Taking a Leap of Trust: Emily's Journey

This is a special in-depth profile covering Emily Lily’s career transition, which is part of a weekly “Give and Ask Day” in Cedar Lodge.

About Emily: In 2019, Emily left her job as Director of Culture to take an intentional pause from the corporate mindset. Breaking away from her 9-5 stresses and demands opened up opportunities to improve her health, travel to new countries, visit family, and spend time helping animals. She recently founded Coco’s Garden Sanctuary after the loss of her dog, Coco, and spends time volunteering with Portland Dachshund Rescue. Emily is also a Leadership & Culture Consultant, Life Coach, and Reiki Practitioner.

Megan: You underwent a big career transition last year. Can you share a little bit about how you knew it was time to move on and how that showed up in your body?

Emily: It's so different to look back on it now that I'm on the other side, and I think intuition played such a huge role in this decision. The intuitive feelings started coming quietly at first. I’d think to myself, "This doesn't quite feel right. There's something about this that isn't quite working." And of course, I completely ignored that and pushed forward. My ego and my intuition started having a little battle in my head, and it was a very confusing time.

I would say intuitively, “I feel like this is wrong. There's something about this that isn't right for me,” and my ego would say, "Oh, but you love the people and the people love you. You make good money. You have steady employment." I kept trying to prove myself wrong. I knew that it wasn't right, but I kept trying to prove that feeling wrong. It was at least two solid years of me going back and forth like this.

Then my body started responding, and I started to get extremely tired. I remember it being like a fight to try to get myself to work. And then after work I would just crash. It was like my body was sounding the alarm because I wasn't getting it.

I enjoyed my job. I deeply loved the people I worked with. I loved my boss. And he was one of my biggest supporters. The stress that I felt was intuitive stress. I can compare it to being in a relationship that you know is wrong for you. The person that you're with might be wonderful, and you love them and they're kind and you have fun with them, but you know that it's wrong. And maybe you can't put your finger on what exactly it is. But that's the magic of intuition - I may not know exactly why this isn't right, but I know it's not.

Once I started to get that extreme stress that manifested as exhaustion, I knew that this could not possibly be the right thing. I was exhausted every day and would force myself to get in the shower and drive to work, and the whole way there I'm thinking, "I don't want to do this." It's totally normal to have days like that, but every day was like that by the end, and that can't possibly be healthy. It wasn't healthy for me.

Megan: Once you came to terms with that, what were some of the things you used to figure out how to leave, and when to do it?

Emily: I started to pay a lot of attention to alignment and timing. And that felt important to me because I tend to be fairly impulsive, and I tend to want something and want it right now. But this was way too big of a life choice. So even though I was hurting and my health was not great, I had to start envisioning how I would do this - how could I make this work in a sustainable way?

One of the things that happened that felt very serendipitous was when a friend referred me to you. You were offering six months of career coaching, and I immediately knew that that was the right thing, because there were so many people who tried to get me not to leave my job. It was very discouraging to have so many conversations that were fear-based. I needed hope, I needed to be inspired, and I needed to be encouraged to think of solutions.

I would never, ever say that leaving my job was easy. It was probably the scariest thing I've ever done in my life. It was really scary, and there were so many fearful thoughts, and you helped me work through those. The thought that was the hardest to work through was, “who will I be without this job?”

I feel like I had become known for what I was doing, and the company was getting a lot of recognition for the culture. I kept thinking, “Who will I be if I'm not this person doing this thing?” And it took a long time for me to say, "I'm going to be a person who takes a chance on myself." I like to say I took a leap of trust, like, "I don't know what's going to happen, but I trust myself enough to know that this is wrong and I'm going to figure out what's right."

One other thing that was so important was that I took a month off. It was important for me to distance myself and think about what I wanted to do and remember who I am outside of my job. I took myself to the coast, I went and visited a good friend in Ojai, and I just dreamed about who I’d be on the other side of this. I know there are folks who can't take a month off, but take a week off. Take three days off. Take some time just to have that space. Go to your happy place. Go to some place that speaks to your soul - wherever you feel like you can rest, relax and think about the bigger picture.

Megan: Yeah, I remember when you came back from that month, that it was very clear. It was like, "No, it's over."

Emily: I mean, it was so clear that I gave notice the day I came back. There was no more hesitation. I mean, of course, it's hard. It's like a breakup. I had been there five years, and it was hard, but it was right. And ultimately, everybody understood that.

Megan: Now that you’re on the other side of leaving, what do your days look like, and (everyone’s big question) how do you pay your bills?

Emily: Well, I totally understand that people want to know this because I was so obsessed with this question when I was deciding to leave. I was so overwhelmed with fear about money. And because of this, I put pressure on myself to create all of these grand plans of the things that I would do after I left my job. I was like, "I'm going to start a company, and I have a business partner. And this is what we're going to do, and we're starting it now." There's nothing wrong with that, but I learned that I created all of those plans out of fear. It was just completely out of fear of not having money and believing that I needed to have something great that I was leaping toward.

The reality was that once I got to the other side of leaving - after my last day when I got to wake up in my bed and not have to go anywhere, do anything, or be anyone - I felt the freedom to actually not do anything for a little while. All of those grand plans I had made didn't have the same weight anymore.
I mentioned earlier that my health was not great. I like to joke that I slept for four months. For a good amount of time, and I believe it was about four months, I just rested. I enjoyed my summer. I took care of my health. I focused on eating healthy food. And I did some basic self-care that felt wildly overdue.

When I left, I was able to participate in the Self-Employment Assistance Program, which is a government-funded program for people starting their own businesses. That helped fund me while I started consulting.

And then I had a very unexpected thing happen - the love of my life, my sweet dog Coco, passed away. That just shook my world so hard. I feel like with any death, it causes you to think about what is really important to you, and I felt so strongly that I wanted to work with dogs. After her passing, I started fostering dogs, having a little home-based doggy daycare at my house and walking dogs in the neighborhood. I find that interesting because I remember being at the height of my stress during my job, and one of the things that I liked to do to calm myself down was to say, “I'm just going to leave my job and walk dogs.” It's so interesting that that actually happened in a way that I didn't expect.

Megan: And how have your thoughts and feelings about money shifted now that it's a more creative mix and not a steady paycheck?

Emily: I’ve definitely learned a lot about my relationship to money. That felt like such a hurdle, and I focused on it so much that it led me off track. But if I actually cared that much about money, I would have stayed at my job. Now, I care so much more about my time. I care so much more about my health, and about following that intuitive impulse wherever it leads me.

Over the past year, I started to ask myself different questions. I mean, we all need to make money, but to not just ask, “how will I make money?,” but “how can I help?” That’s been transformative for me and has been so important because I can give you 25 - 30 different ways of how to make money, but how I want to help is a shorter, more concise list. That's where I've been focusing: helping people, helping dogs and doing that in a way that decreases my stress and increases my health and well-being.

After I left my job, I also stopped spending so much money because the more stressed I am, the more I want to do something to de-stress. When I had a healthy paycheck and was stressed at my job, that manifested as wanting to de-stress by going to restaurants, going out with friends, going shopping, buying clothes and telling myself it was for work. My life is a lot simpler now. I don't need to go buy things because I feel pretty settled. I’m much more conscious of how I spend my money because I would much rather have my time.

Megan: I would love to hear what you would recommend to someone who is in that early stage where they’re getting that sense that things look good on paper, but it’s just not feeling right anymore. What would you recommend to someone in that spot?

Emily: First and foremost, I would suggest getting some support around ego versus intuition. I feel like that’s where people get very confused. The ego part of you can play a big role in deterring you from following through with what your soul wants or what your dreams are. In general, our society is very prone to lead with ego, and it’s where people can get confused and tripped up.

Where do you ultimately want to go? What are your dreams? A lot of the time we forget. It's important to remember who you are as a human and what your spirit is craving. Oh, and hire Megan as your career coach! I mean, truly, hire someone who doesn't think that you're crazy and irrational for wanting to leave your job. It’s rare to find that. I had family, best friends, even my own professional coach telling me not to do it, and that just frustrated me.

Do what you need to do to build the life that you want. I had to check myself on my own ego multiple times and focus on my qualities as a person versus my “successes,” my title, or my accomplishments. Honor what actually matters and honor your energy. I ask myself all the time, "What makes me tired, and what energizes me?" That's a really easy way to decipher who you want to be around and what you want to do.

Finally, just get support from people who believe in what's right for you and who also believe that you know what's right for you - because you do.

Thank you for sharing your story with us, Emily. If you’d like to connect with Emily or learn more about her, visit her website: emilylily.com.

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