Career Tip: #Rethink Yourself

Disclaimer: This post was originally published in 2012. But! I firmly believe the tips shared are still relevant today.

I’ve just returned to my desk after hearing a butt-kicking #Rethink presentation by Charles Day, evangelical entrepreneur and consultant, at one of my favorite workspaces in New York called Grind

I’m not a morning person, try as I might, but I’ve been in need of a worthy wake up call and Grind is one of the few spaces that truly offers value in every way for the independent beings like myself. So, I got up before dawn and headed out in anticipation of a good morning pre-work lecture.

My career years aren’t getting any easier. It’s the end of 2012 and it’s been difficult for me to define my successes while forgetting my failures. I have been incredibly disappointed in a majority of outcomes with the projects I launched (and then never went anywhere), the people I’ve worked with, and certainly the sacrifices I’ve endured in an effort to get things back on track. 

Charles Day’s #Rethink Yourself proposed some hard-hitting questions, and as my friend Briana Campbell (of Work it Brooklyn) and I sat there listening, we both kept sighing, knowing we had more questions than answers to fill.

So, I have some homework to do. It seems being entrepreneurial-minded, I’m constantly facing more challenges than solutions. This year’s biggest challenge: should I give up freelancing to pursue a full-time salary job? Spoiler: Yes. presented many realizations for me, of which I have yet to confront. 

Earlier this year I wrote about work/life balance in lue of Hurricane Sandy. Quality of life is an issue I have felt strongly about for a long time - and still have much more to say on - as I continue to battle my phone notifications, email alerts, and ever-growing to do lists head on. But I’ve been trying to take a step back and analyze what would make me happy:

What’s my story? What is my purpose? Why do I exist? Why does the work I do matter? The questions asked above by Charles have been the same questions I’ve been fighting all year. 

Yesterday, I tried to make a 1% improvement (see Day’s presentation to learn more) on productivity, by turning off all phone notifications. That lasted only a few hours before my phone rang with a new deadline on the other end. There, I asked myself: If I stopped freelancing, and worked as say, an Account Executive (which I basically do now) on the same number of projects (on average I have 3-5), but with a 10am start time and 6pm end of day, instead of my usual 9am til whenever I pass out on my bed, my stress level would be just as high. My phone would still go off with emails, calls, texts, and urgent messages requiring my immediate attention. The “on call” assumption would still be there. Just because I was confined in an office for eight hours a day wouldn’t mean I’d be off the grid any other time. Many people live on this day-to-day schedule, and I have too for about four years now, but am more miserable than happy on any given week. I don’t know how much longer I could keep up.

And that’s bad. This weekend I felt guilty for having a weekend. Meaning, I didn’t spend all of Sunday working from my desk. Instead I did what normal people do - relax. I cooked, I watched TV, I spent time with my boyfriend. Am I wrong for enjoying that?

Define Success

Charles says to be as specific, honest, and selfish as possible. What do you want to get out of yourself and your business in the end? Do you want a million dollars? Do you want to be able to take care of a family? Do you want to leave behind a legacy? Right now, success to me means NOT being a 30-year old who still relies on her parents for money when rent is due. On a macro level, I want financial independence. I also want location independence. 

Define Purpose

This is difficult as I recently reviewed my archive of work and realized there are very few projects I can legitimately back as a successful use case. Everything else has fallen apart, or been abandoned, or folded in some capacity. Naturally, my confidence has plummeted as I enter more conversations and interviews unable to highlight achievements. How have I contributed to this? What have my project contributions led to? How have my skills led to real, impactful, profitable results? What objectives did I meet? How was my role crucial to the company’s growth and ultimate success? I have yet to find out. I always have the best, positive intentions and hope when I enter a new project but more so lately, things turn sour very quickly and I’m left feeling defeated. 

Tell your story

Last Friday I had a great coffee session with one of my go-to food & media friends, Nichelle Stephens (of Cupcake Takes the Cake fame) who left me with the joke, “We keep the hustle at 100” - meaning we never give up the search for bigger, better work and the money that comes with it. She and I have both been freelancing for a while and we discussed the vicious cycle that comes with the uncertainty of the next check. Without hustle, I wouldn’t survive. It’s all I know, and it’s been my story since day one. 

Introspection is a living, breathing process. When you remove yourself to take a look at the bigger picture, you’ll realize nothing is concrete. All I can hope for is the energy, motivation, and positivity to keep going. Perhaps my end destination will payoff to the long, hard road I’ve faced. 


The End of an Era: A Freelancer's Failure Story

What Hurricane Sandy Taught Me About Work/Life Balance