From Selfie to Imposter Syndrome and Pursuing Your Dreams In Between

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This is part 1 of a series sharing my journey to land my dream job. I look forward to sharing this process with you as the days unfold it and thank you for reading.

Earlier this month, I posted this selfie (heh) to Instagram.

A few of my friends commented that I looked sad in it. I deleted the first comment because I was embarrassed by it but I decided to leave the second one up, along with the photo, because doing so felt honest. As a result of this particularly unusual meta Instagram experience, I realized my friends were right. 

I was sad.

I hated my job and the lack of agency I felt in not being able to do work I was passionate about was making my day-to-day disposition pretty bleak.

The day after I posted that selfie, I quit.

I requested a meeting with the Managing Director of the office I’d been employed at for five months and I told him, after weeks of being asked to reflect on the possibilities of my future at the company, that recruiting just wasn’t for me. I had taken the job because I valued the company’s vision and leadership, and it provided me with an exit from the non-profit space I was burned out by. I also knew it would be an excellent way to build my professional network in the digital media industry given the company’s specialty. My functional role in recruiting, however, left little opportunity for strategy-building, driving change, or program development – areas I had loved and thrived in prior to this role. I thanked my boss for the opportunity, applauded his talent for building a hard-working, friendly team of colleagues I didn’t want to leave behind, and packed my desk in order to be on my way by lunchtime.

The next day, I laid in bed absorbing the shock of what I had just done.

I reflected on times in the past where I’d taken similar leaps of boldness and landed on my feet. I encouraged my instincts on as I cycled through waves of anxiety that I had made a huge mistake. That day, I became my own cheerleader and coach, developing a strategic game plan while also delivering the most inspiring locker room speech of my life… to myself.

Between watching episodes of Being Mary Jane and picking at containers of take-out, I reflected on the job titles and responsibilities I wanted, regardless of whether I believed I was qualified for them or not. Managing Editor. Senior Writer. Associate Editor. Editor in Chief. I allowed myself to dream a little and all of my dreams lead me to a place where I would employ my leadership abilities, my research savvy, and my love for discourse within the internet community into an editorial position at a digital media company or news organization.

The following Monday, I reached out to several friends who are especially talented at writing cover letters and resumes, and asked for their best tips and examples. I took several ideas I had set aside for this site and began creating an aggressive editorial calendar to cement this place as one I could freely write in as I learn, develop my voice, and make (many) mistakes. Finally, I took a long look at my resume and capitalized on the communications experience I’ve had thus far, pivoting the breakdown of my skills in a way that would allow hiring managers to connect the dots between my previous roles and the direction I was newly determined to head.

I applied to over 25 jobs that day and immediately received three emails requesting follow-up interviews in return. Allow me to digress and point out that this kind of turnaround is HIGHLY unusual. I’ve been in the job market on and off for six years and have never experienced anything like it. In speaking to people much wiser than I am and reflecting on this experience, I’ve realized that a huge factor that determines success – one that we have very little control over – is timing. The paradox is that you won’t know when the time is right but if you keep waiting to act until you do, that moment will never come.

Friends who have witnessed my career trajectory unfold throughout the years have asked for insight on my ability to shape the experiences and opportunities available to me. It’s been absurdly encouraging to receive texts from friends this morning, sharing that my example has lit a fire under their own feet in the direction of their dreams. I realize the problem with “follow your dreams” philosophy as it’s repackaged to us in our modern world is it doesn’t account for how much work it takes. Not the cliches, or well-meaning “Top Ten Entrepreneurs Who Followed Their Dreams And Hit It Big” lists on Forbes. And by sharing this process with you, that’s exactly what I hope to communicate – that there’s no such thing as an overnight success or flash in the pan.

The reality of my experience is I make my mind up about what I want (admittedly, this one took a while), seek the advice of people who are smarter than me, and I start knocking on doors hard and long enough for people to hear me and open them. I figure if the timing is right and I’ve done my research, it’ll work.

This is the philosophy I used in securing a lunch date with the Vice President of Innovation and Engagement at a company I admire after I emailed him in interest towards a project they’re launching exploring opportunities for youth empowerment within journalism.

This is the philosophy I used when I reached out to a coach at my gym who also owns a restaurant and got the hostessing gig that’s keeping me afloat until I return to a traditional office space.

And this is the philosophy I used when I reconnected with the local alumni chapter at a national organization I’m a part of and enlisted to support in their rebranding efforts to gain more exposure to their network.

I have an interview in a couple of hours and an interview on Monday, in addition to a follow-up meeting with the CEO of another company I am interviewing with scheduled next Thursday. It would be easiest to keep this process to myself and let y’all know when I finally snag a job I’m excited about. Yes – it’s easiest to share the milestones in our life online when we can sum up the process without mentioning all of the tedious effort, moonlighting gigs, research, and strategic networking it took. But I wouldn’t be okay with perpetuating the lie of the #Luckygirl. It would be dishonest to say “got the gig! #blessed” and put a big bow around the delivery of the news as if it didn’t take a daily dose of humility, a stubborn sense of self, an eagerness to learn, and grace.

All of the grace.

To face rejection with dignity, ask for help, and have the courage to say (when necessary), “I don’t know but I’m going to learn at any cost.”

I’ve always held positions that specialized in a communications capacity but editorial is the untapped frontier for me. And over the course of five years, imposter syndrome has kept me from entertaining my desire to break into it or invest in my professional development within this area. After I posted that selfie, I decided – if imposter syndrome was going to continue terrorizing my energy and confidence in myself, then I would just embrace it’s presence in my life and become the best “imposter” I could possibly be.

Anyway, I couldn’t give any more attention to all of the reasons my dreams couldn’t possibly be realized.

I had work to do.