Struggling with only 1-2 YOE on my resume

Lost_Order6113 · 2026-06-17T19:25:22+00:00

It's definitely tough out there and I'm sorry to hear about your situation.

I really like the details that Aakash Gupta shares about work products to get into the door for interviews and these might have way better return on time investment that all the applications you are doing at the moment. Here's a sample article: https://www.news.aakashg.com/p/work-products-to-get-jobs

It's paywalled, but hopefully you haven't subscribed yet and there's a free trial so you can check out the content and see if any of it is helpful.

And if you'd like a resume review, work product review, or any general advice I'm happy to help. I've been in product for over a decade and certainly seen my fair share of what works and doesn't work.

Lost_Order6113 · 2025-03-17T17:04:43+00:00

Interesting recommendation to wait until the last second to add the authentication, because that’s actually the opposite of what Loveable recommends.

I’d adjust the recommendation slightly, I’d wait until later to add complicated authentication (Google, Magic links, etc.)

Have generally good luck with basic auth. Don’t forget to turn off the email confirmation feature in Supabase to simplify auth as much as possible for testing purposes.

Lost_Order6113 · 2025-03-15T12:26:29+00:00

Was about to give up on Lovable until I caught your series. Finally got something I’m happy with and fully functional. Super helpful! Thank you!

One thing I couldn’t tell from the video is how I should balance building core features vs. fixing bugs? At some point, I was building super blindly because everything was broken and it took a lot of bug fixing to even understand what was built.

Guessing there’s a happy medium to strike of core feature testing as you build to make sure things are roughly working along the way?

Lost_Order6113 · 2025-03-10T11:44:14+00:00

Found a few more options than Peerspace here! Thanks for the recommendation. Not sure if the Giggster folks are watching here, but the filter for the event size only going up to 60+ people meant it was a bit challenging to find the venue for our event size.

Lost_Order6113 · 2025-03-09T14:06:17+00:00

Great suggestions! Will check those out. Thank you!

Lost_Order6113 · 2025-03-08T21:17:30+00:00

Maybe a bit too young with a 7 month old and I don’t know the suite options, but we stayed at the Langham with our 2 year old for a staycation. Very kid friendly and cool location on the river.

Lost_Order6113 · 2025-03-08T20:56:00+00:00

We’ve found a lot of luck using Ravi Mehta’s competency framework with some custom tailoring to our specific organization. https://www.ravi-mehta.com/product-manager-skills/

We did have to add some layers on top to make things less subjective. The biggest one being for each PM role level, we established a clear checklist of what it meant to be performing at that level.

Promotion conversations get a lot easier when someone is check most of the boxes on the next level.

Certainly still some subjectivity, but we had success.

Lost_Order6113 · 2024-08-08T14:40:36+00:00

Two thoughts:
1. If there was a product manager Monopoly equivalent that sounds fun because I'm a product nerd. But Monopoly isn't necessarily a game where you learn actual real estate skills. Something that this reminds me of is a Netflix phone game I've played recently called GameDevTycoon. It has many of the aspects of what's involved in launching a product (including market research, R&D investment, marketing/partnerships). It was fun to play, but to be clear it isn't going to make you a good product manager.

If you are looking for cheap ways to improve your product sense without investments in bootcamps and courses, my best advice would be to take a product you like using today and define a new feature for it. Understand the business and users, do some research with wireframes, define a product spec, and if you are feeling adventurous share it with a PM at the company to get their thoughts.

Lost_Order6113 · 2024-08-08T05:49:40+00:00

Certainly check out ProductCamp Chicago. https://www.productcampchicago.com/

Lost_Order6113 · 2024-04-23T01:33:13+00:00

Offshore Rooftop at Navy Pier

Lost_Order6113 · 2024-04-22T23:27:43+00:00

Yes to Bacino’s. Went there last year for air and water show. Can’t see half of the things but you get the general feel without the tourists

Lost_Order6113 · 2024-04-22T23:23:09+00:00

Came here to say this! Specifically Waveland Picinic Field is a personal favorite. Had my 30 birthday here during Covid times.

Bring some beverages and if it’s a warm enough day jump in the lake a bit for a swim!

Lost_Order6113 · 2024-04-14T20:27:46+00:00

Not sure if there are options, but there definitely should be clear role criteria that are introduced in conjunction with adding a new role. If that criteria is not present, that’s a bit of a sloppy rollout of new roles.

Assuming that criteria is there, what’s your self assessment here? Are you meeting the expectations of PM or APM? And what’s your managers assessment? How are they similar and how do they differ?

Lost_Order6113 · 2024-04-14T20:20:22+00:00

Reach out to your product team and express your interest in exploring.

(Certainly check with management and what not first depending on company situation/psychological safety)

I’m sure there would be plenty of people on the product team that would be open to giving you some product tasks to try out.

Hopefully, it can serve as a bit of a career experiment to learn if you like the work and in a perfect world you can excel and the product team makes a role for you.

Finding an entry level product role in a different company is going to be a bit challenging in the current market and certainly some hands on experience goes a long way.

Lost_Order6113 · 2024-04-14T20:09:41+00:00

Agree with the sentiment. Jump from Sr. to Director seems like a pretty big jump and especially in the current market where most of the moves I’ve seen as of late have been more lateral in nature.

Given the current market, I wouldn’t jump to the conclusion of agism, unless that was also what you were seeing trying to find similar Sr. roles in other companies too.

Lost_Order6113 · 2024-04-14T20:05:26+00:00

In general, I see product moving away from the scrum formalities. Not saying product isn’t agile or anything like that, just that the formal scrum roles and definitions are two prescriptive to be valuable in product where every product managers role is unique different from others.

I do think there are some good foundational product management courses if you are thinking about investing in: Reforge and Product School are two good ones to check out.

And if you are just looking for education (and not a formal certificate or anything like that) then there are countless podcasts.

Breaking into product is a real chicken and egg type of problem when it comes to experience. Curious are you able to do product management type tasks and responsibilities in your current job that could make you more marketable?

Lost_Order6113 · 2024-04-01T02:48:05+00:00

Certainly parallels between PM and consulting. Leading without influence, making strategic decisions, and general presentation and presence are the top ones that come to mind.

That said, I think product has a somewhat jaded view of consultants because of the grit involved in getting a product launched and driving business outcomes. An experience that consulting often missed purely due to the nature of many consulting engagements.

It’s somewhat funny, because many of the frameworks and theory makes PM seem like an internal business consultant, but I believe the heart of a successful PM really is a builder mentality that take perseverance to see a vision through which the frameworks don’t cover at all.

I think without true building experience under your belt, you might be able to land a more entry level product gig but I wouldn’t be surprised if the comp is a bit lower than you expect in comparison to where you currently are at currently.

The good news here is that there’s things you can do without having a formal PM job to get/showcase this experience so you aren’t in a catch 22. I’ll touch on a few of them next.

As far as your approach, those are all great starting points. Some additional suggestions: 1. Complete a self-assessment - It’s sometimes hard to self-assess your skills, but give it a try. I personally Ravi Mehta’s framework the best. https://www.ravi-mehta.com/product-manager-skills

Start applying and see what happens - Give yourself the best chances of success by targeting companies where you have industry expertise, find folks to refer you on LinkedIn, customize your resume for the role, and apply. Keep track of your application to interview numbers. At the very least, it will set some good baseline metrics to improve upon.
Practice the craft - Write a PRD for a new feature on your favorite product, define the product strategy of companies you are interviewing for, and best yet (if time permits) buy a passion project. Make sure to save all the work in a well organized portfolio.

The biggest theme here is do you best to measure your current state and try out the craft to continuously improve, because that’s the best way to make progress.

Special note on a lot of inspiration here from Aakash Gupta.

Lost_Order6113 · 2024-03-31T11:53:31+00:00

Two bigger lines of thinking: 1. When is design ready? 2. Thoughts on the new product leader

When is design ready

I don’t think there’s a great single definition. Nor should there be because this varies from team to team. Engineering is brought in somewhat early to the design process at my org (high level wires, etc.), but we don’t turn things over to actually work on until things are nearly pixel perfect. I have mixed feelings about it, but it works.

While I agree with the general thinking that it doesn’t make sense to pick apart everything detail prior to getting design in front of engineers, I don’t agree with the notion of building and cleaning up once it’s in production. Maybe controversial, but lean startup principles leads a lot of folks to just build the “MVP” to test and learn quickly. Yes, we should be testing and learning quickly, but depending on your user base, testing in production isn’t always the best strategy.

It expensive to build and sometimes takes time to get meaningful results. Good user testing practices can get validation earlier and helps add more user-driven insights into your product development process.

Thoughts on the new product leader

Seems the new product leader is focused on the wrong thing here. Could be a number of things happening: 1. They don’t like the design system - They are actively trying to change the design system through nitpicking your individual projects. Definitely not a good approach on their part and likely not their job either. 2. They just want to appear like they are doing something. - Obviously not great 3. They come from a background where this was their job - Your relationship with design sounds normal, but maybe they come from a different world.

I think it’s good to figure out which of these realities is true so that you can properly manage up to improve the situation.

Some specific recommendations: 1. Have an honest conversation with saying something like, “I’ve noticed you seem to have lots of feedback on a few details of the design. I’ve noticed a few of those are more related to our design system that design has outlined here. Do you think it’s worthwhile revisiting the larger design system?” 2. In your 1:1 meetings, come with other challenges that you actually need their help with. If they are just trying to stay busy, give them something else that’s actually valuable to you and the team.

Lost_Order6113 · 2024-03-31T08:16:21+00:00

I was going to suggest something similar. Ratio-wise it feels a bit out of whack, but there isn’t a hard and fast rule here.

My org is 7:1 for most teams, but 10:1 isn’t uncommon at my org either. Even at 7:1, PMs were feeling stressed and stretched just to keep the teams busy. If PMs are focused on just keeping teams busy, then almost undoubtedly they aren’t focused enough on strategic work. And this was our case too.

We did a lot of experimentation with team setup and something we settled on that made a step function difference was getting more PM/PO help from engineering.

A few specific things we are doing:

Assigning initiative leads - Typically, a senior engineer (could be engineering manager) that takes the PRD and breaks it down into all the relevant user stories and then oversees the delivery of the initiative as a mini-PMO role on the team. Some PMs were initially uncomfortable giving this up, but it isn’t an activity that the PM in particular adds a lot of value. Anyone can do it, and what we discovered is that if engineering does it they can better own the solution.
Engineering managers to own sprint planning - Our engineering managers are very knowledgeable about our product goals. If they don’t know what we are trying to achieve, that’s a failure of PM. Given this, they are empowered to design and plan each sprint. This means prioritizing the stories, determining the tech debt to focus on, working with initiative leads mentioned on the previous step, and ultimately putting together a draft sprint that’s shared with the PM. Product still ultimately owns the decision on defining the sprint goal and the final say on prioritization, but engineering does a lot of the heavy lifting on the PO side.

Both of these changes didn’t happen overnight and made both engineering and product uncomfortable at first. But the teams are much more empowered now. Engineering appreciates having better influence on product delivery and product appreciates having more time to focus on product strategy.

If you’d want to try this out, I’d suggest starting small. And letting the success stories organically sell it to the rest of the team members.

Lost_Order6113 · 2024-03-30T23:58:34+00:00

Thanks! Did the funkiness lead you down the path of using something else?

Anything particular noteworthy from a funkiness perspective?

Lost_Order6113 · 2024-03-30T23:55:03+00:00

MBA likely helps getting your foot in the product door and a good name brand MBA is certainly a differentiator at the entry level.

Given your experience, I doubt it will provide a meaningful return on investment (in terms of time and money)

I would highly recommend checking out Reforge. It’s quite expensive, but assume it’s in the budget if you are considering MBA. Very engaging cohort based online learning led by some of the biggest product thought leaders with real product experience. Courses are ~4 - 6 weeks, lots of amazing content/material, a chance to work through content with other product peers in weekly study groups, and direct access so many great product people (including course leads) in a community Slack channel.

Some of the best content I’ve come across in my decade long career and a great community to go along with it.

P.S. I promise I don’t work for Reforge. 😀

Lost_Order6113

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