How My 21-Year-Old Self Taught Me to Beat Imposter Syndrome

She was fearless.

Ashley K. Stoyanov Ojeda
3 min readJul 16, 2020

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Photo by Slava on Unsplash

At 21 years old, I had just entered my “reclaim my power” phase after being in a toxic relationship with a much older man. Jack Daniels was my sidekick, the college pub bartenders knew my type and while there were many things I could have made better decisions about back then — there was one thing I never hesitated about.

I trusted myself. Always.

I always thought that I knew what was best for my life and I just went for it. I dated whoever I wanted, I published whatever I wanted on my blog, I sang Ke$ha covers and went dancing every weekend. I expressed myself wherever and whenever. I was absolutely fearless.

Granted, there was a lot I probably should not have done (but um, #NoRagrets?) and while there’s a laundry list of things I wish I could tell my younger self, up until recently, I really just envied her.

At 28 years old, I’ve learned a bit more about how the world works and have felt fulfilled thus far in my professional and personal life. I’ve helped build startups, I founded a nationwide nonprofit, I coach creative entrepreneurs on how to grow their businesses. I’m a leader within my communities, I’m happily married, have a great relationship with my family and yet as I became more and more self-aware, a part of me started to fill with self-doubt. For the first time in my life, I was getting very familiar with imposter syndrome and it was getting pretty ugly.

Life was getting better across all boards. My career was coming together just as I had always wanted. After dealing with chronic illness and recovering from a bad car accident, I started feeling better than I’ve felt in years. My marriage is happy and we are connecting better than ever.

21-year old me would likely be shocked if she knew everything we’ve overcome in the last few years.

But, as we’ve all heard before “With great power, comes great responsibility.”

As I processed everything that was happening, started to look at my goals for the rest of the year — I just kept thinking “What if I can’t figure this out?” and the more prominent, “What if I f*** something up?”.

Somehow between all the bullshit of adulthood and responsibilities and expectations — I had become cautious — maybe a little too cautious. I was scared of experiencing my 3 AM bursts of creativity, scared of my spontaneous business pivots and plans, scared of expressing myself through song, scared of writing just to write — I had become afraid of every part of myself that has made me successful.

I had lost a little bit of that fire I had at 21 when I felt like I had to prove myself. But then, one day I found an old journal where I wrote about all of my shenanigans. I remembered what it was like to feel like I had nothing to lose. I remembered what it was like to feel free.

Recently during a coaching call with a client, I was reminded of all of this as I helped her get through her own feelings of imposter syndrome. I said to her that the moment you decide to become an entrepreneur, a community-leader, start a new relationship, or make any kind of big move — you are putting yourself out there. And you have to get comfortable with the idea that you will not feel comfortable all the time.

So how do we block out all the noise? How do we deal with imposter syndrome?

We have to learn to trust ourselves. Trusting that we know exactly what we’re doing and that we’re doing everything at the right time and for the right reasons. And if we do that, we can be fearless too.

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Ashley K. Stoyanov Ojeda

On a mission to create opportunities for underrepresented creators and entrepreneurs. I write about business, growth and my feelings. www.ashleykstoyanov.com