Ten Pathfinding Principles for Risk-Taking Career Decisions

“A ship is safe in harbour, but that’s not what ships are for.”

On July 20, 1850, a young man named John Graves Shedd was born on a New Hampshire farm. By age 16, he had begun work as a clerk in a grocery store in Vermont. A year later, he found work at a general store, and then at a dry goods store.

On the surface, we might consider that John Shedd’s career trajectory was set. He would work in small town America as a clerk and, if lucky, someday he might even own his own general store.

Instead, by age 56, he was the President of the Marshall Field company based in Chicago, which became under his leadership the largest wholesale and dry goods company in the world. According to the 1921 Cyclopedia of American Biography, the Marshall Field company had over 20,000 employees, the store’s floor space covered 45 acres, and the store had over thirty miles of carpet.

Shedd is also the author of the quote that begins this article. It’s found in a little book of his wisdom called Salt From My Attic.

At age 22, Shedd left his small town home to “go West” to Chicago, where he wanted to work for the best store in the city. After research, he discovered that store was the Marshall Field company. Shedd became a very small fish in a very large pond – beginning as a stockkeeper and salesman.

He left safe harbor and ventured into the great and often frightening ocean, dramatically changing his career trajectory.

A little over a year ago, I did something a little less adventurous in my own career. I moved from a 20-year career as a mergers and acquisitions attorney focusing on international transactions to serving as an executive vice president and general counsel in a regional bank. It was a somewhat significant career shift for an attorney at a law firm. I had spent my career navigating complex closings in different industries — manufacturing and distribution, energy, infrastructure, software, and IT —  traveling the world meeting clients, and gaining an understanding of the culture and legal complexities of countries in Europe, Asia, and South America. There was a natural career path for me in the world of law firms, and I felt like I was at the top of my game. 

In my new career at the bank, I’d still be practicing law, but in a very different industry, one with different rules, a different career track, different peers, different challenges, and a different boss.  I’d be moving from a place where I was free to pursue the clients and opportunities of my choosing (though with tremendous support and very talented and helpful peers) to one that was far more structured and boundaried. Most interestingly, I’d be starting over afresh — beginning “at the beginning” in a new place, with a steep learning curve. 

Over the past year, a number of people have approached me for advice about pursuing a career change. From those many conversations, it’s clear that the question of how we know when to make a significant career leap is a complex and very personal question. 

What causes people with secure jobs to take a risk and change their career trajectories? Perhaps more importantly, how do we define success for ourselves and go about pursuing it?

  Below are some of the principles I learned during my own time of career decisions. 

Recognize that there is no one right answer, and no formula for taking career risks.

Sometimes we look at another person’s career leap and gain strength from their choice. “If he can do it, so can I!” It’s helpful to gain courage from other people’s examples. But our advice to others on career choices should have a large dose of humility. My career decisions are not the “right” career decisions for others. None of us has the answer for any other particular person.  We are all motivated by different things. We all have different passions. Our contexts are different — our families, peers, workplaces, and geographies where we work. We also pursue different “balances” of work, spouse, children, extended family, exercise, hobbies, leisure, and more – and that balance often changes over time in different seasons of life.

We can all offer a listening ear, analysis, contacts, and perspectives — but nobody can give The Answer except you for your own career.

Discover what drives you.

Recently I spoke with an attorney who has been with a large law firm for about 10 years. (I have changed the names of examples in this article to preserve privacy.) Bill recently made partner and is considered a rising star. However, he has three children and during 2020 when working from home, he enjoyed spending more time with them. Bill works on complex litigation cases across the country.  His work is for large corporations and very profitable, but Bill is not feeling engaged in his work. Bill has come to a difficult conclusion — he doesn’t see himself continuing the lifestyle of a law firm partner. 

There’s no doubt in my mind that Bill would become a law firm leader if he wanted to pursue that goal. Many attorneys are driven by that career goal. But Bill isn’t. Bill is no longer fulfilled by his work. His recognition of that is courageous, and he called me to help him envision a path to find an in-house position locally – at a company where he can develop relationships and where he can feel that his contribution makes a difference.  

I also chose an in-house position — but my decision was based on different drives than Bill’s. My primary drives are growing and learning, leadership and team building, and mastering another type of work. If you can identify what drives you, you will have a much better shot at finding the opportunity that satisfies those needs.

Recognize that different seasons of life require different strategies and different timelines.

Stephanie has young children and works at a mid-level job at a global company. Her job is not challenging, and she’s not had managers that inspire her or help her with her professional development.  She no longer sees her company as the place she wants to be. Stephanie thinks that she might want a big change – possibly changing industries – and most likely wants to work part time.     

Stephanie is in a “season of life” with young children that is rewarding, but also sometimes exhausting. Taking a step back right now and re-evaluating her career path may be a healthy option. If Stephanie takes this time to evaluate her options, she may gear back up on a more fulfilling path. 

If Stephanie were very passionate about her job, I would give her the opposite advice.  I remember the years when my children were small as being the most challenging of my life (they are mostly a blur). However, I loved my work and I “leaned in” during that time to come out the other side as a partner with the luxury of being able to control my own schedule and delegate work to other team members. But that’s not for everyone and you have to have passion for what you do to push through a season like that.

Choosing to take a risk with your career — or choosing to sit tight for a time — has so much to do with your context. Are you working through a health issue or caring for an aging relative? That may not be the time to take on a new work challenge. Conversely, if you have “made it” in your career and are wondering what’s next — perhaps that’s the time to think bigger or look farther afield.

Make the most of where you are.

Steven approached me for some career perspective recently. He is general counsel for a small company.  He is a relatively young, about 6 years out of law school.  Steven was hired as the company’s first lawyer. The company is growing at a rapid rate, and Steven has been gaining responsibility and getting fantastic experience. Over his 3 years at the company, his role has been expanded to oversee legal, compliance, and risk. Steven loves the company, enjoys his colleagues, and is completely satisfied with his job except for one thing.  He feels that the company does not pay him enough for his role — and he’s probably right.

It’s not okay to feel undervalued for your work and that can’t last long term. However, it’s rare to be at a company where the culture, role, and responsibilities are rewarding. Steven has been given significant responsibility at his current company, but he may not have been there long enough to establish a track record to qualify for a similar role at another company. If Steven can get his salary to a place where it’s tolerable for him, it may be worth Steven’s time to spend a few more years at this job to gain experience needed for his next role. If he sticks it out, Steven will continue to gain valuable experience that could launch him into a similar or even greater role at a bigger company.

Know when you’re finished where you are.

Sometimes you know when you’re done at a company, firm, or job. You’ve mastered everything you can. You’ve achieved. You’ve received promotions. You’ve made the money that you wanted. And there’s seemingly nothing left to conquer where you are. You sense you need a new challenge. But that means leaving where you are — the comfort, the sense of mastery, the success, the acknowledgement from your peers — and going somewhere else. 

It’s easier to settle and get complacent. Moving away from that comfort, in a place where you’re good at your job, and into something new means taking a risk and that takes courage. 

Some who find themselves in that situation make the decision to pursue outside interests, and get their stimulation in other arenas. 

Others, though, love to work, and need to work where they are challenged — where there is something more to master.

I’m reminded of a friend of mine who came to that conclusion at one large company. He felt that there was nothing more to conquer there — and he also felt as if he was stagnating and growing bored. He needed to have the thrill of something to learn, some new quest to pursue.

“I’m done here,” he told me. He needed to find a new challenge.

And he did. 

Build your network now.

It takes significant connections for someone who is mid-career or later to shift career direction. I think of one friend who was on a career trajectory (towards bigger promotions, more money, prestige, and travel, along with national responsibilities) and realized he didn’t want the additional hours and the less satisfying work. The longer he stayed on that path, the more he would be stuck.

However, he had not yet built his network to a place where he could easily make a move. He began reaching out after he decided to make a move — but if he’d built his network years earlier, that transition would be swifter and allow more options.

Sometimes in that instance it’s wise to step back, hold in your position for a year or so, and focus on the networking that will allow an ideal job search to find a company that is a cultural match.

Have confidence in yourself.

Navigating significant career shifts requires tremendous confidence in your skill set, your experience, your ability to learn and flexibly respond to new challenges, and your willingness to start over and to begin again. It also requires confidence in your “core” — which is different for everybody.

As I was considering my own career shift, I evaluated what I really needed in my life, and it turned out that what I needed was my husband, my children, and the care of dear friends who are non-judgmental. I am extremely fortunate to have such a base in my life. With strong supportive relationships, I felt that I could take on the possibility of failure and pursue the adventures involved in a significant career change. I also knew that if needed, I have experience and skills that translate into other opportunities.

Learn to relish the adventure of being the new person, starting over, and the clean slate.

Megan is extremely driven and was very successful at a national accounting firm in California where she was a partner. She is happy spending lots of time at work, where she was a star. Her husband stays home with their two children. 

However, Megan and her family decided they needed to make the move from California to South Carolina to be near family.  To do so, Megan had to make the difficult decision to start over and rebuild at a new firm in South Carolina — an incredibly hard and risky thing to do at her stage of career. She has plunged into this challenging career adventure, at a new firm, where she is making a splash, but she did have to, in many ways, start over. She has had to build new firm relationships, a new client base, learn a next context and culture, and “prove herself” all over again to new peers and clients. 

I believe that a very driven talented person can rebuilt and succeed, but there’s always risk to starting over. Anyone can fail in certain environments (some environments are toxic). I love Megan’s story because she made a career move while already successful and gave her all to the challenge. 

Our career choices are more about how we are going to live — and age — than anything else. 

The great English novelist George Eliot said “It is never too late to be who you might have been.” My instinct is that career changes feel easier the younger we are in our careers. For many, once we have reached a certain level of success and comfort, complacency can set in. I have friends — executives at large companies and partners at law firms and accounting firms — who have reached career pinnacles but who are no longer energized by their work. Those friends are not unhappy “enough,” however, to make a change. In some cases, their choices are limited because they have achieved certain lifestyles and a change may result in less compensation. 

Sometimes the answer may be to travel, to enjoy other activities, to get stimulation elsewhere than work.  I tend to think, however, that work takes up such a huge amount of our time that being motivated and having challenges at work is important – and sometimes it means that you have to change jobs or roles to achieve those things.

It may sound trite, but it is a truism that life is short. Knowing this ought to make us more assertive about how we spend our limited time. Life is too short to waste time on things that do not give you joy and energy. Life is too short not to develop close and life-affirming relationships. And life is too short to not take careful risks to pursue a career — and life — that is richer and fuller and more meaningful. 

Push until you die. 

With the above in mind, my philosophy on life and career choices is to keep pushing. Keep learning. Keep growing and pursuing. 

This does not always mean that we focus on work. It may mean that we choose a career that allows us to focus more on outside interests or family or other relationships. I think of a friend who is pursuing a master gardener designation. She’s not “coasting” or unmotivated or settling — she’s pushing on a hobby that she deeply enjoys and finds meaningful. Another friend is studying to get his sea captain license.  Another is building his dream house getaway in the mountains.

No matter the age, this philosophy of continued improvement, learning, stretching, growing, and pursuing challenge is a highly motivating one for me.

There’s one more over-arching principle I’ve learned about career challenges and shifts — but it’s more to do with life than career. 

In all of our decisions, adventures, challenges, and anxieties about work, relationships, family, and leisure, Sir Edmund Hillary, the great mountaineer and explorer, sums up the real struggle best:

“It’s not the mountain we conquer, but ourselves.”

Written by Melinda Davis Lux.