Career Risks: How Do You Make the Leap?

For this article by Jo Ilfeld, Executive Leadership Coach on career risks the image shows a woman leaping across some rocks.

Last month I made the leap and got a new puppy. Other than the obvious cuteness factor, why I am sharing this?

Well, recently I’ve been speaking with several clients who are contemplating risky moves in their careers and asking themselves is now the right time. Will I regret doing this down the road? Am even capable of this?

This brings me back to my new puppy.

While you might not connect taking career risks with getting a new puppy, there are relevant parallels that are worth considering.

So for a bit of fun, I thought I would walk through the process of contemplating a big career risk and how it can mirror other risks you may take in your life – or specifically one I’ve taken in mine.

Dr Jo’s Questions To Ponder Before Jumping In (or Off)

1. What’s your Why? What do you want to change?

Initially, getting a puppy seemed impulsive, and why mess up a life that’s working on a whim? However, the more I dug in, the more I realized the shifting dynamics in my household made NOW a much better time to get a puppy than waiting several months or longer. For example, I wanted the puppy to know my son well before he left for college. And right now, my mom and her pup are staying with us for the winter, which makes her pup a great playmate for the new puppy!

Often when my clients are contemplating a big career shift, it’s not the first time they’ve thought about it. Big changes tend to circle around in your brain for a while before you act on them. They might show up in the form of an email that’s initially intriguing, a question from a friend that sticks with you, or even a fantasy that pops up during a particularly hard meeting (“I could just walk away from all of this and be done. . . “)

I had one client who worked on her resume about 5 years ago, then stayed. A couple of years later she did a few informational interviews and checked out a couple of job listings, then stayed. When a major shift happened at her organization, she finally had her Why and determined she would leave within the year. All that initial legwork had made her launch-ready so that when the right moment appeared – she took the risk and jumped.

2. Do you have the energy to mobilize for change? 

Let’s be honest – there are high- and low-energy times in our lives. Some of that depends on what’s going on in the background of our personal lives. If you have young kids, aging parents that need help, or a spouse that’s in full-bore career mode, it might be a time to work on accepting things as imperfectly as they are. When you’re feeling overburdened and dissatisfied with the current state of your world, it’s tempting to consider a bigger shake-up to change it up. While sometimes you’re not given a choice, when you are, it makes sense to determine how many “hard things” you want to be facing at once in your life.

Clues that now is the right time? It’s often when you think about something new and instead of thinking about how exhausting it will be, you find yourself more focused on the positives this change would bring.

Whenever I previously contemplated getting another dog, I felt overwhelmed and resistant. Even a year ago when I had the opportunity to get a one-year-old dog of the breed I love, I only pictured the work. This time, I found myself thinking ahead to all the joy a puppy would bring and the additional love and cuddles in our household.

3. Watch for serendipity. . .  

Sometimes when I have clients who are no longer feeling the love, there might be a re-org that happens internally and suddenly gives them the opportunity to opt out. Another client of mine opened up to having a few exploratory conversations and a new opportunity was offered to her within the week. So look for these signs around you. . .It might be in the form of a friend who you haven’t spoken to in a while who has some great ideas, it might be a chance conversation waiting in line. . .

Don’t get me wrong, there isn’t always a dramatic moment of fate. There is, however, a concept in psychology called the Baader-Meinhof phenomenon, also known as the frequency illusion, where once you’re shopping for a new green minivan, you suddenly notice every green minivan on the road.

So too, when you’re more open to possibilities, you start noticing connections and opportunities that you might have been blind to beforehand.

4. Consult your beloved Board of Directors

Your board of directors is your posse of people you turn to for career and life advice. It might include a best friend or two, a spouse, a mentor from a previous company, your coach (if you’re lucky enough to have one!), and even a savvy family member like a parent, sibling, or cousin who knows you well. First, lay out for them what you’ve been thinking, bring all your Whys, and then ask your board to poke holes in your reasoning. These are the people who will tell you if you’re crazy or if it’s the most brilliant idea you’ve ever had!

When I first considered getting a puppy, I made my mom sit down to tea with me and listen to all my best reasons for why now was the perfect time. Similarly, I ran it by my son the following day on a car errand. Each person gave at least one new thing to consider as well as good advice for if I did choose to go through with it.

5. Last but not least, go inside!

We’re so trained to go instead our heads and reason things out but with big changes, I’ve found the biggest key is to go inside your heart and body and check that they are aligned and ready for this change. Often your head will tell you it’s a good choice, but you’ll find you have a heavy heart or a bit of a stomachache whenever you think too long about it. Don’t just push past these warning signs. It might just mean you need to do more planning, but it might also be an indicator that now is not your moment.

I’ve had clients who had great offers, ones they felt they should be excited about but just weren’t. Listening to your internal “gut sense” is key to having truly aligned decisions.  Just because you are aligned doesn’t mean it’s guaranteed to be a success, but the odds of a successful leap are much lower if there are parts of you still not yet on board.

When I went inside, I realized there were a few things I needed to set up for myself to be successful. First off, I cleared my calendar as much as possible for the first week since I still remember my last sleepless puppy nights. I also signed up for a puppy obedience class before he even came home, and made sure my dog sitter was on board with a puppy for our planned summer vacation. Will this mean it’s easy?  Definitely not. . . but it gives the possibility that once I’ve planned for barriers I can foresee, I can more easily tackle the challenges I didn’t see coming. 

So what’s your current puppy moment?

Is there something you’ve been dreaming about and wondering if the time is right?

Why not walk yourself through my five questions above and see what possibilities withstand some more inspection and introspection? Then you’ll know where it’s really worth placing your planning energy.

And don’t forget to drop me a line and let me know what you learned from these questions!

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Jo Ilfeld, PhD

An executive leadership coach, Jo helps C-suite leaders, executives, and high-potential managers develop the flexibility, skill, and frame of mind to meet the challenges of the next five, ten, twenty years…. and beyond. She works with individuals, teams and organizations on four core areas of leadership development. Check out Jo's bio page for more information.

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