A New Year and Big Career Transitions

January marks a year since I took the plunge to build The Grand full time.

Entrepreneur origin stories are often glamorized, dozens of podcasts and articles make it seem like one day an aspiring founder just wakes up with a brilliant idea, decides to quit their corporate job, and then starts a company the next day. My personal experience transitioning from First Round to The Grand was full of anxiety and question marks. It took me about 6 months to make the decision, and then another 6 months to make the transition.

Making the decision to leave a job I loved to pursue a high-risk idea was the hardest part of the process. Running Dorm Room Fund at First Round was, by all means, the best job I’d ever had. I got to work on a mission I deeply believed in with a brilliant team I respected immensely. I had autonomy, creativity, ownership, flexibility. I was compensated well and had unlimited vacation days. But after 3 years of leading Dorm Room Fund, I could feel my learning starting to plateau and my mind starting to think about new problems to solve. I told my parents, and I remember my mom distinctly saying, “Why would you throw away a golden bowl to go hungry?” She was right pragmatically. I’d spent a decade working hard to secure a job like this, and quitting would mean changing my life dramatically. And plus, my mom added, as a thirty-year-old woman, I really should be focused on starting a family, not making a big career change.

I tried to put these thoughts aside and focus on building new products and finding creative ways to grow the fund. But months later they were still prescient, and I couldn’t ignore them anymore. I started telling a few colleagues and friends, and from those conversations realized I wasn’t alone. Many of them shared similar ambitions to pursue new ventures, and similar fears in making a high-risk career change. I felt comforted and supported knowing I had a group of peers to lean on.

Finding confidants and a supportive community gave me newfound confidence, and ultimately helped me take the plunge. This is why Anita and I are so excited to be launching The Grand Quest. Career transitions can often feel lonely and ambiguous. The Grand Quest is designed to combat that and support you through this major change.

Learn more about The Grand Quest on Making Big Career Transitions.

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Upcoming Sessions

Co-Parenting: How To Be Equal Partners in Parenthood 1/9 - How do couples navigate co-parenting and share roles and responsibilities? If you're a current parent, or planning to be a parent one day, join us for a session with Grand Guide Michael Lander who will share his experience in two different co-parenting dynamics and the rewards and challenges of fully sharing parenting responsibilities.

Here’s to a bold and beautiful new year!