‘The Long Game’ offers timely look at long-term career planning

So, there is no better time to add Dorie Clark’s Wall Street Journal best-seller, “The Long Game: How to Be a Long-Term Thinker in a Short-Term World,” to our compliance library. In her book, Clark challenges us to ponder what it would look like to “discover our own definition of success, and live life on our own terms?” Yet, how can we be so introspective about our futures and career paths while at the same time feeling “rushed, overwhelmed, and perennially behind”?

I read Clark’s first book, “Reinventing You: Define Your Brand, Imagine Your Future,” while I was incarcerated in 2013, and her work took me on a journey from despair to hope. So, it was a pleasure to take a deeper dive into “The Long Game” as part of a Q&A with the author.

Q: As corporations are in such a time of change, compliance personnel might find themselves in a place much different than where they started with their organizations. Is this a good time to take a pause and think about our professional path forward, and if so, where might someone begin?

A. COVID has prompted almost everyone to reflect on where and how they work. There’s the obvious, like the shift to remote or hybrid work, and of course, we’re in the throes of the so-called ‘Great Resignation,’ in which many people have decided their current company is not right for them.

Separately, and additionally, I’d urge professionals to ask themselves a few strategic questions that are useful to ponder when—in times like these—circumstances have changed and we might want to update our goals or objectives:

• What should I spend my time doing?
• What are the 20 percent of my activities that will yield 80 percent of results?
• What can I stop doing?
• How can I use constraints to my advantage?
• What are my hypotheses about the future—and how do they inform my actions today?

Q. You wrote, “It takes courage to be a long-term thinker, and a willingness to buck the near-term consequences.” What if those consequences might mean a “downward shift” in one’s career path? It’s not easy or instinctive to sacrifice our dignity and pride in exchange for thinking long about our careers.

A. Doing something different from the norm, or from what others are doing, almost inevitably means you’ll hit some roadblocks. That can feel discomfiting for successful professionals who are used to doing things well, and of course none of us like to feel we’re stagnating.

One of the most important things to keep in mind is that our career trajectory is not linear, and we sometimes need to take a step backward (or a perceived step backward) to gain the experience or connections we need to vault forward.

In my own case, I’m a former award-winning newspaper reporter; when I entered the world of consulting, I knew I could expand my profile and reputation if I started writing for free about the topics for which I wanted to be known. I reached out to dozens of publications, and the vast majority either ignored me or turned me down. So, sometimes you do have to swallow your pride. But persevering on that front and ultimately becoming a regular contributor for publications like Harvard Business Review and Fast Company has enabled me to grow my platform significantly, leading to business growth in the end. Part of playing the long game is being resilient.

Q. You address the need to create some “mental space, and a little time, in order to think.” Yet, time is the most precious commodity now, where “our stuffed calendars tend to be a prison of our own making.” Any starting points in how to create that mental space?

A. These days, almost all of us are feeling overwhelmed. Understandably, we tend to look for a magic bullet that can solve our scheduling problems and ease the pressure a little bit.

We think, ‘If only I could take a sabbatical!’ Or we envision some future time when things will have eased up, but of course the problem is they rarely do.

I feel like most of the gains we can make are around the edges, and so the challenge I’d like to issue is to see if we can find ways to create an additional 30 to 60 minutes for ourselves per week. One low-hanging-fruit strategy I recommend is to develop a standard operating procedure, so that when anyone asks you for time on your calendar, you respond first by asking what they want to talk about and how you specifically can help. We tend to assume other people have thought that out, but the truth is they often haven’t, and in the process they can waste a lot of our time. It’s our job to be vigilant and protect against that.

Q. In thinking long, compliance leaders might need to reach out externally to colleagues for brainstorming. This has become less organic in a remote environment. How can people reach out for support and counsel where both parties can “enjoy the experience and let it unfold organically”?

A. It often feels awkward to be in touch with someone you haven’t connected with in a long time. You might hesitate to reach out because you wonder if you’ll be bothering them, or if they’ll think it’s strange or that you want something from them.

The truth is most people are happy to hear from you. It’s fine to tap an old colleague or friend for their advice or perspective. The thing you don’t want to do is to suddenly get back in touch with someone and ask for a favor that involves political capital. That’s where people can begin to feel used.

In ‘The Long Game,’ I discussed the importance of cultivating long-term relationships as compared to short-term networking, which is a situation where you need something fast and try to extract it. We should try to avoid this situation whenever humanly possible, because understandably it makes people feel very uncomfortable. While you might be able to get something in the short term, they’re going to pull away as soon as it’s feasible.

Q. What would you say to someone who has been trying to do all the above to no avail, other than feeling frustrated and even more overwhelmed. Can you share a few words on how to “rethink failure”?

A. We really need to reframe what failure means. Often, we have an idea in our heads that if something doesn’t work out exactly how we’ve planned, it will lead to dire consequences. But that’s only true when you’ve put way too much at stake.

A far better plan is to identify the smallest bet possible that you can place so you can test assumptions and see whether a particular idea or course of action is gaining traction—and whether you enjoy it. If you’re getting good feedback, then you can devote more time, energy, and resources to it. And if no one seems interested, you can abandon it before it takes up much time.

Before a certain level, it’s almost ridiculous to call something a failure. If you put down a $1 bet and it doesn’t work out, is that a failure? I’d argue not; it’s just too small to be a big deal. If we can be strategic about placing small bets, then we can eliminate the fears and existential threats around making dramatic choices and simply hoping and wishing they’ll work out.

Thank you, Dorie, for sharing your perspective with Compliance Week. Readers can download the free “Long Game” strategic thinking self-assessment here.