How To Reimagine the Second Half of Your Career

07 October 2020 Brijesh Mongia

Aug20 18 88830738

When I graduated from college in 1995, the last thing I imagined being was a manager in UX design, which was a relatively young field where we ensured the customers and users of our websites, apps, and software could easily use and enjoy these services. My dream was to be a professional musician — a rock star — and I pursued that goal for several years.

I landed a six-month internship at Soundtrack Studios in New York City, and I quickly found out that interns basically did whatever everyone else didn’t want to do. I was working 50 hours a week and getting paid $150 a week for my time. As I learned more about the music production business, I found out that the career path was brutal, job opportunities were scarce, and the pay was minuscule. Assistant engineers — who had been in the business for years — were making only $6 an hour at the time. That felt unsustainable to me. So, I decided to leave my professional music dream behind and find a new career path.

I got a job with a company called iXL doing front-end development and graphic design. Front-end development in 1999, at the height of the dot-com craze, was basically being able to spell “HTML.” As that job evolved, I started reading some very transformational books. One book, in particular, Information Architecture for the World Wide Web by Louis Rosenfeld and Peter Morville, absolutely changed my life. I’m grateful to have met and gotten to know both of the book’s authors over the years. This book put me on track to become a UX designer and an interaction designer, and my career began to move forward in this new direction.

I bounced around several jobs during the dotcom bubble — they were turbulent times, but I was very lucky. I came from a middle-class home in the New Jersey suburbs, had supportive parents and a good education. I always managed to land the next gig. I worked at AOL for a few years, and I learned a lot there about being a designer. I progressed to building a design team with a company on the West Coast called Webtrends, which at the time was the leader of web analytics providers. And then I found my way to New York City where I landed a job leading and building a design team at TheLadders, an online executive job search firm.

But as I faced my 35th birthday, I found myself panicking. I was struggling to envision what the second half of my career would look like when it came to seniority, salary, fulfillment, you name it. Where do I go from here? After all, the farther up the ladder you go, the fewer positions there are — it’s just the nature of the corporate beast. There are very few C-level, chief design officer jobs.

This got me thinking about how we ensure that our efforts, career paths, and viability as valuable members of organizations, communities, and disciplines continue throughout our careers. The answer I found was relatively simple. The work to get there, less so. It’s a concept I call forever employable (also the name of my new book) and it is the continuous sharing and re-purposing of your experience, passion, and expertise to create a platform of thought leadership around yourself. By becoming a recognized expert in your chosen domain or discipline you reverse the flow of job leads and opportunities. Instead of you having to chase them down, they come to you. 

Becoming forever employable doesn’t mean quitting your job necessarily. It is equally applicable for those of you intent on staying employed in-house for the long-term as it is for those with the desire to consult or become self-employed.

There are five core concepts I see as crucial to keep in mind as you think about the second half of your career and building this platform:


I never thought of myself as an entrepreneur. You probably don’t think of yourself that way either. But eventually I had to make a transition that required me to adopt an entrepreneurial mindset and proactively put myself and my ideas out in the open in an effort to attract opportunities, land them, and turn them into successful ventures. This is your life, your business, your employment. And so, you’ve got to think about this challenge like an entrepreneur. Who is my target audience? What problems can I help them solve? What’s the most effective way for me to provide my service to them? These questions start you down the path of building a “startup” centered around yourself.


Sharing your expertise can be daunting. Hasn’t everything already been said about management, marketing, sales, digital transformation? It can feel like it but there’s one story that hasn’t been told yet: yours. Your unique life experiences, diverse paths to your current position and obstacles overcome are the core of your newfound expertise platform. No one else has that. Remember to tap into the deep vein of skills and expertise that is unique to you. When you’re standing at a crossroads in your life, know that you bring something unique to the table — something that no one else has. Embrace it, own it, be it. Your experience has value, your knowledge has value, and you have something valuable to add to the conversation. No one has your story. Be confident in what you know and build on that knowledge as you take on new projects.

Continuous learning

Everything is changing all the time. The only way to keep up — or even better, stay ahead — is to keep learning. You learn continuously by reading blog posts and books, and listening to podcasts and audiobooks, created by people who can help illuminate your path forward. You do this by talking with people who can explain what they did to achieve the success they wanted in their lives. You do this by building communities of expertise and practice around yourself. You do this by constantly experimenting and trying new things. Sometimes your experiments will succeed, and sometimes they won’t. But as long as you learn something from every experiment, you haven’t truly failed. Stay curious. Keep your mind open to the possibilities laid out before you. Experiment constantly, learn from your results, and try again. Like my old ski instructor used to say, “If you’re not falling, you’re not learning.”

Continuous improvement

If you’re learning continuously, and you’re applying the outcomes of your experiments to your platform, then you’re always going to improve and get better at whatever it is that you have chosen to do to become forever employable. In his popular TED Talk, Astro Teller, captain of Moonshots at X (Google’s innovation laboratory), explains that you should be enthusiastically skeptical of everything that you’re doing. In other words, you should always want to figure out a better way to do something. “Enthusiastic skepticism is not the enemy of boundless optimism,” he says. In fact, it’s the perfect partner. No matter how good you believe you are at your chosen profession, being enthusiastically skeptical means you’re always searching for a better way to do your job. In fact, you’re excited to find it. What can you learn from others in your field who have been successful? What about leaders in other fields? What did they do to build their platforms and what can you apply to yours?


Ultimately, becoming forever employable is all about reinventing yourself. I was a designer, and then I was a design manager, and I was going be a super-duper design manager — or at least that’s where I was headed. But, because of the expertise, I was sharing, other opportunities walked into my life. With the help and support of my family, I was ready to seize them. Since then, I’ve reinvented myself on an ongoing basis. Nothing stands still, and the pace of change today is faster than ever. Almost a decade ago, Amazon was updating its codebase every 11.6 seconds — they were essentially reinventing the way that they serve their customers five times a minute. By 2015, Amazon got faster — way faster — pushing code to production every second. Imagine what that figure is today. In 2018, Google revealed that it runs over 500 million tests a day, equating to more than 4 million relaunches of existing and new systems each and every day. That’s the modern pace of change. If you want to stay forever employable, then you’ve got to be ready to reinvent yourself with the times. And that is coming in shorter and shorter cycles.

Re-orgs happen regularly. So do layoffs. Covid-19 has laid waste to entire industries. Technological disruptions automate us out of jobs annually. This doesn’t mean we’re done being useful, successful and viable in the job marketplace. However, being forever employable means you’ve got to be intentional about where you’re going, and you’ve got to be prepared to act — immediately and without hesitation — when the right opportunity presents itself. With a foundation in your expertise, a thorough and current understanding of your domain and an ever-growing network to lean on you can guarantee the next job will find you.

Source: Jeff Gothelf