Switching careers is hard. Do it anyways.

It’s not easy to make a career change. For most people, the anticipation of pain that’ll come from the inevitable sequence of rejections is enough to hold them back from really trying. I believe that most people only dip their toes in the water and apply to a few jobs when they are really frustrated with their current situation. But most of the time, they’ll convince themselves that things are fine. 

In the short term, this might be a decent strategy to get through the next bonus cycle. However, in the long term, you won’t win. 

Think about it. How can you grow at the rate that you are capable of (both personally and professionally) if you aren’t doing something you are excited about and can learn from?

That’s why I root for people who commit to pull themselves out of their current situation and into something better. They understand that it’s worth it to experience the short term pain in exchange for long term gains. 

I’m especially happy to lend a hand when they happen to be transitioning into Product Management because I went through that same journey too. 

As a matter of fact, in just the past few weeks, I had coffee with four different people who are actively making the move. During each chat, people seemed genuinely surprised that I was able to expand on the problems they were facing and offer actionable tools and tips they could try out immediately. 

What they don't realize is that the obstacles they are facing are largely the same ones I faced too!

While I was able to help those four people out, I wanted to expand on the three most common obstacles that keep coming up through coffee chats in hopes that it can help other aspiring PM’s in the midst of their own change.

Obstacle #1: telling your story in a compelling way

I think that most people wing it when they tell their story of why they want to change careers. That’s because they don’t want to sound scripted. For a while, this is how I tried to do it too. While some conversations went smoothly, others were the equivalent to slow motion train wrecks! It’s only when I realized that I was throwing away potentially great opportunities due to my lack of preparation that I pivoted away from the “just wing it” strategy.

The more I researched, the more I appreciated how much effort it takes (even for top performers) to sound natural. This is how they are able to deliver maximum impact. As an example, check out this break down video from NerdWriter on how Louis CK tells a joke. Every single word, or pause, or point of emphasis is there for a specific reason.

By no means am I suggesting that you need to have your story down the way he does.

But, by putting in the work to write down your story in advance (and then recording yourself practicing it over and over again), the odds of telling your story in a compelling way will significantly improve.

Obstacle #2: don’t be a “taker” at networking events

Based on the people I meet at networking events, I’d venture to guess that 70% of them are there because they desperately NEED a new job.

If you can stand out from the crowd, networking events can be an effective way to get an inside track to meet recruiters and hiring managers. If you can’t, then they become a frustrating time sink.

Here is the mistake I see most people make. They adopt a “taker” mentality. If they sense you have something of value they could get, they make it abundantly clear they are trying to get it. If they sense you don’t have anything they want (ie. you are also looking for a job), they tune out and start scanning the room for other people to talk to. 

Here’s what I did instead. I adopted a “giver” mentality. In each interaction, I tried to think of ways I could add some incremental value for the other person. And I’m not talking about large scale things either. It could be something small such as introducing them to another person at the event because they had something in common, or sending an article to them because it was something I thought would help them out.

When I did this, the value that came back to me significantly increased compared to when I operated from a “taker” mindset. I scored more coffee chats, got higher quality introductions, and overall, had a much more pleasant experience.

To learn more, check out Adam Grant’s TED talk about the science behind givers and takers!

Obstacle #3: “we’re looking for someone with more experience” 

The evergreen problem is that companies don't want to take a chance on you unless you have direct and relevant experience. And when you don’t have a Product Manager title, it can feel like a chicken-and-egg problem when you repeatedly get rejected for this reason.

Even after I got past the first two obstacles (above), I could still sense hesitation from recruiters and hiring managers. Even though I would make it through multiple rounds of interviews, they would ultimately go with another candidate with “more experience”. 

What they were saying between the lines was that they didn’t think I could do the job. And I couldn’t fault them either since I didn’t have a portfolio or a track record to prove otherwise.

I knew that I had a few options to deal with this obstacle though. First, I could try to go down the verbal Jedi route and pull out proof points from previous jobs where I excelled and then try to link that past performance with future potential. Or, I could work on some projects on my own as leverage to sway the hiring team to take a chance on me.

While the first option was easier, it is also the option that most people lean on. By doing this, aspiring Product Managers are implicitly stating, “give me a chance, and then I’ll prove I have what it takes”. 

I decided to go with the second option and adopted a better mindset of, “I’ll prove I have what it takes, so that you’ll want to take a chance on me”. 

How did I do this? I proactively beefed up my dilapidated coding and non-existent design skills. I knew that in the near future, when I got into a Product role, my success would be correlated with my ability to work closely with Engineers and Designers. And to do that, I would need to speak their respective languages.

But even more pressing, I knew that through the interview process, I would be meeting with Engineering and Design managers who would ultimately cast a vote on me. And the more I could do to convince them I had what it took, the better off I’d be.

Here are the two online courses I took and really enjoyed. The best part is, both courses assume you do not have prior experience and start off with the basics.

• Coding: The web developer bootcamp
• Design: Mobile app design in Sketch 3 - UX and UI Design from Scratch

Conclusion

Changing careers is hard. There are going to be failures along the way. Don’t beat yourself up about it. But do take some time to think about how you can accelerate the transition by crafting your story, learning how to network, and convincing others that you can contribute to the team on day 1.

If you have any questions, leave a comment below and let's discuss!