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The Most Common Fears That Prevent Corporate Leaders from Chasing Their Dream Job

There’s a small voice inside of you that has a dream to do something other than what you’re doing now.  Occasionally, you give yourself the time and space to imagine what it would be like to chase your dream.  But for the most part, you ignore your dream because along with that dream comes fear.

I’ve connected with hundreds of leaders over the years who reached out to take one step further in exploring their career dream.  There are many success stories from those clients who have decided to actively make a change in their career (just check out my testimonials to see for yourself).

But there are also numerous stories about those who have reached out, in a spark of optimism, but were pulled back into their day to day.  And some reached out again down the road because that dream never went away.

Rest assured, when someone chooses to work with me, those fears don’t magically disappear.  They come up again as fears and obstacles.  But once we’re able to find our way past these fears and remove the block, magic happens.

Over the next couple weeks, I’ll be diving into the most common fears that prevent corporate leaders from playing big and chasing their dream job.

If you have been thinking about a career transition, whether it be to make a shift in your job responsibilities or taking a closer look at your leadership style, my hope is that the insights from all of those who have swam these waters before will provide you the answer you need to decide if you’re ready for the next chapter.

Change can be uncomfortable.  But when you get to a point when you know you can’t stay where you are any longer, whether that be in a metaphorical place or physical place, the need to seek change no longer becomes an option, it becomes an imperative.

By looking closer at the fear that is driving your inclination to stay safe in the place where you are, dissatisfied or at the best, content but not inspired, you will find what you need to decide if you’re ready for the next chapter.

The reason I love working with corporate leaders is because they have a track record of success.  Which means that, when they are appropriately inspired, they can move mountains to reach the goals that they set.  And typically, the goals they reach have a ripple effect on the many, many people that they touch in their lives.

Let’s help you shift from focusing on the challenges on your beautiful dream and instead, on the potential positive impact.  The world is waiting for you.

Fear #1

Is it possible to find a job I like and maintain my lifestyle?  Does anyone who makes a lot of money actually like their job?

Money is an important variable to consider in any career move you make.  It’s a finite resource and it allows us to secure items that provide security and comfort in our lives.  However, if you’re asking this question, I’m guessing that money isn’t the top driver behind your desired change.  But it may be the one that keeps you where you are.

To directly answer the question- there are lots of people who make a lot of money and like their job!   I often find the best way to get past this fear it to suspend the concern while you focus on exploring your dream.  What typically happens is a pendulum swing.

You may start looking at radically different options to ease the pain you’re feeling now.  But as you get further into your conversations and search, you will eventually come back to a place a different from where you are now but not so drastically far away that you can’t still leverage your skills, education and experience to command pay similar to what you’re making now (if not more).

I’ll share my personal search as an example.  In my last corporate role, I was Director of Marketing for a rapidly growing healthcare nutrition company.  I liked the work I was doing… but I didn’t love it.  But the money was really good so I stayed.

This led to a significant amount of personal stress in my life: my job continually required time away from my family, I harbored a high amount of daily frustration as my top values were not honored in the career path I was on, and this excess stress overflowed to a point where I didn’t like the way I was showing up, at work or at home.  I was far from where I wanted to be from a career and personal perspective. 

My journey started as a need to ease the pain and led me to hire a coach because I didn’t feel like I could do it on my own.  By starting there, and with a goal focused exclusively on building a more fulfilling life, I found that my calling was to coach corporate leaders (but before this, I explored becoming a yoga instructor, a real estate agent, a chef, and a franchise owner). 

Every time I focused on the money aspect, the fear returned.  I had to trust myself, the process, and believe that a higher power would guide me in the right direction.  And it worked- I am happier in my career than I have ever been, all around.

Almost every single client that I have worked with who was at a senior level in their career has been able to pivot to a more fulfilling role or was able to see their current role in a new light, that led to greater fulfillment.  But the shackles of the fear must first be addressed and unhinged and the excitement of the potential next step elevated.

To do this, here are few questions to explore:

  1. What would your life look like five years down the road if you stayed where you are now?
  2. Twenty years from now, if you were to come back to have a conversation with your current self, what do you think you would advise?  (If you struggle with this, think about what your current self would have told your past self twenty years ago and use the same logic)
  3. If you knew your last day on earth was next week, what would you do differently?

All these questions are pushing you to isolate and understand what truly matters.  And spark some urgency.  The best time to plant a seed was 20 years ago.  The second best time is now.  Don’t let life pass you by by letting fear guide your decisions.

A caveat to this: there are very good reasons for prioritizing money so please don’t misinterpret this as criticizing those who decide to do so.  The key is to make a conscious choice and find peace in your decision to do so.  Once you do, it is no longer fear making the decision, it is your own free will.  And that will shift things substantially for you.

Imagine if Steve Jobs had taken the safe route and finished his schooling at Stanford and gone on to take a stable tech job instead of dropping out and starting Apple in his garage.  Or if Oprah had stayed in her local Chicago news casting role instead of seeking out a role in The Color Purple and eventually, starting her own talk show.   You’ll never know what the possibilities are until you start to suspend fear and explore your dream.  There is a way to do it without losing your safety net.  Slowly and consistently, focused on the dream rather than the fear, can over time lead to career fulfillment. Or you can take the plunge in one foul swoop! It’s all about finding your level of comfort to spark your motivation.

Fear #2

Am I qualified for the role I really want?

I’m going to be really candid and tell you straight: I don’t know if you’re qualified for the role you really want.  If you’re a Marketing VP but you really want to be a marine biologist, it’s likely that you don’t yet have the credentials that would make you a viable candidate for that job. 

But typically career desires don’t swing that far from center (sometimes they do!)

Most of the time, when I hear this concern, it’s when candidates are thinking about applying for a role that is only slightly different than the one they’re already in. 


When they read the job description and don’t have every single requirement, they automatically assume this discounts them from the role at hand.

An important statistic to remember when you start to go down this path: According to an U.S. Bureau of Labor Statistics and Yale University report, 70 percent of all jobs are found through networking.  If hiring managers were solely focused on only finding a candidate that checked every single requirement on the job description, this number would be much lower.

As you uncover opportunities, remember that the job description you are reading is a wish list for the perfect candidate.  But if you have a good rapport with the hiring manager or if you are the strongest in the pool of candidates who are ready and willing to take the job, then odds are that you’ll get the offer.

The trick here is not to take yourself out of the running before you’ve even tried.  And for roles and positions that you’re really interested in, do your best to find a way to network your way into the interview process instead of blinding dropping a resume and crossing your fingers in hopes that the bots pass your resume through to the right set of decision makers.

Fear #3

Will I let my team/coworkers down if I leave?

The undercurrent of this fear is a strong sense of loyalty.  And loyalty is a beautiful value.  But giving it too much energy can inadvertently prioritize the needs of others at the detriment to caring for your own needs. 

Oftentimes, this thought serves as a distraction or an excuse to avoid change (for other deep-rooted reasons typically driven by fear) but stems from a place of deep caring for others.

One of my clients, we’ll call her Adelaide, had a beautiful dream to open a center that provided skills and opportunities for underprivileged women.  She was already working for a foundation that touted itself as a nonprofit where people could go to advance their network and their leadership skills.  But it catered to the upper echelon of society, those who had money.  Her dream was to take this same service and offer it to the masses.

But her strong sense of loyalty prevented her from leaving her current role.  She was unhappy, and worked hard to make her company a better place to work but the politics and internal motivations of the organization were consistently at odds with her values.

In one eye-opening session, she suggested staying in her current role and satisfying her need to help the audience she was most motivated to support through volunteering.  The challenge was, her plate was already overflowing.  So adding to it was not the answer.  But she couldn’t bring herself to envision leaving the role that was leaving her drained and unfulfilled.

As we dug into this, at the core of her hesitation was this strong sense of loyalty.  If she left, she would let down her team members who so relied on her to do her job.  She couldn’t bring herself to envision a future that resulted in her leaving them high and dry.

If you sense that loyalty is at the core of preventing you from pursuing the change you desire, the trap you’re likely falling into is that you are only focusing on helping others win without an eye to your own win.  So you’re trapped in a win-lose scenario.

What would a win-win look like? 

Encourage yourself to envision a scenario where your team/your co-workers come out on top… AND YOU DO TOO. 

For Adelaide, it became clear that her leaving could open up opportunities for her co-workers that might not have otherwise existed.  Perhaps they would be promoted into her role.  Maybe they would also find the courage to leave.  Perhaps her leaving would be the final straw after a string of departures that would motivate management to make changes for the better for everyone else.  While she could pursue her dream.

Once clients get past these fears, the path forward tends to be filled with career fulfillment and personal satisfaction. I look forward to hearing what happens when you put the steps in motion to pursue that career dream that’s been dancing around you for quite some time.

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"After working with Amy, I feel confident that I know what I am meant to do, what my career goals are, and how I am going to achieve them. Read more."

Leslie, VP of Marketing at a Tech Company
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