Break into tech chess game

How To Break Into Tech In Your 30s – The Not-So-Secret Playbook

Like Po learned, the secret ingredient in the secret ingredient soup is…there’s no secret ingredient. It’s just you! Sorry for the big letdown, but deep down you knew that, right? In this article, I’ll share the playbook I used to break into tech – borrowing from what I learned in breaking into investment banking. Warning: it’s all hustle and grind (which many 2x-ers are already familiar with). So if you’re ready to work smart and hard (in that order), then breaking into tech and later 2x-ing should be an accomplishable feat. Just start.

So why did I leave the “lucrative” world of investment banking? It was the old classic breakup line: “it’s not you, it’s me.” I just wasn’t wired for banking. I couldn’t take orders well or sit in a suit and tie for 16 hours. Moreover, I wasn’t willing to make the time-for-money tradeoff at the break-neck pace of banking. That’s when I decided to break into tech. In my opinion, if you cared about your family, you can break into tech and 2x Overemployed to financial freedom.

Kung Fu Panda by Dreamworks Animation

Side note: I’ve purposely kept my background vague. Perhaps one day I will do a grand reveal. Then again, perhaps not.

Systems Win Championships (and let you break into tech): LinkedIn, Excel, And A Good Ole Reliable Phone and Internet

Midway through life, I realized I had developed a system to meet my personal financial goals but did not have a system for managing my career. I was in my mid-30s and still meandering. I went from a low-paying entry job to an average-paying white-collar job. At that critical juncture, with kids in tow, I decided to shape up or end up bagging groceries at old age like a scene out of the movie The Shawshank Redemption. So, I started plotting Pinky and the Brain style.

How to reverse engineer LinkedIn backgrounds and look like you belong

Humans, and especially recruiters, hiring managers, and HR, are incredibly linear when it comes to hiring. No one likes to stray away from the pack and take risks on an unproven candidate. The pressure and incentives are rigged towards hiring someone who’s just like themselves – someone who’s already in tech. So how do you break up this vicious cycle and break-in? The trick is taking advantage of mirror-image biases, aka social engineer decision-makers to see you as one of them already before the interview. Did the hiring managers also break into tech later in their careers? Or she went to the same undergrad or coding boot camp as you? And, like you, did he Teach for America? You get the idea.

Plan your work, work your plan: start with self-discovery and end in mind

A common question we get is “what should I do in tech?” Take this free course from Jeremy if you’re lost. Let me warn you though, not everyone can be a product manager. And there are so many other job functions like product marketing, operations, customer success, and more in tech. Better to break into tech roles that have a tangential relation to your current experience and background. If that happens to be product management, then good for you. Don’t hedge. Make a primary and secondary target role and then go all in. If you need help on this self-discovery and refining your story phase, let us know. In short, you should aim for a realistic beachhead to land. This is how you increase your chance of successfully crossing from “x” industry into tech. Later, (see below) we’ll discuss how to pivot within tech and become Overemployed.

Now let’s get tactically. Look at some backgrounds on LinkedIn with whom you share something common with and reverse engineer to fit your profile with the target profiles of the jobs you want. Our theory is if you can walk, quack, and look like a tech worker, chances are the recruiters and hiring managers will see you as a tech worker as well (or a very good customer success manager, aka you’ve got people’s skills). It works.

Grab the right tools for the break-in job

A complete stranger to LinkedIn? For $49 and some grit, take this LinkedIn mastery email course and change your life. Unfortunately, Overemployed is not closely affiliated with John Steimle & Co. and can only admire them from afar. I did get to take his course for free a couple of years ago, so it doesn’t hurt to reach out and ask for a discount.

Additionally, remote WFH has made it super easy to social network with results, especially when coupled with the right automation like We-Connect. Just proof out your value proposition and messaging first before going full-scale automated. There’s a bit of trial and error in finding your sweet spot. I’d also not use automation on the second-degree goldmines mentioned below with the “I’m hiring” headline. Treat these with a more personalized touch, if you can.

If a lot of what I’ve advocating here sounds similar, it’s because, in addition to my haphazard learnings from breaking into banking, I also read and applied concepts from Predictable Revenue: Turn Your Business Into a Sales Machine with the $100 Million Best Practices of when trying to break into tech as a tech salesperson.

Disclosure: Overemployed is an affiliate for We-Connect. There are a lot of other LinkedIn automation tools but I’ve only used We-Connect and can attest to its simple-to-use interface and effectiveness in getting results.

Profiles with “I’m hiring” – Big red targets for breaking into tech

After understanding your target role in tech and spiffing up your LinkedIn profile, it’s time to cue the human mirror-image bias and social engineer like a CIA field operative. Start by sending one LinkedIn InMail a day, testing out your copy with complete strangers. Note what works and what doesn’t. Continue to drill down your outreach until you get above a reply rate of say 5% (arbitrary number but for reference, a 5% email open rate is considered good). Then try with third-degree connections, second-degree connections, and so on.

Save your second-degree connections with “I’m hiring” or “we’re hiring.” These are goldmines. You want to tackle these once you’ve warmed up and are in tip-top shape because the chances of breaking into tech are highest with these contacts. Why? First, either themselves or their teams have a hiring pain, second, they know of someone who may know you (confidence builder), and finally, you’ve cued the human mirror-image bias and found a list of targets.

Create your own job search CRM (aka excel) to track all your interactions and success rates

Now I haven’t experimented with using a free Hubspot to track my job applications. Perhaps I should next year when I’m on the prowl for the next set of jobs. That said, when I was breaking into tech, the most common “tool” other compatriots used is a Google excel sheet. There are plenty of templates out on the internet on this, but if you can’t find any feel free to email me for a copy. While this method creates its own overhead and can get labor-intensive, it’s still a good idea at least initially to do this. I compare it to personal training to track your workouts. If you don’t track your performance, you won’t know what you’re doing right and more importantly what you’re doing wrong and need course corrections.

Get your tech stuff on point and ready

This one is simple. If you can afford to, get the most reliable cell phone carrier and at least 100 Mbps internet. That’s the basic. Now if you’re a super successful social engineer, and get someone to talk for more than 40 minutes (hats off), then it might make sense to get a paid version of Zoom if needed. For most mortals, a paid Zoom isn’t necessary, though I’d say Zoom is the most preferred with the least technical headaches (like Google Hangout or Meet). Plus, most of everyone is using Zoom so they’re more familiar with its interface. The goal is to aim for the least amount of friction as possible for both sides since you’ve already worked so hard to land these phone calls.

Take The Side Door: Break Into Tech Through Via Other Channels

Here at Overemployed, we’re hustlers at heart. So when the front door is shut tight, we go around to the side or back doors. For those looking to break into tech, that means in addition to Operations Social Engineering, you’re also looking at diversity and inclusion programs and well-vetted career-changer boot camps to help grease the transition.

Are you a mom who enjoys coding? There are MotherCoders (out of all of them my favorite, unfortunately only available in SF or NYC). A military veteran or spouse of a veteran? Here’s Breakline (only learned about this recently, but looks super cool!). Finally, the Grace Hopper Fullstack Academy. If you remotely can understand code, breaking into tech could be for you. For other functions, there are other routes like starting from the bottom up at a start-up and get into tech business roles from graduate schools. My general point here is there are tons of side and back doors to break into tech. Keep your head up, ask for help, and you’ll find a way. If you know of other side doors, please do share in the comments. Let’s lift each other up.

Systems Win Championships 2.0: The Pivot To 2X Once Inside Tech

Now that you’re in tech, whew, ready for the next challenge? How to morph into a polymath that every employer needs. While I think this topic deserves an entire post itself, I’ll briefly touch on why a generalist-with-some-specialty thrives in a specialized world. Try to think of this in the context of 2x Overemployed.

Because tech is changing ever faster, it’s far more important to be a generalist with a few sub-specialties than a super-specialist in one specific tech stack or domain. Not only does this prolong your employability, but it also makes life and work much more fun and interesting. While I’m purposefully being vague here, once in tech I soon realized if I want to keep working into my 50s, I better develop some sub-specialty in a couple of fields and work across a few major tech sub-industries. That’s why I’ve been able to 2x Overemployed without ever running into working for competitors. For the 2x-ers, it’s better to be a smart-ish small fish in a big ocean than a big specialized fish in a small pond.

For example, during the Pandemic and mass unemployment, most of the states’ unemployment IT systems crashed. It was built on a programming language called COBOL. Now if you doubled down on being a specialist in COBOL, then you had endured a very long and slow career death march, until now. The funny thing is during the Pandemic, all of a sudden the demand for COBOL programmers sky-rocketed due to the massive system crash. The lesson here is to specialize with care. Key Takeaway: as a knowledge worker, if you ain’t changing with the times, you’ll get left behind.


  1. Do you know any companies\webpages that hire direct contractors\”normal” job from Eastern Europe? I’m thinking about 100% remote offcourse:)

  2. Anyone have luck finding the “free” course by Jeremy? Only received a syllabus with no following contact and a link to pay for master classes.

  3. I’m loving all the great info/strategies shared here. I do find it interesting though that after being warned MULTIPLE times to “keep my head down” and “don’t talk about 2x employment” every link wants me to enter my personal information. I guess I’ll have to pull out my secret persona (usually reserved for FB marketplace transactions) if I want more information.

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