Thinking of Changing Careers?

Don't Quit Before Reading This First

Let’s just say, my career path is a little well, off the path.

I’ve gone in and out of a bunch of professions, and even crossed domains while I was at it. Now, my career is entering its third decade so father time has definitely been a factor, but I will put up these experiences and let you be the judge:

Job Functions:

- Inside Sales
- Technical Engineer / Coder / Architect
- Entrepreneur / Startup Founder
- Investor
- Advisor

Domains:

- Recruiting
- Investment Management / Hedge Funds
- Biotech / Health and Life Sciences
- Philosophy / Wellness

I was able to work in the above roles and domains at some of the most competitive companies, including McKinsey, Bridgewater Associates, Wellington Management, Temasek, GIC, and so on. What would possess these companies to hire me, in senior positions, across job functions and domains? Did I hoodwink them in my interviews and faked it ‘till I made it?

The answer is that I have found techniques to change careers, and not only switch but to excel at them to gain entry into highly competitive companies.

But first, let me make a couple of confessions:

1. I am not super smart. I did not graduate from an Ivy League university. At the same time, I’m not an idiot and possess some common sense

2. I am not gifted in anything. No matter what area, I am nowhere near the top of the heap - there are a whole bunch of people way ahead of me in capabilities and expertise

In other words, I’m not special - I am just like you (sorry for assuming that you aren’t a genius). I’m just a regular fella, which is why what I’m about to share with you is something I hope you can appreciate, and ultimately benefit from.

From Sales to Tech

Here’s the truth - I was never trained as a sales person, and I have never taken a computer course in my life. So how did I do it?

Well, for sales, I started as an intern at a executive recruiting company making cold calls doing inside sales. So basically, it was the first job I had and by starting at the bottom, I had the opportunity to learn how to do the job. This shouldn’t come as a shock to you, but I’m guessing that you don’t want to start from the bottom of the barrel, especially since you already have a career going on, right?

Then how did I switch from an inside sales, cold caller in a recruiting company to become a Sr. Web Engineer and Assistant Vice President at Wellington Management Company, an investment firm with over $1T+ in assets?

Here’s what I did: I understood that there was this game changing thing called the Internet (this was back in 1996) that was rapidly growing, and that it was so new that there was no specialist who had 10 years of experience doing it.

That meant, the playing field was level, and that is the key bridge I used to traverse into the tech space.

Of course, I had to learn and become as proficient as I could with Internet technologies from the TCP/IP stack to Javascript but these things were evolving so quickly that any legacy knowledge was basically useless - and I used that to my advantage. There was no “pedigree” in the field, at least, not yet.

I walked into the interview with a CD-ROM I burned (USB didn’t exist yet, and yes we burned CD-Rs back then) containing my digital portfolio. That’s all that mattered - my age, resume, past history, etc had no bearing. Wellington Management needed a capable person to help usher Internet technologies into the company, and that CD-ROM provided the proof. There was no other alternative.

The first lesson here is: find a game changing innovation that is progressing so rapidly that it has levelled the playing field. Once you find it, become an expert at it (the Internet has disrupted learning) - this requires a huge amount of effort and will, so of course, it helps if you genuinely have an interest in the field.

Innovation is always happening: back then it was the Internet, today it could be AI. Whatever it is, it is a potential bridge to another career altogether.

From Tech to Investor

I built a career on tech that spanned a whole decade and traversed investment management, consulting, and eventually landed me a job at Bridgewater Associates where I was intrigued by Ray Dalio’s Principles. That’s where I quit that career, moved to Silicon Valley and became a startup co-founder and entrepreneur as the CTO of Been, Inc.

Now, anybody can quit one’s job at any time and become a startup founder - that’s not the point. Rather, it’s knowing when to do it, under what risk parameters, financial preparedness, and most importantly, personal motivation that has propelled oneself to take the leap.

This topic deserves its own separate post in the future, so fast forwarding to the outcome of our startup getting kicked out of the Apple Store and me getting banned by Apple (you can read more about that over here), I was faced with a dilemma: what was I going to do next?

I sure as hell wasn’t going back to Corporate America - what more would I learn by doing that? And boy, was I fatigued - there was no way I could embark on another startup. I needed a break… or so I thought.

The realization that I was asking the wrong question materialized one day: it wasn’t WHAT I was going to do, but WHERE I was going to do what. All of a sudden, the clouds parted and the entire world became fair game. I thought that the startup scene in Southeast Asia was primed for growth (this was back in 2016) and decided there was no better place to take my Silicon Valley experience to. And so I packed up and moved to Singapore with my wife.

Throughout my stay in Singapore, I was an innovation and entrepreneurial lead working at senior roles at both of Singapore’s sovereign wealth linked entities: GIC and Temasek. I created accelerators, investment programs, and advised them on various spinouts they were creating. Over time, my performance and expertise translated into trust and credibility when it came to investment decision making for startups, and that’s how I eventually became an early-stage investor, completing my transition from tech to investing.

The second lesson here is: don’t limit yourself geographically to wherever you are. Think big - as in, the world. Look for places where your skills and experience are desperately needed, and move there. Doing so will open doors that previously were shut in your city and even country. And that is another bridge you can get on towards a new career in a completely different field.

These are just two examples I have used in my past that have led me to where I am today at FoFty. If they make sense to you, then check out the video I made on this topic where I talk about other techniques along with the experiential aspect of switching careers over here:

Changing careers may seem daunting, especially when you are in mid-career, amassed responsibilities, and don’t have much flexibility in terms of taking steps backwards in order to move forward.

The methods I describe above and in the video provide lateral pathways that not only can get you to a new career, but do so at some of the most competitive organizations in the world. I’m living proof of it.