How to unfuck my career
My career has been characterized by starting strong right after college (at Microsoft), failing many potentially career-pivotal interviews over the years, making some fairly impactful and memorable work at various startups, but also not having a mentor/coach to guide me, and a bunch of employment gaps from trying to be a founder (and failing), or Covid, or just burning out and needing a break. Also, my career started in Seattle, but then moving back to Toronto in 2011 when the Tech scene wasn't as developed, and the role of PM was also not well understood, so I didn't know what I was doing/supposed to do. Now, after the latest stint at a startup accelerator (and failing), I'm feeling pretty stuck. How do I unfuck this? 1. Clearly, I suck at interviewing. I improved in the Product Sense and Execution (thanks to TryExponent and others), but I'm typically bad at playing myself up when talking about past experience. Any suggestions on how to improve this, and generally at interviewing? 2. I have a fairly horizontal experience (no deep domain knowledge). Does it make sense to specialized in a specific domain, and if so - do I go for startups or scaleups/corporate? 3. What type / size of company should I focus on as a first step to unfucking this? YOE: 8 Highest ever TC achieved ($220 CAD), currently $0 (unemployed) #productmanagement #pm #career
Maybe start with being less hard on yourself. We all fuck up, I bet most of us can find things to feel like a failure about. I'm not saying this to make you feel better 🤣 I just think this state is counter productive. E.g. even when you're clearly looking for solutions in this post it's framed negatively. As for practical advice, why don't you start by understanding what you're good at and what you're interested in? Those two usually go hand in hand, and that's where you'll have a competitive advantage (whether that's a PM role or a different role, I would revisit all the assumptions you're making about what a successful career means to you). And finally, 8 years is not nothing, but it isn't everything either. There's plenty of time to find success.
Thanks for the reply! I really did not intend for this post to sound as if I'm feeling like a failure, and the fact that it did is definitely a much needed wake up call. I think I have a pretty clear idea what I'm good at and what I'm not yet in terms of PM skills. But not sure how about which industry to focus on, and how, and whether it's a good time investment now while searching for a job. Any thoughts on this?
This post feels like me, so OP I'm glad you posted so I could read this response from @Google
If you had the option to work on anything at all, regardless of how you interview what would you want to do? I think the most important thing is to figure out what you love and keep doing it. You may not be always successful but if you keep doing it, and learn from your mistakes and continue on your path, you will eventually be successful. Find out other people who do what you want to do, and talk to them. I don’t have a formal mentor either, and you don’t need one, but when you have a question reach out to the people you think can help you and you will learn from them. Similarly try to help others who could learn from you, there’s always something you are good at. This will improve your confidence a lot
I don't exactly know how to answer that question. Whatever I thought I was interested in, I tried doing via the founder route. Now, I'm rather interested in taking a step back and learning about new problems spaces or technologies or industries while working alongside people who are more knowledgable and smarter than me.
I think you are being really hard on yourself. You were brave enough to try a lot of things and I bet you learnt a lot. If you look at the stats, only 5% startups are successful, but you still learnt a lot through that process. About your next steps, only you can truly figure it out. If it’s tough to pick what kind of work or products you want to focus on, maybe take it a level higher and figure out what matters to you and what you really need. For some people they need the money, some others want status , while others need peace of mind etc. if you can get to that, then it becomes much more easier. Feel free to DM if you would like to chat
You should take contractor roles requiring almost no interviews, giving you opportunity to see the crazy you will work with. If it all works you will be invited to turn permanent.
I've never seen any decent contractor roles in Product.
Curious to learn more about PM contracting - share your experience please
Gladly all the thinks you mentioned can be learned. Failing at your first few startups is okay too. Don't pull yourself down for it. There's no mentor that teaches you everything. Surround yourself with people are who are smart and doing well in the roles that you might want to take up. And find the traits that make them what they are, learn from them.
Pull out
Try boomerang into Microsoft again.
I'm actually seriously considering it. Still have a few friends there that could possibly help getting an interview. How's the hiring freeze/layoff situation there nowadays?
Things are starting to relax.. There are pockets where hiring is happening.. Not much of layoffs, but backfill is stopped so a percent will decrease by normal attrition
Ask yourself what you are willing to focus on and then stick to it for like 4 years. Also ask if PM is right role. Fir interviews connect your experiences together to emphasize a theme and direction.
Asked myself whether a PM career is right for me multiple times. Here's what I arrived at (just yesterday): - The kind of success I would like in life aligns with being successful as a PM, more so than, say, a success as a specialist in engineering. - But, the reality is that it's hasn't been a success, maybe because it's not the right role for me. - So, do I pivot into something I'm not (yet) as excited about while still running the risk of a failure, or do I persevere as PM?
Another route to take is specialize. When you’re a small fish in a big pond in FAANG it can be hard to stand out. But, if you pick an industry you love/ are passionate about and specialize, the tables could turn in your favor
Go back to MS, or literally any other company. You have a good background. Sucks when your startup fails, but it at least shows ownership. Plus you hopefully learned what different failure modes look like, and how to avoid those same mistakes.
Do mocks with people who work at your target companies. Igotanoffer would be a good place to start. They got folks from Google, Meta, Amazon, etc that you can do behavioral interview with, resume review, product design interview and so on.
Thanks! Have you tried it?
Yes! It helped me tremendously to prep and to negotiate with some other companies when I got an offer.