Entrepreneur to Employee: My Awkward/Exciting/Challenging Transition Back

I am scared and excited to share this.

Over a month ago I posted on Facebook that I wanted to share my story of going from entrepreneur to employee…and have faced massive resistance to hitting publish.

I appreciate everyone who posted and messaged me to encourage me to share this story :)


Well, late last year I experienced some of the bleakest, saddest, most despair-filled moments of my life. It’s hard to go back, and it feels pretty vulnerable to share publicly after making a fresh start.

Though, when I remember that perhaps you (or someone you know) is going through a major life transition and is in need of comfort, connection, and someone raising their hand and saying, “I know how you feel” it inspired me to keep writing.

This post is long, and goes into quite a bit of detail on my personal story and actual tips for making a work transition. So for those of you who just want the punchline…it’s this: you will figure it out. You can get through this. You may have forgotten that you are resourceful, resilient, and deserve to be happy…and if so, I’m here to remind you that it’s possible for you. Even if you have zero clue what to do next, I assure you that you will figure it out and when you do it will be gahdamn glorious.

My Present Work Life:

I feel more aligned in my work (and life) than ever before. I work at Shopify as a Course Producer. Right now, I produce weekly online courses for participants in the Build a BIGGER Business competition. I’m staring at the (magnificent) faces of people like Marie Forleo, Daymond John, Tim Ferriss and talented entrepreneurs who are experts in their field, helping them create online courses for competition participants (entrepreneurs who are generating between $1-$50 million in revenue per year in their businesses).

I’m surrounded by geniuses (ahem colleagues) who are humble, generous, kind, ambitious and incredibly dedicated. The work is challenging, fun and interesting.

We have a snack wall.

It’s basically my personal work heaven.

If I only I could go back and tell Gwen of late 2016 what was ahead. Oh, the relief and joy she would feel. My life is rainbow-y and sunshiny right now, though it recently felt like monsoon season.

My Rise and Fall in Entrepreneurship:

I have always dreamed of being a full-time entrepreneur. I bought into the message that you’re not a true entrepreneur if you’re side hustling and have a full-time job. I was mesmerized by the freedom, the excitement and unique challenges of being da boss. I had been a freelancer and side-hustler for over ten years, and usually had a full-time job as well. Slowly, I had been building up my personal brand, pivoting, failing, starting again, and always pushing towards my entrepreneurial dream. At the start of 2016, an interesting opportunity presented itself: I got laid off. I saw this as the perfect opportunity to go full-time in my PR & events business. I dove right in. For the first half of the year, I thrived. I worked with amazing clients, traveled the world for work and fun, and fulfilled a dream of co-creating and launching my own online course (shameless plug: It’s called The Media Method).

The challenges snuck up on me slowly, though it’s clear to me that these are my top four mistakes:

  • Working alone. I recently took the Myers-Briggs personality test and discovered that I am 90% extroverted (shout out to my ENFP’s). Although I had consistently heard the message that entrepreneurs should not be ‘lone wolves’ and work alone, I didn’t immediately join a coworking space, and I slowly fell into a pattern of not connecting with clients or peers in person (I was Zoomin’ all the time). I noticed my life started shrinking and it felt too late to stop the momentum.
  • Being too fancy. I hired a team to help me with different aspects of my business that in truth were not necessary at the time. I just really liked the idea of having a team. I have no regrets with who I hired (they’re all fabulous), but my ego was caught up in appearing bigger than I really was.
  • Worrying about money way too much. I was living a limiting belief of ‘not enough’ for most of last year. Even when I had more than enough, my brain defaulted to ‘not enough.’ This was so very distracting and painful. And it’s true that what you focus on you get more of.
  • Not having a vision or goal. I was way too ‘go with the flow.’ Prior to last year, I was insanely goal oriented and driven to reach any goal I set out for myself. It exhausted me and I became a burnt out workaholic. So I saw my entrepreneurial journey as an opportunity to relax a little bit on the goals.

The Catalyst to Consciously Switching from Entrepreneur to Employee:

I had resisted the inevitable for awhile. The subtle gut feelings that I needed to make a career change soon became blaring warning signs I couldn’t ignore.

Here are a few of the ‘warning signs’ I noticed:

  • I started to become a hermit. I worked at night, and slept during the day avoiding contact with most humans whenever possible.
  • Spontaneously bursting into tears (which was problematic at the times I did drag myself out for coffee with a friend and they had to watch the waterworks).
  • Eating all the donuts all the time (not for the joy of eating donuts, but for the rush of sugar and ‘numb out’ factor).
My drug of choice.
  • When I saw peers or friends on the street, I would panic (and try to avoid them). I had no interest in small talk and definitely didn’t want to talk about work.

Though the true catalyst to making a change was chatting with my mom. I met up with her for lunch one day and when the topic of work came up I broke down. She listened with love, and cautiously said, “You can’t live like this…” It was true. I was officially living in misery.

In that moment, I allowed myself to accept it was time to let go of the ‘don’t quit…persist’ message and rejoin a team. The thought felt like relief to me. It felt right.

So How the Hell Do You Get a Job These Days?

Seriously. I think the first thing I did was Google that. The last time I applied for a job was in 2014 and I got hired without a cover letter. I literally had to dust off my old resumes from an old computer and start building from what felt like zero.

Truth is, I could create an entire course (and perhaps I will) on every tiny step I took to make the transition. Though for now, I’d love to share my top three suggestions of tools and tips. If you want more details on any part of this process, email me at ge@gwenelliot.com.

Your Team:

You need an ‘A’ team of support to help you stay positive and avoid wanting to crawl under a rock and stay there. I recommend finding a small group of people in your life who are the most compassionate and supportive who could be willing to check in on you. I have three younger sisters who were there for me. And I connected with my friend Jelena who was going through a similar career transition, and along with our mutual friend Ali, we had daily check-ins (yes…DAILY). We were also doing the A Course In Miracles daily practice to help us build momentum of staying positive. There were so many others who I love (you know who you are!) who helped me crush doubt, cry without feeling judged, laugh when it felt impossible, and supported me in believing I could find this new path.

Job Searching Tools:

Here are a few tools I recommend:

  • I signed up to Katherine Meisner’s 7 Day email course.
  • Going to coffee with trusted A team members. You’ve gotta get out of the house :)
  • I bought a resume and cover letter template on Etsy (so I could try to enjoy the process of creating them.
  • This post by Danielle LaPorte about honouring the incubation period between opportunities.
  • Sarah Vermunt’s book: Careergasm: Find Your Way to Feel Good Work (which amazingly, I recently got to host the book launch party held at Shopify…talk about synchronicity)!!
  • Job sites (When I started, I used Indeed.com [the easiest one to use in my experience], Monster.ca, various media job sites.
  • LinkedIn
  • AngelList, Crunchbase (I’d look for companies that just raised a round of funding, which made me think they are looking to expand their team).

Tools for Mental Health:

Your state of mind is crucial at this time…here are a few ways I was able to stay positive:

  • Krav Maga (martial arts). Going to martial arts was an incredible stress reliever for me. It helped me feel like I was making progress in something.
  • I used the Calm app to meditate for a few minutes each day whenever possible.
  • Unfollowing anyone online who triggered me. Quite honestly, I almost unfollowed everyone I knew. I really tried to stay focused on my path.
  • See a therapist. I went to a therapist for one session. It wasn’t really for me, but I’m happy I went to explore.
  • See a spiritual therapist ;) Shawn Phelps is one of the most amazing women I know. Her work really helped me reconnect with why I’m here and trust the process.
  • Cut your expenses. Since thinking of money was something that kept stressing me out, I worked with my trusted financial advisor Shannon Lee Simmons to share what I was going through. She also provided brilliant advice for scaling back expenses (and she let me keep Krav Maga on the budget ;).
  • Go for long walks, ideally near water or in nature. This is super helpful in clearing your mind.

When I first started the search, I knew my self esteem had hit rock bottom and it was going to be a process to unravel the shame of ‘failing’ and believing ‘everything happens exactly as it should.’

I found my confidence started to build, the more I put myself out there and got feedback. Soon I found I had multiple job interviews. After getting to the third round of interviews at one company (including presenting to their CEO), receiving a job offer in PR at a hardware company, and a few freelance and full-time opportunities that didn’t feel aligned, I started to get a bit frustrated.

It was in this time that I came to the realization: It’s not about the job, it’s about living your life in alignment. (Coming to this realization could be another full blog post…)

So what does ‘living in alignment’ mean? To me, it means feeling healthy, generous and loving the majority of the time.

I had always secretly hoped that something outside of myself would solve all of my problems. Though, I now know with deep conviction that the work to be happy and fulfilled is all internal. Once you feel good, you start attracting aligned opportunities.

With this realization, I did something counterintuitive: I took a break.

It was holiday season, so I decided to put down the job push and enjoy some time with my family in Beaverton (my quiet hometown). I focused on doing activities that made me feel better and stay positive. I would only apply to jobs if I felt a strong impulse to go for it.

And on January 1st it happened. I saw the job posting on Shopify.com for the Course Producer role. When I read the posting all I felt was: YES!

Little did I know I was about to embark on an almost two month process to get hired. The A team was crucial at this time. After six interviews (four in person, two on the phone) and killer words of confidence from my references (thank you Katherine Hague and Sean Wise), I was hired. I started on March 6th, 2017.

To conclude, I have truly been humbled by this process and now that I reflect on it, I so appreciate the journey. It was awkward, exciting, challenging and for the love of God, I’m glad it’s over ;)

Now, I’ve been launched into a new line of work that’s incredibly joyful, fun and has the potential to make a real difference for people now and when we launch courses to the masses later this year. Also, my entrepreneurial spirit has been completely reignited. I’m 100% back to being a side hustler and loving it.

But of course, I try to remind myself everyday (especially the two times I’ve been experiencing migraines or feeling sick since starting the new gig) that happiness and fulfillment is an inside job.

It’s all about cultivating the feelings I want to feel (happiness, ease, generosity, flow) and not relying on my job, a relationship or anything outside myself to give me these feelings.

I really appreciate you reading this. If you have any tips about making a transition, I’d love to read them in the comments or feel free to email me (ge@gwenelliot.com) if you need a compassionate ear to help you through one of life’s speed-bumps.

We’re all in this together ❤.