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Some Fresh Air and Fresh Perspective on My Career

   Posted On: October 19, 2017  |    Posted In: Career  |     Posted by: Broke Millennial®

This post is sponsored by SoFi & photo courtesy of SoFi 

Last weekend I boarded a bus to get out of New York City and smell the fresh countryside air for a few hours. Okay, countryside may be pushing it, but non-New York City street smells. The quick, day trip was for a career retreat at the Grounds for Sculpture in New Jersey, courtesy of SoFi. The one-day SoFi Accelerate career retreat was offered to SoFi members for free as part of its community events (I attended as a guest of SoFi).

The program had previously been put on for SoFi members and member’s guests in both San Francisco and Chicago. It was a full day affair with the intention of helping already highly motivated individuals push forward in their careers.

As a self-employed individual with occasional bouts of crippling self-doubt about what’s next in my career, I leapt at the chance for a free trip to a new place and a little guidance. I was also seduced by the fact that Coss Marte of ConBody would be speaking. I’ve been following Marte’s career since he was profiled in the podcast StartUp (but I’m still way too intimidated to actually try the ConBody workout as I think it’ll end up with me in the fetal position trying to avoid showing my latest meal to the entire class).

But I digress.


The day started with a complimentary breakfast while the buses pulled in bringing SoFi members from New York, New Jersey and Philadelphia. We all received name tags with a shape next to our names and a color coded lanyard. These shapes and colors were later revealed to correspond with our with tendency (color) as defined by Gretchen Rubin and career goals (shape) .

I was a hexagon, which meant I felt settled in what I was doing career wise but stalling on how to advance, and the green lanyard meant I was an obliger, someone who meets outer expectations (just give me a deadline and I’ll meet it), but resists inner expectations (snooze that alarm).

We spent the day working through various exercises and speaking to those who were grouped similarly, in order to help established something of a career vision board and mission statement. Honestly, my biggest takeaway was learning that I’m an obliger. That’s an intensely difficult internal pull for someone who is self-employed and therefore needs to be self-motivated. In order to circumvent my obliger instincts, I realized hiring more people on my team would be helpful to keep me accountable.

The group was released for lunch where we had opportunities to network. You could sit based on industry (e.g. Finance, Healthcare, Non-profit) if you wanted or just branch out. I sat at a finance table and got into some interesting discussions about the FIRE movement, why parents keep raiding their retirement accounts for college-aged children, and career goals. Then we headed back for the much-anticipated panel discussion.


Coss Marte and John Coyle, author of The Art of Really Living shared their journeys as entrepreneurs. Coyle dropped a bomb when he said, “know when to quit.”

I wanted to run up and give him a high-five.

So often we’re taught this idea of pushing, pushing, pushing until we finally succeed, but that isn’t always going to happen! Instead, Coyle recommended a two-year rule. Stick it out for two years because in year one you are likely still getting your bearings, but if moves aren’t happening in year two, then you need to consider making it (your entrepreneurial endeavor) a hobby or moving on entirely.

Coss spoke right to me when he said his best advice is to remember the words of his mother: “you don’t ask, you don’t eat.” Considering that my mother told me how to “ask for the order,” I immediately connected with his story. Coss also shared a Silicon Valley (the TV show) style pitching tip: “I take Uber Pool so I can be pitching ConBody to my fellow riders.” #Genius.


It was an inspiring day, but now the onus is on me and all the other attendees to actually make something of our key takeaways. To be honest, my career goal vision felt so lofty I was fine sharing it with a perfect stranger but I’m apprehensive to broadcast it publicly right here. Maybe that’s because I’m an obliger and having people out there holding me accountable will make it too real! In the meantime, I’ll be meeting other deadlines and figuring out how to hack my tendencies in order to be more productive as my own boss.

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