Overwhelmed with imposter syndrome? Tell Yourself What You Need.

By the end of 2016, I realized two very important things.  First, I’d had the most productive and successful year of my career.  Second, I was rapidly plummeting into a phase of deep burnout.  Like most people, I didn’t realize I was burned out.  I adopted an all too familiar “keep making lists and power through” mentality.  It wasn’t until this episode of The Broad Experience made me cry on the way into the office that I knew something was wrong.  I took several courses of action to get myself out of burnout, but one of the most transformative was taking on a co-director for the non-profit I started in 2015.  Gabby is a force of nature: smart, innovative, and emotionally authentic.  She also happens to be 6 years younger than me and has spent her entire post-college phase in the throes of our culture’s glorification of entrepreneurship.  One of the joys of working with Gabby is the opportunity to share what I’ve learned running my business over the past 9 years and watching her develop her own leadership voice.  In one of our recent meetings, Gabby and I began talking about all the entrepreneurship advice she’d been seeking out - podcasts, books, articles, coaches - and eventually asked me an essential question that every entrepreneur battles with: how do you get over feeling like you’re not good enough?  First I laughed (because I still don’t think I’m good enough) and then I verbally processed (read: word vomited) for a long time, telling stories of bad business decisions and personal doubt.  She responded with shock and told me she would never have guessed I’d experienced that level of self-doubt.  I began thinking about my own struggle with self-worth and I wondered - why is it so hard to believe that entrepreneurs are just people with a job?  

For the first 6 years running my business, I did so largely in a vacuum.  

I didn’t know many other entrepreneurs, I wasn’t aware of meetups or online groups or blogs - partially because I worked from home and partially because they didn’t exist.  When I first started in 2008, my generation was just at the beginning of building the culture that would eventually glorify business owners as celebrities.  In 2008, my friends were graduating college, still under the assumption they’d get jobs in their chosen field.  I didn’t start a business because I was socialized to do so, I started a business because there was nothing else I wanted to do with my life.  Over the past 3 years, I’ve hired more staff, joined a co-working space and grown my network of entrepreneurial peers.

Now that I interact with other entrepreneurs more often, I’m always thrown off and a bit embarrassed when people at the beginning of their journey ask me questions like: how did you know you’d be profitable, or how did you know when it was time to scale, or how did you learn to manage your self-care?  Even their questions make me feel like I failed at something.  In my head, I can picture myself at 25 years old asking my friends to buy me $2 beers at dive bars because I was in the middle of “Debbie’s Punk Month”, a term coined by a friend for when my business and I ran out of money in August every year.  I didn’t decide when it was time to scale or manage my self-care, I quite simply could not afford to not be good at this and so I kept trying to get better at it until I was able to pay my bills.  I learned whatever I needed to learn to keep bringing in more business, in whatever way I could.  

Today, I’m inundated with content marketed to me (entrepreneurial late millennial) and I’m constantly having epiphanies (Oh, THIS is how REAL businesses owners do it!).  And, of course, now that my company has more resources and staff, I do sit down and think through strategies based on things I’ve learned from content targeted to me.  But as I listened to Gabby talk through her insecurities about what it meant to be the owner of something, it struck me that there’s a breaking point of how we interact with this advice.  

In some ways, we are killing ourselves with how-to content.

The truth is that the most valuable skill you need as a business owner is your ability be comfortable not knowing the outcome.  And that’s a skill you only gain through constantly practicing discomfort.  Every millennial entrepreneur I meet is bombarded with webinars, blog posts, e-books, and checklists outlining the step by step process of starting and running a business.  For reference, I’m writing this at 1:32 pm and already today I’ve received newsletters teaching me step by step ways to stick with my goals, be more authentic online, take more beautiful Instagram photos, be more confident in my body, lose weight and keep it off, and (my favorite) be happier.  Of course, this is the world we’re all living in.  Right now you’re reading entrepreneurship how-to content about how to care less about entrepreneurship how-to content.

There’s value in the amount of information that we can access.  I can learn almost anything I need to know about business through a curated series of webinars, which is truly incredible.  There’s nothing wrong with learning the tangible skills that make navigating business growth easier.  The problem comes in when reading how-to content begins to distil and ignore the very real and personal struggles of the author.  Just because someone wrote a listicle about how to turn your side hustle into a business and didn’t include the crying, health issues, relationship impact, etc. that went into their growth doesn’t mean they weren’t there.  When the subtext of distilled advice moves from skill building to facade building, that’s when it starts to trample our confidence.  

I think it’s important to remember that your business and yourself aren’t separate.  Starting and running a business won’t be as simple as a checklist of tasks and allowing the internet to make you think it is will crush your ability to be effective.  Your business endeavor does not exist in a vacuum. It will be one piece of you, while the other pieces are figuring out how to navigate romantic relationships, give advice to your friends and family, decorate your apartment, grieve losses, cook meals, feed your pets, have children, take vacations, pay bills, and so on.  

Figuring out how to run a business is just as simple as figuring out how to overcome loneliness or fear of rejection or imposter syndrome.  

These are struggles that are always with us, constantly reacting and intersecting with the events and people in our lives, and ever fluctuating as we grow and change.  Work/life balance has, of course, been debunked.  Life is a balance of all that we choose to put in it and there’s no way of knowing what will happen or how these pieces will intersect with each other.  

In a way, I’m glad to have started a business before the noise of the entrepreneurship movement was filling my inbox.  I was blissfully unaware of how poor of a job I was doing in comparison to others. And in this way, I was freer to assess what I actually needed.    

My advice to Gabby - and to myself - is to challenge yourself to choose your own consumption.  

We’ve allowed ourselves to believe that happiness is in the achievement of the goal, but if you pay attention to the truly happy, you realize the “big win” is whether or not your job fills you with joy and purpose.  If you start by asking yourself: is this job making me happy?  And if not, what would make this job more fulfilling?  Often, the answer to that question guides you to the exact advice you need.  Truly, the thing you might find you need is quiet, or a therapist, or a healthy meal, or a night out drinking with your friends.  When we allow outside sources to tell us what we need to do a good job of running a successful business, we begin separating and suppressing the other parts of ourselves that are treading water alongside our career.  When I ask myself what would make my job more fulfilling, the answer often really is seeking out advice or help from experts in a certain area.  The big difference is that when I’m seeking that help in response to the question of what would make my job more enjoyable, it comes from a place of what truly matters to my whole person.  

EssayDebra Giunta