I didn’t set a date to leave my corporate job.

I was waiting for a feeling—an internal knowing that would tell me, “It’s the right time to quit.”

I muscled through the work itself, feeling like none of it really mattered. While I wanted to leave, the fear of the unknown scared me.

Before I left, I didn’t have any clients—partially because I thought the only clients I could find were B2B SaaS clients and that wouldn’t fly with work.

While I had some clarity—I liked connecting people, traveling, and creating fun experiences—I didn’t know how that could make me money. I tried announcing a retreat only to cancel it a few months later because I didn’t get enough interest. I felt like a failure. On top of that, I was completely unmotivated at work, which made me feel more of a failure to my teammates who were counting on me.

It was… a lot.

In August, I decided to take a leave of absence to clear up some headspace and think about what to do. If you’re able to do this, paid or unpaid, I highly recommend it. It’s hard to think straight when you’re in an environment you’re trying to break out of.

During my leave of absence, I realized that while I was scared to leave, I was more scared of staying.

💵 Preparing financially

While I had a sense of how much money I was spending, I didn’t know what that was going toward. I signed up for Rocket Money and created a spreadsheet (which I still use monthly) to get visibility into my expenses each month.

This allowed me to get specific with my bare minimum number was. Because I didn’t want to sacrifice much with my current lifestyle, I knew that I needed to save at least 6 months of current living expenses to feel “safe”.

Questions to ask yourself:

• Do I know how much money I currently spend each month living my current lifestyle? Am I willing to change my current lifestyle during my transition?

• How many months of cash do I want to save up? Will I feel OK spending this?

🧠 Preparing mentally

Over the course of two years before I actually quit, I took on side projects that helped give me the confidence that I could earn some money on my own. While it wasn’t the salary I needed to survive, it helped prove to myself I am capable of figuring things out.

I also kept a few simple affirmations in mind when self-doubt would creep in:

• My career is a constant experiment. I can ALWAYS change my path.

• If I don't start, I'll never have the opportunity to succeed.

• I can trust myself.

Questions to ask yourself:

• Do I trust myself to figure things out?

• How does my body feel when I think about the thought of staying for another 6 months? How does my body feel when I think about leaving?

• What are some affirmations that will help me when self-doubt creeps in?

📱Preparing socially

Another big fear of mine was telling my friends and family I was leaving my job. The stories they had about my situation could easily influence me.

I selectively chose to speak about it more with some friends vs others. I chose not to tell my mom at first. Essentially, I protected myself a bit because I was in a vulnerable spot, stuck between thinking I should stay vs really wanting to leave.

Questions to ask yourself:

• Will telling my friends and family that I’m leaving help me or hurt me?

• Who will be supportive with my choice?

• Do I trust myself to be OK if negative or fearful opinions surface?

💭 Final thoughts

There’s no perfect time to leave your job. But if you have the financial runway and the mindset that you will figure it out, you might be more ready than you think.

The “feeling” I was waiting for never arrived in a dramatic moment. Instead, there was an internal knowing: This chapter has run its course.

💬 Your turn

How do you build self-trust when you’re about to do something scary?

✨ Weekly Feels

Happy Memorial Day! This weekend was all about recharging—I took long walks outside, did yoga, played volleyball, went to Othership, got a haircut, watched the Knicks game (!), and made some ice cream. It’s the simple things 🍦 

I’m off to Orlando for 9 days 😲 starting on Wednesday and then back to re-evaluate H2 of my business. Time flies!

🌟 Upcoming Events

I’d love to host some more events when I’m back in NYC! Ice cream social, anyone? 🙂 Stay tuned…

• June 9 - 18 | From Full-Time to Fractional: A Step-by-Step Launch Playbook for Senior Leaders | Learn positioning, pricing, and sales fundamentals to land your first client | Use code “FEELING FREE” for 15% off!

📖 Keep Reading

• What was the tipping point to leave corporate

• Managing other people’s opinions

• What I earned and learned in Q1 as a first-time solopreneur

💼 Ways to Work With Me

• Want to be featured in this newsletter? I’m looking for entrepreneurs who want to share their inspirational story! Simply reply back with interest.

• 1:1 Private Coaching: I’m offering free coaching strategy calls to those looking to build a more fulfilling life. Feel free to book some time with me!