Feeling Like You Don’t Measure Up? A Career Consultant on How to Let Go of a Timeline and Trust Your Instincts

My twenties were absolutely dominated by a type of girl-boss-meets-going-for-broke definition of real success. Lean In, the Sheryl Sandberg sensation, was published just months after I graduated from college. And though my English degree wasn’t exactly launching me into the tech world, the book’s ethos—that women can achieve it all if they work hard enough—pervaded every professional field. That same year, Blake Mycoskie, a college dropout from my own alma mater, was reportedly making hundreds of millions in sales with his shoe company TOMS—all at the ripe age of 37. And just a couple of years prior, the Oscar-winning film The Social Network painted a picture (if not always flattering) of a modern, hoodie-clad success story forged in a college dorm. To say it was time to redefine success is, well, a massive understatement.

Now fully ensconced into my 30s, and well past any visions of launching a Glossier-type empire out of my parent’s garage, I occasionally grapple with the idea that I’ve failed. As though I’ve missed some sort of golden entrepreneurial opportunity to reach my fullest potential. That I’ve submitted to a sad existence as a—gasp—employee.

But then I get a grip. Not only because career success, at its core, should be defined by getting paid to do something you enjoy, but because there are so many stories that break the millennial-minded mold of what a fulfilling, influential career should look like.

Featured imaged by Michelle Nash.

Image by Michelle Nash

How You Can Learn to Redefine Success

Take, for example, Amy Liu, who founded the clean skincare line Tower28 at age 40 (with three small children and a mortgage) after years of working for companies and eponymous brands like Smashbox and Kate Somerville.

“I was an employee,” Liu shared with Create & Cultivate founder Jaclyn Johnson on the Work Party podcast. “I had a really linear path. I went to business school. I worked my way up in the beauty industry. It took me 18 years before I started doing this.”

She later notes that working in the same industry for a long time also helped her when striking out on her own. “I had a community and knew who the players were,” Liu said.

All of this is not to say that to achieve true success means you have to be your own boss or launch a brand. For starters, not everyone is cut out to be—or even wants to be—a boss. So, to get a more thoughtful understanding of how we should be defining (or redefining) success, I spoke with transformative coach and consultant Jessie Douglass-Smith McGraw.

Image by Belathée Photography

The Benefits of Taking Career Risks Later in Life

More than anything, as people go down the path of life, they tend to get clearer on what’s important to them. They understand better what their passions are, and what lights them up. It comes from a deeper place of authenticity, a soul-pull if you will, versus from an ego mind full of conditioned ideas around what will bring them the most money, notoriety, or power (on a deeper level: safety, security, and belonging). And in doing so, they experience a feeling of alignment in ways that are incredibly fulfilling and that impact every area of their life.

It comes from a deeper place of authenticity, a soul-pull if you will, versus from an ego mind full of conditioned ideas around what will bring them the most money, notoriety, or power.

Incidentally, when people start a company or new career from this more deeply aligned place, they tend to find major success (or success finds them). They have already experienced fulfillment by belonging to themselves, to their desires, and to what’s good for them, which unveils the feeling of safety and security from within. The money, notoriety, or power ends up being icing on the cake and even humbling.

Image by Ka Vang

Is there a sweet-spot age for taking a career risk?

Absolutely not. I have had clients make incredibly successful and daring leaps from ages 19 to 70. The most important factor is following one’s own instincts, the quiet voice inside that is giving the next indicated step. Humans tend to get caught up in ideas of how fast things should be happening. They monitor how they are doing and measure it against the idea in their head of where they think they should be. This often leads them to feel like they’re falling short, which lowers their professional self-worth and ultimately makes them doubt their potential.

But with their gaze turned inward and away from the noise, everything is possible.

On the Pitfalls of Autonomous Early Success

This isn’t the case for all young folks, but more often than not, they were driven to that success to make up for something that they feel is missing inside, a feeling of emptiness. So their ego—the conditioned ideas in their head of what will bring them the most money, notoriety, or power (on a deeper level: safety, security, and belonging)—is the driving force that ultimately leads to burnout, lack of deep fulfillment, narcissism and a sense of self-importance.

Why narcissism and self-importance? When we build our lives on a foundation of insecurity, anything and everyone becomes a threat to the success that was built on that foundation.

When we build our lives on a foundation of insecurity, anything and everyone becomes a threat to the success that was built on that foundation.

Image by Teal Thomsen

On Feelings of Hopelessness About Your Career Path

First, do a gut check…

Are you pursuing your current career because you’re keeping up with an idea in your head that it’s what you have to do or should do to be successful? And that success is what you need in order to be fulfilled? If so, your hopelessness is being a friend—one who’s trying to wake you up to the fact that you’re belonging to someone else’s idea of success and fulfillment, not your own.

Step 1: Appreciate Where You Are

Do you love the career you’re pursuing? Congratulations! Firstly, it takes courage to honor your own voice and path, to break the mold at any age. Take a moment to appreciate that.

Step 2: Listen to Your Gut

Second, be mindful of the mood you’re in when you’re taking stock of how you’re doing in your career. Our moods, 100% of the time, impact how we see ourselves and how we see our life. If we’re in a low mood, things don’t look so good. When our mind settles and our mood rises, life looks full of potential and possibility again.

Step 3: Honor Your Instinct

In this case, your hopelessness is once again being a friend, letting you know your mood isn’t great. So pump the breaks on assessing how things are going, turn your gaze inward, ask yourself what you want to do next, and honor what your instincts tell you. One foot in front of the other and you will find yourself back in the saddle again.