What makes a successful career? Candid advice from talks with 30 leaders

We met in the front row of our operations management class during our first week of business school at MIT Sloan. Like-minded in our preferred place to sit in class and both management consultants, we became fast friends.

We also shared the same problem: We didn’t know what we wanted to be when we “grew up.” It seemed like most people in business school had it figured out; we were less sure.

With the alumni network at our disposal, we turned to people whose careers we admired and asked them the questions we had:

• What makes a successful career?
• How do I know when it’s the right time to leave one job and move to the next?
• How much planning should I be doing about my career vs. how much should I leave to serendipity?
• What’s the best way for me to articulate my generalist skills? Do I need to specialize to some degree?

Eventually, we started to record the conversations we had. We distilled them down to 20 – 30 minutes of the best content, and that is how our podcast, “How I Got Here,” was born. We launched over a year ago and have done more than 30 inspiring interviews.

Here are some of the things we’ve learned:

Diversify your passion portfolio

We have never expected more from our careers. Jobs purport to give us everything: belonging, purpose, meaning, community, and an identity. Buying into this mindset can lead to unhealthy results: when work does not go well, you will feel unwell.

For me, the key to avoiding this cycle is to diversify the things I am passionate about and dedicate my time to. Kat Cole, former President and COO at Focus Brands, shared in our interview how putting more time and energy towards volunteer work made her happier and ultimately more effective. By diversifying, I lower the stakes for what work needs to do for me — and all my human needs can be fulfilled with a variety of pursuits. — Eric Eliasson

Chase the real air, minimize the fake air

One of our guests, Steve Cook, LGO ’98, executive managing director at LFM Capital,  discussed his work in terms of “real and fake air.”

For him, “real air” was being on the deck of the aircraft carrier watching planes take off during his time in the Navy, or walking around the plant when he was working in manufacturing, both of which gave him energy. “Fake air” was what happened below deck — it consisted of meetings and bureaucracy. Steve knew it was time to reevaluate a role when fake air began to consume him.

Every job I have is likely to include a combination of real and fake air. While fake air cannot be eliminated, I focus on finding ways to structure my time to maximize my real air to fake air ratio so that I remain energized about the work I am doing. — Lara Mitra

Be open to changing definitions of success

Despite all evidence to the contrary, none of our guests believe that they have achieved a successful career yet. There’s always so much more work that they want to do. In fact, many believe that if they did feel like they had “made it,” something would be very, very wrong. They’ve all experienced success, but the feeling is fleeting.

We can’t help but move our own goal posts. Given this, I want to make sure I’m not optimizing my career decisions around some theoretical endpoint of success. Instead, I view success as learning from each of my roles and thereby better honing in on the overlap of what the world needs and what I’m good at. — Eric Eliasson

Remember that planning makes perfect

We bring intention to the work that we do all the time — we plan for how we want to use meeting time, how to execute a project, and how we'll communicate our ideas. But I realized I was slacking when it came to planning my career development.

Here are a few of the tactics our guests have used to take control of their career development:

• Veronica Armstrong, CEO of Isle de Nature, keeps every performance evaluation she gets and revisits them periodically to hold herself accountable to improving her areas of weakness.
• Austin Martin, MBA ’07, vice president of Strategy and Operations at security developer Snyk, blocks off two hours on a Friday of each month to read articles that feed his professional soul and offer inspiration and research on career fulfillment.
• Kat Cole “checks in” with the people she works with every month and asks them, “What’s one thing I could be doing differently to be more effective?”

— Lara Mitra

And yet, don’t underestimate the power of acquaintances and serendipity

We’ve heard time and time again how it was some chance encounter or a friend-of-a-friend that ultimately led to landing the next dream job. On the surface this sounds surprising, but in reality it makes a lot of sense. Your inner circle of close friends and relatives are likely to be more similar to you and therefore have the same access to information as you; on the other hand, it’s acquaintances who are most likely to bring new ideas, ways of thinking, and unfamiliar career opportunities.

Now I ask myself: How do I ensure that I’m getting exposed to people and ideas outside of my usual paths? I’ve personally seen the benefits of a simple commitment to making at least one cold outreach connection every single month.

If that’s too much effort, try this approach from EverQuote chief people officer Elyse Neumeier, MBA ’14: She says “yes” to every recruiter who reaches out and at least takes an initial call with them to learn more about the job they are recruiting for.

Many of these conversations may not go far, but it only takes one to send you down a new exciting path. -— Eric Eliasson

Take action first; confidence will follow

We’ve asked many of our guests something along the lines of, “How did you gain that kind of confidence?” in response to something bold or brave that they did in their careers. Their responses show that even if you don’t feel confident, you can still act in a way that manifests confidence. In time, repeated acts of bravery will build a feeling of confidence.

For example, chief people guru at A Cloud Guru Lorraine Vargas Townsend’s act of bravery was to make her most ambitious goals and desires known to all those around her. Making her goals public not only made her work harder to achieve them, but also enlisted the support of others, boosting her confidence.

To build my confidence, I now strive for moments of bravery to take “confident” actions and, based on the experiences of our guests, trust that the feeling will follow. — Lara Mitra

Choose your company wisely

When deciding between two different jobs, it is common to compare prestige, title, responsibilities, and pay. Our guests didn’t offer these as the most important items to weigh when determining what should come next.

Instead, they emphasized evaluating the people with whom you’ll be working. When taking a new job, they understood that they were not just selecting their title; they were signing up a crew of people to join them on their career journey.

My coworkers are going to become my mentors and confidants; will I like their advice? Do they inspire me? Would I be happy becoming more like them? Will I be happy spending the majority of my waking hours with them? This line of questioning can make the choice between two seemingly similar jobs obvious. — Eric Eliasson

Don’t let a crisis go to waste

MIT Sloan senior lecturer Miro Kazakoff, MBA ’11, gave us this advice in early 2020 in reference to COVID-19. Miro saw the pandemic as an opportunity to revisit the prior “rules” he had set for himself and determine which ones no longer applied. Doing so allowed Miro to completely reimagine how to teach his communications course, making changes that could last well beyond the pandemic.

We’ve heard variations of this advice from other guests ever since. They have been able to turn getting fired, making a huge mistake at work, choosing the wrong job, or enduring a calamity in their personal lives into the “best thing that’s ever happened to them” by reflecting on the experience and being deliberate about what they will do differently moving forward.

Hearing the experiences of our guests has shown me that not only can I learn from my own crises and mistakes, but I can also learn from those of others. Now, in coffee chats, I don’t hesitate to ask: "How did you bounce back from challenge X?" or "How did setback Y influence your approach going forward?" It’s been pleasantly surprising to learn how much people will share if you just ask. — Lara Mitra

Careers are long; take the time to explore

Before we started this project, Lara and I felt perpetually behind. How could we dream of ever being successful in our careers if our peers already had strong convictions about their passions and head starts measured in years?

Happily, our interviews have given us solace. We have heard so many stories of successful people who didn’t follow a clear, linear path.

Paul Sagan, senior advisor and executive in residence at General Catalyst, spent the first 10 years of his life in journalism and media before pivoting into technology startups and ultimately becoming the CEO of Akamai Technologies.

Our first guest in season two, Natalie McCullough, president and chief commercial officer at Guild Education, started her career as a geologist. These are just two of the many winding stories we heard throughout our interviews.

Don’t feel behind. Rather than comparing myself to others who have “figured it out,” I focus on how I get to know myself better each day. Each role is an experiment that helps refine my hypothesis for where I should go. Taking the long way may be the only sure way of getting there. — Eric Eliasson

Ask yourself, “Am I going to be excited to tell my grandkids what I did?”

Chris Bell, CEO at e-commerce company Perch, told us that his definition of what makes a successful career boils down to this question: “When I’m 65, am I going to be excited to tell my grandkids what I did?”

I hope we all craft careers for which we can answer a resounding “yes!” to this question. — Lara Mitra

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Eric Eliasson and Lara Mitra, both MBA ’20, are co-founders of “How I Got Here," a podcast that features successful professionals sharing the twists and turns of their career journeys. Their second season launched in March. To stay up to date, follow their LinkedIn page or sign up for their newsletter on Substack.

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