Ego, Ease, and Expectation: A 3 part series

It’s important to understand your why and what you value. People will put their expectations of you, on you, and if you’re unclear on where you stand, you’ll accept theirs as your own.

Expectation: a strong belief that something will happen or be the case in the future.

Over the next few newsletters, I’ll be unpacking each of these words and the stories that shape them. This is important because in order to understand how I am designing my new systems and how I even got to the point of component failure, extra context is needed.

---

If you follow me on Instagram, then you may have seen me “soft launch” my return back to Google. Yes, after nearly 3 years away, I have made my return as a corporate girly from startup founder and the question I keep getting asked is “why?” 

Even during the hiring process, the woman interviewing me said, “You seem so much bigger than this place. Are you sure you want to come back? I feel you’ll tap out quickly.”

I want to start the story here because when starting over, the number one challenge I’ve come across is dealing with expectations. Expectations from myself. Expectations from others. 

Expectation

When I walked away from Google at the top of 2021 to start what became 7th Ave, I had no intention of coming back. It wasn’t due to reasons you may hear in the news like a terrible work environment or failure to receive proper compensation or denied rightfully earned promotions. In my 4 years at Google, I had a better than average experience - I always had amazing managers who were extremely invested in me, dope teams, was paid well, and enjoyed a good work life balance. I was seeking to leave because I felt my skills and impact could go further in building a solution for my community during the unprecedented times 2020 created than how I was being utilized at Google.

---

The transition from employee to owner came with an unexplainable feeling of joy and fear. We as a company had raised just under $4M, we had a bit of media buzz, and the future seemed promising. However, the trade-offs of my decision had completely changed my life overnight.

I had to be available 24/7, exchange the ability to be present for the sake of future-proofing the company, and give up on the idea of peaceful sleep due to going to bed every night with the fear I left too much incomplete to make any real progress the next day. 

People love to talk about the freedom and glitz of being an entrepreneur but I am here to tell you, it's ghetto AF! Now don’t get me wrong, it was by far one of the best decisions I ever made and I’m forever grateful for the woman I grew to be because of it. I found my voice, I learned how to take an idea and bring it into existence, and I met people who have forever changed my life.

And while those highs are phenomenal, those lows can take you to a place that makes you question parts of yourself you once were most confident in. This was a huge part of why I went on a 6 month journey to Europe. I needed space from unmet expectations and a chance to reconnect with myself.

When we decided to shut down 7th Ave in January of 2023, I was left in a place of not knowing what was to come next or where I would really land. I had unknowingly tied much of my self worth into the company, that once it was gone, very little seemed to remain of me. It was one of those situations of, ‘you gone cry in this Phantom or dat Nissan’? I chose the Phantom and took my butt to Europe. 

And boy did I cry… but crying on a beach in Malta definitely beat crying on my couch in Atlanta.

---

Europe brought me back to life. No one was looking for me, no one was expecting anything of me, and I honestly woke up each morning with no expectations of the day. I could just be. I wrote of how transformative that experience was for me in previous newsletters, but what it gave me most was the gift of perspective. 

I could properly grieve 7th Ave and the things that did and didn’t come from it. I could process the lessons learned and how to apply them to life, and in giving so much of myself to something that was no longer breathing, I had perspective on what really mattered to me.

In this journey of me returning to self, I found 3 hills I was willing to die on:

• Stability

• Advocacy

• Purpose

If the opportunity/relationship didn’t present these 3 things, it was and still is an immediate no. 

Stability:

I’m aware that the only thing constant in the world is change, but in the startup world, that cliche takes on a whole new meaning. After 3 years of it, plus an additional 6 months of nomading, I craved structure and the ability to sleep peacefully in my own bed. 

I desired not to be accessible, not to deprive myself of things in the name of extending runway, nor tie business metrics to things I use as creative outlets. I wanted to say “that’s above me” and genuinely mean it. I wanted to be able to take 3 days off and not feel I’m aiding in the end of my business.

Advocacy:

Advocacy is something relatively new for me. In 2021 a lot was happening with me personally and I checked out of every other part of life that wasn’t work. When I had a wake up call mid 2022, I didn’t recognize many of the spaces I occupied. 

That was the moment I realized the people you keep in life are by far the most important. There’s times life will cause you to check out and if you don’t have the right people around you to at least keep you afloat, you can spend years of your life working to recover from spaces you would’ve never put yourself in. 

So the questions I used to re-evaluate who got time and access to me centered around “If I were to check back out…”

1. Do I trust I have shared enough of me with you that you’d know what decisions I’d make?

2. Do I trust that you would actually make the right decision for me?

3. Do I trust that you’d advocate for me if I couldn’t do it myself or give me a voice in spaces I’m not present?

My circle got small, but life got easier. 

Purpose:

I realized that when all hell breaks loose, like it did in 2020, I never want to question if the work that I spent, and will come to spend much of my life doing, mattered at all. I want my efforts to mean something. To change something for the better. To be a catalyst for something or someone bigger. 

---

So, now that you have that context, when the interviewer asked if I was sure I wanted to come back, my answer was simply, yes. And for those of you who didn’t ask for the long story on my why, you got it anyway. 

Google was offering me exactly what I value currently in life. 

Stability: For me, Google has always been a place of stability. I interned there, joined full-time right out of college, walked away to start a business, and was welcomed back with open arms. I close my laptop each day knowing there’s a great chance I didn’t break the company and if I need to take a day off, I can without the guilt of not working or a bill going unpaid.

Advocacy: My now manager, prior to even meeting me and going solely off my reputation alone, essentially told the recruiter, “Give her what she wants, I want her.” Best believe I had some requests and just about each one was met. I told her when we finally did meet that the reason I took this job over a few other offers was because of her willingness to advocate for me prior to us even meeting. 

Purpose: I spend my days supporting nonprofits; more specifically, one that helps to find cures for childhood cancer :) I wake up each day rooted in the mission and it brings joy to my heart knowing my contributions can save a life.

---

If you’ve made it this far, shout out to you. So now you say, what does this have to do with managing expectations when starting over? I’ll say two things.

It’s important to understand your why and what you value. People will put their expectations of you, on you, and if you’re unclear on where you stand, you’ll accept theirs as your own. Take time to also acknowledge the paths you may follow can even go against your own expectations - and that’s okay too!

The interviewer had no ill intentions in her comments towards me. To be honest, I took it as a compliment. However, Given the chapter of life I’m in, I value certain things that entrepreneurship can’t give me at the moment. 

Expect a bruised ego. When starting over, the actuality of your situation versus your imagined expectations can vary greatly. That adjustment can take time and it doesn’t mean you did anything wrong, you are simply at the start of something new.

Most times your plan is well beneath the one God has in store. So in reality, you needed a bit of redirection anyway :)

With love always,

Jamie ✈️ 🌎