Interested in starting your own entrepreneurial journey in personal development but unsure what to expect? Then read up on our interview with Rachel Lipton, Founder, and CEO of Rachel Lipton Coaching, located in San Leandro, CA, USA.

What's your business, and who are your customers?

With a decade of experience elevating organizational strategies and leadership development programs, I partner with mission-driven leaders and teams to lead effectively from a place of confidence and strength in service of happy, high-performing workplaces. I support teams to see what is happening at the systems level (including staff, board, beneficiaries, donors/investors, and the larger community) and how they can address challenges collectively for greater retention, engagement, and impact.

Tell us about yourself

I participated in a coaching program in 2014 and found it very supportive at a time when I was working in a toxic workplace. I was doing a lot of evaluations of leadership development programs as a consultant, but I realized I really wanted to be facilitating growth and change in leaders rather than evaluating it. In 2018, I started my own professional development journey to becoming a coach, became certified, and have never stopped learning! I started coaching full-time last year, and it was the best decision I've ever made. As a millennial who graduated college at the start of the 2008 economic crisis, survived multiple toxic work relationships and cultures and had to rebuild my life in the midst of the COVID pandemic, I am passionate about helping leaders feel passion and energy in their work and creating relationship-focused teams. Workplaces don't need to be toxic. But we have a lot of work to do to make them better.

What's your biggest accomplishment as a business owner?

I am someone who gets right into action when I have an idea. My biggest accomplishment is not getting in my way and just trying things. It's fun to have the freedom to throw spaghetti on the wall, so to speak, and see what sticks. I love being creative and in service of amazing people I work with doing good in the world.

What's one of the hardest things that come with being a business owner?

There are a lot of ups and downs. You have to be able to adapt and learn quickly, and sometimes the hardest part is the inner narratives that pop up. Being an entrepreneur takes a lot of inner work, and you need your own support system to show up with the energy you want to bring to your business every day.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. Get your support people together! Work with a coach or mentor (or both!). Gather a posse of other entrepreneurs building their businesses.
  2. Always know your "why" behind what you do. That's your compass point for yourself and your message to others.
  3. Have a financial cushion for at least one year, if not two. No one is wildly successful overnight!

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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