Hey everyone!

It took me under a year to find a job. Literally. I started looking in April 2025, signed an offer in early May 2026, and will start on June 3rd. Let me tell you everything.

Where my head was at when I started looking

I left my job in February 2023 to focus on my health and pregnancy, then went on mat leave, and by April 2025 I was mentally ready to start looking again — hoping I’d find something within a few months and line up daycare for September (September starts are so much easier to find than mid-year spots). I wrote more about the whole experience here. But honestly, when I first opened my laptop to start the search, I was not in great shape (I thought I was but I wasn’t): a more than a year of sleep deprivation, my brain full of baby stuff, the whole world had changed. It took me about a month just to get my bearings, refresh my knowledge, and actually start applying. I had interviews during that time, but looking back, it was night and day compared to this year. I really hit my stride around late November 2025 — especially after my son started daycare in September and I finally had an actual 8-hour “work” day to myself.

The job market

It’s a complete joke compared to when I was job hunting in 2021. Back then I found something in about three months and applied to 21 positions total. This time around, the problems were:

  • Barely any openings.
  • Massive layoffs = massive competition.
  • Companies going back to office, and since most of the ones that exist in Canada are in Toronto, not Vancouver, I was out of luck.
  • The political situation meant a lot of US companies had stopped hiring in Canada altogether.

It was a rough market to be swimming in. I tried everything: applying through connections, cold-applying through LinkedIn, reaching out to people at companies I was interested in. I DMed strangers asking if there were any openings. I even got on a call with a CMO from Silicon Valley to review my resume and LinkedIn and just get some perspective (his take: everything looks fine, the market just sucks). And in the end, the most effective thing was still just applying to open roles on LinkedIn. Oh, and once I had an interview with an AI recruiter. That was a whole thing (no, I did not enjoy it).

The numbers

115 applications total. Here’s how they broke down:

  • 29 auto-rejections with no interview.
  • 13 companies I interviewed with but didn’t move forward with.
  • 6 hired someone else while I was still in their process.
  • 2 I withdrew from after accepting my offer.
  • The rest just ghosted me.
  • 1 offer, which I accepted.

I was way less picky this time than in 2021. Back then I was holding out for exactly the role I wanted. This time I felt the urgency and applied pretty broadly — anything where my skills were even a rough match, not just Product Marketing. The one thing I tried to avoid was pure startups, since I honestly wasn’t sure I could handle the pace with a toddler at home.

What I was doing during my career break

Once my son started daycare, I was really intentional about how I spent my time. Turns out that ended up being huge for my job search - though in the moment I was just doing it for myself, partly to stay sharp, and partly because $2k/month in daycare fees is a pretty strong motivator to be productive.

On top of job searching, I realized I’d missed the AI wave a lot, so I started working through a bunch of courses. Pretty quickly I figured out that courses are kind of useless beyond basic conceptual stuff, so I switched to just building things. First I learned Lovable and threw together a website in like 10 minutes. I had so much to say after being fed up with job searching that the content basically wrote itself. I was genuinely shocked how easy it was. I wanted it on my own domain but didn’t want to pay for Lovable, so I decided to try vibe coding. And that opened a whole rabbit hole… I ended up rebuilding that site from scratch and came up with a cool name returntowork404 because that was how I felt lol. The site itself was quick; the Google Cloud setup took forever, which is how I eventually ended up switching to the Claude API, but that’s a whole other story.

Then a Wealthsimple job posting for an AI Builder role pushed me further. The task was to build a project in a few days and pitch it. I’d been spending so much time on job search admin that I decided to automate the whole thing and built a product that would create a custom resume and cover letter for each role, do company research, interview prep questions, etc. I never launched it publicly (pricing was always the thing I kept putting off), but I used it constantly and it became a key part of my portfolio in interviews. Never got that job, but 1150 people applied I think so yeah..

I also built a mobile game I never launched, a bunch of other random projects, but finished the homepage for this site, and updated the blog design.

I’m bringing all this up because it genuinely changed my job search. Every single interview had some version of “how do you use AI in your work?” and I had a real, specific answer with actual projects to show.

One more thing worth mentioning: from my last job search I still had a prep doc: questions, answers, and notes on key projects I’d worked on. That doc was a lifesaver, because after two years off I genuinely couldn’t remember a lot of the details. Before each interview I’d customize it for the specific company, then load it into Google NotebookLM along with the job posting and a note about who I’d be talking to, and ask it to generate a podcast. Sometimes I’d have it critique my answers, sometimes just riff on the company or role. Then I’d listen on the way to and from daycare drop-off. Genuinely one of the most useful things I did, especially since my memory is still not fully recovered from the sleep deprivation era.

What completely burned me out

Interviews. I was so done. Tired of the nerves, the prep, the smiling, the hoping, the rejection emails. When I finally signed my offer, I sent rejection emails to the other companies I was still in process with with zero regrets. Some of them probably had better comp, but I was so exhausted — and I genuinely liked the company I was joining.

Interview questions I kept getting

A lot of it is the same as in 2021: positioning, GTM, sales enablement, behavioral questions, all still very much present. But some new categories showed up.

AI and the product. Didn’t exist at all five years ago:

  • How are you using AI in your day-to-day PMM work?
  • How do you think about positioning AI products vs traditional SaaS?
  • Where do you see AI changing the PMM role in the next 2 years?
  • Walk me through an example of how you used AI for messaging / research / competitive analysis.
  • How did you use AI when you worked at your previous companies (my personal favorite, because… there was no AI back then lmaooo).

The career gap.

I never waited to be asked, I addressed it proactively in my intro. I was straightforward about it: I left on my own to focus on my health and pregnancy, then raised my kid until I found daycare. After that I was actively searching and building things. I genuinely never got any pushback on this.

Other stuff

Measure success. “How do you measure the success of PMM work?” came up more than ever. My read is that marketing budgets are getting cut and companies want PMMs who can tie their work to actual numbers. I answered honestly: where I had numbers I gave them, where I didn’t I talked through my approach and what signals I was watching.

Behavioral. Tell me about a time when… Constant. Every company, every stage, some version of a messy-situation-at-work story.

How it ended

I got through the full interview loop at a local company, mostly remote, with one in-office day a month (please let that not change). I think that’s basically ideal. I liked the manager, I liked the team. I’m terrified, but hoping I’ll hit the ground running. I’ve never done this whole working-in-PMM-while-being-a-mom thing simultaneously, so this is genuinely new territory. Trying to figure out how to fit in the gym, cooking, real time with my kid, and doing good work without completely losing it.

If you’re in the search right now

A few things I took away from this year (nothing revolutionary, but):

  • Build something, especially if you have a career gap. Not for the portfolio but for keeping your brain active and having real things to talk about in interviews. AI has dramatically lowered (and somehow also raised) the bar: you can have something working in an evening.
  • Stop agonizing over cover letters. In 2021 I spent hours on each one. In 2026 I started spending minutes, and after building my own tool, basically zero time. The results were no different.
  • Pay attention to your own state. Job searching is a marathon. If you’re running on empty — take a break. How you show up to an interview matters. (That said, the final interview for the job I got the offer from I was genuinely a mess: sick, dealing with a separate medical emergency, just wanted to be horizontal. And somehow I passed it.)
  • It’s not you. It’s the market.

Thanks for reading. Wish me luck!