Career Relaunch
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Career Relaunch

When You Face a Fork in the Road

How do you know if a career choice is the right one for you… or not?

By Stephen Dupont

At some point in your career, you will face a big opportunity or challenge that — based on the decision you make — could significantly alter the path of your life.

One of those fork-in-the-road moments came for me as a young account executive working for a Minneapolis-based advertising and public relations firm.

I received a phone call from a devilishly smart headhunter on a frigid day (-10 degrees Fahrenheit) in January to consider moving from Minneapolis to Los Angeles to work on the Tourism of Malaysia account.

Needless to say, it was a very tempting opportunity…as you might imagine. Plus, it was such a career boost — to feel recruited by a large L.A. firm to work on a major account.

For most people, it’s only a matter of when — not if — such moment present themselves.

For example:

— Choosing between a full-time job or pursuing an MBA;

— Wondering if you should marry a person you love who wants to move to the other side of the country to complete his Ph.D., which means giving up your fast-paced job for a highly regarded Fortune 100 corporation;

— Being offered an opportunity to jump in at the ground floor in starting a new company;

— Choosing to not pursue a traditional white-collar job for an opportunity to manage a camp that teaches teens wilderness skills.

These and many other choices can be gut-wrenchingly complex.

So, how do you know if an opportunity, an invitation, a piece of advice or a specific challenge is good for your personal growth and career development?

Similarly, how can you attract more opportunities that excite you — to give you more options to choose from?

As a mentor, I’ve helped friends, colleagues and peers work through some of these critical moments.

What I’ve learned is that if we are clear about what we want, who we want to be and the direction that we want our careers to take, then those fork-in-the-road decisions will be easier to make.

We will attract more desirable opportunities and the inevitable bumps in the road will become less stressful.

If you’ve ever planned a long vacation trip, then you have a sense of what I mean. A very clear vision, plus persistence, equals a more rewarding trip when the hiccups occur.

Or, here’s another example: When I was younger and decided I really wanted to buy and own my own home, I did everything to prepare myself for that moment. I paid off all my debt (including my car loan and student loans), and I built up my savings for my downpayment. When I determined this, everything became very clear as to what I needed to do to achieve that goal — taking lunches to work every day, cut all spending to the minimum (no coffees, no more music purchases, no concerts, no trips), etc.

“The secret to making good choices is to be conscious of the larger picture that you want in your life,” says Keith Ellis, author of the best-selling book “The Magic Lamp: Goal Setting for People Who Hate Setting Goals.”

“This includes who you want to be, your career aspirations, what kind of a legacy you want to leave, your financial objectives, your health goals, and what kinds of relationships you want to have with your family, friends and colleagues.”

Résumés, work samples and a robust LinkedIn profile are important components in advancing your career, but the greatest tool you have is the high-level thinking about your purpose and path that you need to give yourself time to do throughout your career.

To make sense of those inevitable opportunities and challenges, here are three tools you need to acquire in advance of the big opportunity:

— a manifesto statement,

— a short list of filters or screens, and

— a mentor team.

When combined, these create a system that will make short work of big choices.

Here’s how to acquire those tools:

Step 1: Write your manifesto

Why do I do what I do?

What am I really good at?

What need am I serving?

Who do I want to work with?

How will I make the world a better place?

What am I truly passionate about?

What’s the demand for what I want to do?

Answering these basic questions will provide you with the compass that you need to set some career goals.

Put your responses to these questions in writing. The shorter, the better — but make sure that it’s less than 750 words. Keep your manifesto close to you.

Reflect on it frequently. And keep refining it. I’ve boiled my statement down to this: “CCC” (work with Cool people, doing Cool things, to achieve Cool good).

Step 2: Define your filters

Within the context of your purpose statement, create and prioritize a list of value statements by which to screen an opportunity.

When an incredible new job opportunity arises, these filters will help you determine if it’s a good fit for you. These screens may also help you see if you’re in the right place for long-term career happiness.

For starters, consider these filters:

  • Family and friends (How critical is it to be near family and friends?)
  • Passions (Does your career choice intersect with a personal passion for things like chocolate, beer, downhill skiing, cycling, art, barbecue or baseball?)
  • Place (How important is your location? Do you want to live in a big city or a small town? A place that inspires you like the mountains or ocean?
  • Travel (How much are you willing to travel for a job?)
  • Politics (How important is an organization’s politics? Would you join an organization if the CEO has personally contributed to a cause that you disagree with?)
  • The organization (How important is it to work with or for a company that others perceive to be world-class, such as Apple, Google or Burberry?
  • Your partner’s dreams (How does each opportunity help or hinder your loved one’s dreams?)

I used filters like these to determine that that incredible opportunity to work on the Tourism for Malaysia account was not a good fit for me. While I love Southern California, I love hockey and winters even more — as well as being close to good friends and family (I have three brothers).

Step 3: Form a mentor team

To help you think through some of these important questions, invite a handful of people to serve as your mentors. These should be people you trust who will listen to you, challenge you and inspire you.

Multiple perspectives will help you recognize the positive and negative patterns in your life, and reframe your mindset to better understand your potential as well as alternative possibilities that you haven’t thought about yet.

When you have these three tools, you take the gut out of the decision-making process.

Instead of relying on luck, you will take steps with intention.

The goals that you set will be more realistic, relevant and authentic to you. You will be more apt to act on an opportunity rather than let it dance around you.

The next big leap from here is to start proceeding with your manifesto statement. Take the luck out of those opportunities that pop up from time to time, and start making opportunities that allow your dreams and wishes to happen more frequently.

If your manifesto statement and conversations with your mentor team point to a future with a cool agency in Los Angeles, then take the time each day to pursue that dream by researching agencies, checking your LinkedIn contacts and seeking informational interviews.

“Luck happens all the time to all of us,” Ellis adds. “But it only matters — it’s only lucky — if we know what we want, and we are open to the changes necessary to get it, such as relocating, learning new skills, earning a little less for a while to start over in a new field, etc. If you haven’t bothered to figure out what you want from life, then how will you know when you get it?

“Many of us never understand that the hardest work there is,” Ellis continues, “the work many of us resist, is figuring out what we want from life, and being willing to change in order to get it.”

Did you find this article helpful? For more articles on careers, marketing, curiosity and technology, visit

Stephen Dupont, APR, is VP of Public Relations and Branded Content for Pocket Hercules (, a brand marketing firm based in Minneapolis. Contact Stephen Dupont at or visit his LinkedIn profile at



Stories about how to make a brave career change. Curated by Joseph Liu, host of the Career Relaunch podcast.

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Stephen Dupont

Minneapolis public relations/marketing professional exploring creativity, idea generation, careers and change. Subscribe to my blog at