Last week, I talked to two friends, Lee Ramsay and Jess Lee, who left their corporate careers to pursue entrepreneurship. Lee started her events company and Jess started and sold Daily Work Journal and most recently, Surfers Jewelry.

While there were many questions submitted, I wanted to go deeper into the question:

What was the tipping point(s) for you to leave corporate and pursue entrepreneurship?

🎥 If you missed the event, you can check out the recording here.

Why Lee left her 10 year consulting career

Lee thought she would just be at Accenture for a couple of years but multiple promotions later, she found herself still there 10 years later.

In the pandemic, the job got even more stressful.

It wasn’t until she woke up one morning and looked in the mirror and noticed that all of her hair turned gray.

She decided to take a leave of absence and just figure things out. When her friend was tired of planning a delayed COVID wedding for the third time, Lee offered to plan it for free.

She went back to Accenture for a few months to get her finances in order, quit, and started her business.

How Jess prepared to leave corporate

Jess started in Consulting but immediately knew it wasn’t right for her.

When she transitioned into Data Analytics, the reasons were similar—it paid well, and it was what her friends were doing—but she realized that she didn’t want to be a VP of Data one day.

That’s when she started looking for what else she could do and discovered Executive Coaching.

Different than Lee, she bought herself time to train as a coach while gaining income from her data career.

When the pandemic hit and “the world was ending”, it gave her the push she needed to make the leap.

With her latest venture, Surfers Jewelry, she tells aspiring entrepreneurs to keep their hearts open to what you can see.

My tipping point

When I was in my 9-5, there was a voice that told me, “Is this really what you want to be doing for the rest of your life?”

I regretted not taking action during the pandemic, and I selfishly wished there had been another major event, like a layoff, that would force me to do something. At the time, I lacked the guts to do anything about it myself.

Even though the voice inside of me was telling me that this wasn’t it, I waited years for my tipping point—a tough conversation with a manager that made me feel undervalued—to finally make a change.

💬 Your turn

Did you have a tipping point? If you’re unhappy with your career, are you waiting for something to push you forward or are you starting to make a change now?

✨ Weekly Feels ✨

Feeling sunny 🌻: I definitely did not know it was Daylight Savings Time this weekend so when I woke up at 11am on Sunday, I thought my body really needed the sleep. Now that it’s here, I’m excited for more sunshine and being outside!

Feeling sweet 🍨: Sometimes you walk into shops where the people working behind the counter are so happy to talk to you. Randomly went to Alphabet Scoops this weekend and had just that. Check it out if you want a great value and a fun conversation.

🌟 Upcoming Events 🌟

Why generalists are built for portfolio careers - Anna Mackenzie | Tuesday March 25 (Virtual)
I’ve subscribed to Anna’s substack as I’m building out my portfolio career and wanted to share this event if it’s helpful for you too!

Wine & Wealth: Multi-Passionate Meetup | Wednesday, March 26 (NYC)
​I’m hosting a casual meetup to bring together multi-passionate individuals for a conversation about how to create financially lucrative career paths that don’t fit into a single box. RSVP with the link above!

📖 Keep Reading

• What if you didn’t have to choose one thing?

• Money (used to) rule everything around me

• At least I’m flying free

💼 Ways to Work With Me

• 1:1 Private Coaching: I’m offering free coaching strategy calls to those interested in career and lifestyle coaching with me. Feel free to book some time with me!