goals) but decades of restrictive zoning created a market distortion. Today, some very small condos sit unsold or rent for less than projected because the product is small, shitty and doesn’t match how people actually live.

That means having third spaces that are affordable to meet. We’re really great at that in summer but winter? Oh boy. Summer has all the parks, the islands, parkettes and courtyards. All mostly free and affordable.

Winter is where this design failure becomes impossible to ignore. For nearly five to six months of the year, Toronto’s most generous third spaces are functionally unusable unless you’re dressed for an Arctic expedition and willing to let the wind hurt your face, just meeting in the park sounds miserable and like your friends hate you.

If your condo can’t host and the outdoors is hostile, you’re pushed indoors into places that expect you to buy something, leave after 60–90 minutes, or justify your presence by spending more.

Winter turns third spaces from a nice social bonus into a paid necessity. For single people, especially those without much disposable income, that means community isn’t just hard to find, it’s literally gated by temperature, how warmly you’re dressed and a debit or credit card.

Ok, rant over. Let’s get practical. Should we treat third spaces and the missing middle as housing infrastructure, not nice-to-have amenities?

That means funding libraries, parks, and community centres as year-round social living rooms. (I love libraries, can you tell?) Designing indoor public seating where no purchase is required; approving housing that includes real tables, real second chairs, and layouts meant for hosting; and legalizing duplexes, fourplexes, and courtyard apartments in every neighbourhood so singles can build community where they live. This is being done, absolutely, but not consistently across the city and not enough of the right type of stock is being built.

Toronto is a city and I really think it has a civic obligation to expand public space. Otherwise, the city isn’t building density, it’s engineering loneliness. And we wonder why there’s a loneliness epidemic?

A ton of finance surveys and news. Also, Valentine’s Day isn’t that romantic in 2026.

Inflation and the cost of living is affecting dating. A new survey from the BMO Real Financial Progress Index found that nearly half (49%) of single Canadians don’t think dating is financially worth it. Those who are still dating have gone of fewer or less expensive dates. Bet they aren’t going to restaurants.

I know that this newsletter focuses on finance for single people but yikes with some of these releases.

Money Mentors also released its 2026 Love and Money Benchmark Survey. It found that nearly one in seven Canadians say their financial situation would make them consider breaking up with their partner.

Some of the key findings include:

• 17% of Canadians say financial stress has made them consider ending a relationship

• 25% say financial factors negatively affected their relationship or dating life in the past year

• 52% of Canadians in a relationship report personal impacts after arguing about money, including anxiety, depression, and poor sleep

• 11% admit to lying to their partner about their financial situation to avoid conflict

I’m sorry, none of that is very romantic. Hell, Galentine is also affected as 47% Canadians are cutting back on eating out according to Koho.

Re-upping this from 2024 as it’s still relevant.

I’m not going to lie to you and say I don’t worry when I see layoff news and the difficulty in finding a job. Being single and working as a contract, gig worker or freelancer has its pros and cons.

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On one hand, you have the freedom to set your own schedule and work on projects you love and there is no real ceiling on how much money you can earn, only on how much you really want to work, burn out and cry because hustle/grind culture gets toxic.

It also makes you resilient, which simultaneously is good and sucks. I think that single people are very resilient just by living in a society that still caters to couples but single contract and gig workers have that extra bit of resilience. So high praises to everyone.

On the other hand, without a steady paycheque or a partner to share responsibilities, things get scary when you lose a client or a contract isn’t renewed because bills and retirement don’t care if you aren’t working. They need to be paid. While I know I have options including my family or living on lines of credit, I really, really don’t want to be put in that position, so here are some things I’m doing. Some are things I can control, others just give me a sense of control.

Also, can I quickly address the Washington Post layoffs and the comments that the journalists can just do Substack? A lot of people do not make a living wage from their newsletters. Plus there are the vital parts of publishing that journalists need like editors and legal support. You think investigative reporters are out there without legal support when the subjects decide to unleash their lawyers?

Get your finances in order

Budgeting basics

This is the obvious one and yes, I know we can’t budget our way out of things like the housing crisis or pay discrepancies for marginalized groups but when your income varies month to month, having a budget is crucial. That’s because you’ll know where you spend your money. It’s that ‘give every dollar a job’ as said by certified financial planner Jackie Porter. 

I usually have a decent idea of my monthly earnings so once I have that, I break down my budget in the following: 

Bills: maintenance fees, food, hydro, insurance, property taxes and special assessments (at $100 a month for those two so by the time those bills arrive, I’ve saved up the money painlessly and pay them off in full.) As an fyi, my property taxes will go up another 2-3% in 2026 which is again, less than I expected.

Savings: RRSP, TFSA, cash savings for vacations. And yes, I automate everything as much as possible. It makes it easier for me to save and budget.

Emergency fund

An emergency or as I’ve read recently, a comfort fund is a must-have. The usual is to save enough to cover three to six months of expenses but honestly, start with a month. Save up what you need to pay bills for a month so you at least have a little bit of breathing room. 

The easiest way (and I know that’s relative so bear with me) is to look at what you earn and what you spend on the necessities in a month, divide it by the number of months you want to do it in, then set up automatic transfers to a savings account to make this easier. This fund will be your safety net when work is slow or unexpected expenses pop up.

I wrote about how to actually save for an emergency account here.

Taxes

Taxes can be a headache for freelancers, but staying on top of them is essential. Set aside a portion of each payment you receive for taxes— and this is important put it in a completely separate account from your chequing. Do not get a debit card for it.

Multiple income streams

Don’t rely on just one client or type of gig. Diversify your income by taking on different projects. This not only makes your finances more stable but also keeps your work interesting. Again, I say this with caveats as this is something not everyone can do due to physical, mental and other reasons. Also, it’s not ideal as the solution for trying to live shouldn’t be to work a gazillion hours a week.

Build a support network

Freelancer friends

Working alone doesn’t mean you have to feel isolated. Connect with other freelancers through online groups, social media, and local meetups. They can offer advice, share job leads, and provide moral support and practical advice like what to take out of contracts (I see you, liability clauses - no, you don’t pay me enough to take on full liability).

You don’t have to be in the same industry, either. I think it’s better to have friends outside of your industry otherwise you just end up complaining about the same things over and over again. (Venting is good, constantly meeting up to complain is not.) Plus, they can provide a different perspective on an issue.

Keep in touch with your friends and family. Share your successes and challenges with them which can make you feel less alone. 

Join professional groups

Professional organizations related to your field can be invaluable. They offer resources, training, and networking opportunities that can help you grow your business. A lot of the time the fees are tax-deductible.

Prioritize self-care

Set a routine

I’m not the best at this, so this is going to sound hypocritical. I am, however, trying to be better about it. I keep regular working hours, between 9-5, take breaks, and make time for meals and exercise. Yes, I will occasionally work on the weekends but try to keep it to two-three hours. (ha!). Though I did quit a gig that tried to set me up to fail and wanted me to work the entire weekend.

Create boundaries

Working from home can blur the lines between work and personal life. Designate a specific area for work and set clear boundaries for when work starts and ends. Turn off work notifications after hours to help you unwind. I live in a one-bedroom condo so my dining table has been my desk for more than a decade. I’ve just gotten very good at ignoring it outside of working hours. 

Enjoy your hobbies

I’ve been taking Spanish lessons for the last year with an actual teacher, not just Duolingo and have reached the ‘I have enough knowledge to sound vaguely comprehensible’ stage. Update: gotten pretty good with reading, still need to build up my confidence to actually talk.

Also, having hobbies stops you from making your work your entire personality. That way, you aren’t your work or job so should something happen, you won’t feel that you’ve lost yourself. You have lost your job or a client but you’re still you.

Thank you to everyone who reserved a ticket to the launch party. It sold out, which is exciting. I’ll see you there.