Meet Bob Wheeler

We caught up with the brilliant and insightful Bob Wheeler a few weeks ago and have shared our conversation below.

Bob, first a big thank you for taking the time to share your thoughts and insights with us today. I’m sure many of our readers will benefit from your wisdom, and one of the areas where we think your insight might be most helpful is related to imposter syndrome. Imposter syndrome is holding so many people back from reaching their true and highest potential and so we’d love to hear about your journey and how you overcame imposter syndrome.
For years I felt i was just really lucky. I’d land on my feet and things would work out but I knew it was just luck. I wasn’t the smartest. I didn’t think I wasn’t the quickest. I was just lucky that I put in lots of effort and was lucky that things worked out with clients. And luckily, I was able to think on my feet. I spent a lot of time waiting for things to fail, waiting for people to find out I was a fraud, waiting for people to see that all of the work I did had no substance. I was in a state of constant fear. When I started my own tax practice, after the first year, I assumed no one would return. And then they did. Plus a few more. Then the next tax season, i assumed no one would return. And they did. Plus a few more. Within about three years, i was already up to over one hundred clients. And every year I assumed no one would return. It took about seven years before I started to trust that people would come back. One of my clients asked me to meet with his financial advisor. I did. We hit it off and the advisor started referring clients and giving my name to other advisors. Because of that one meeting, my client base jumped to almost three hundred clients and then five hundred clients within a short time. A couple of the advisors told me that they wished they had half the loyalty from their clients that I had from mine. I started hearing over and over that my clients were very happy with my services. My clients were referring others to me. Financial advisors started referring new clients to me. At about the five hundred client mark, I realized that maybe it wasn’t just luck. I was actually connecting with my clients and helping them in an area that many feel uncomfortable. I wasn’t just lucky. I had a solid education. I truly wanted to be of service to my clients. I did actually care about my clients. And when I didn’t know the answers or how to do something, I asked and I learned. I started setting boundaries about the types of clients I would take on. I raised my fees. I learned to say no to clients that didn’t feel like a fit. I finally began to trust myself; the value that I brought to my clients, the positive atmosphere that I created for my team, and the reputation that grew from the work that we did and the client reviews. If someone had told me twenty years ago how things would have turned out for me, I would have never believed it. And here we are.

Great, so let’s take a few minutes and cover your story. What should folks know about you and what you do?
When I started my tax practice, many of my clients were in the entertainment industry because in addition to being a CPA, I was doing stand-up comedy, improv comedy and some acting. The tax prep stuff was going to be my side hustle. When I started working with folks as their CPA, they weren’t following what seemed like practical advice. I realized quickly that if I didn’t understand where people were coming from emotionally (unconscious sabotage, limiting money beliefs, etc), I couldn’t help them. So I started to focus on the emotions around money and finance as part of my mission. I started looking at my own limiting beliefs around money. People seemed to resonate with the probing questions I asked. I started sharing my own fears and emotions around money. I started sharing where I fell short and made mistakes. Becoming emotionally invested with my clients helped me to see that I was building a business of relationships, not just tax client returns. So many people started sharing their fears and their stories. I realized my mission was to help normalize conversations around money and to let people know that they are not alone in their financial fears. Many of us never got the financial literacy that we needed and there’s no shame in not knowing what you don’t know. So I talk with my clients, lead workshops, host a podcast about money and emotions and I speak with groups of people about their relationship with money. We all deserve to have a healthy relationship with money and I’m excited to help people discover and change their money stories.

Looking back, what do you think were the three qualities, skills, or areas of knowledge that were most impactful in your journey? What advice do you have for folks who are early in their journey in terms of how they can best develop or improve on these?
Leading from empathy and gratitude as well as knowing that I don’t know are three things that feel most impactful. For me, it’s so important to get really curious about ourselves, to find things really interesting. This takes it out of judgement and makes space for us to be more compassionate with ourselves. “Isn’t it interesting that I often overdraw my bank account. Isn’t it interesting that I love to go on shopping sprees. Isn’t it interesting that don’t believe I can have abundance.” Somewhere along the way, I picked up the student mentality, not the expert mentality. If I’m an expert, I already know everything, and things get missed. If I’m a student, I’m much more open to learning new things because there is so much to be learned. When I work with folks, regardless of where they are in the journey, I usually ask about the cost/benefit analysis of their situation. What are the payoffs/benefits for staying small, not taking risks or not moving out of their current situation or story? The answer might be that they don’t have to fail or disappoint people. I ask about the cost of their current situation. That answer might be the cost is that they have given up their dreams, lost their passion or disconnected from family members. The more self-compassion and safe spaces we can give ourselves, the more we can experience healing and connection. Trust yourself as you move forward, even if you move forward with fear. The payoff is huge.

Who has been most helpful in helping you overcome challenges or build and develop the essential skills, qualities or knowledge you needed to be successful?
There was a point in my life that I was still doubting myself and doubting that I had any impact and I wasn’t sure if I had a purpose. I wasn’t even sure if I still wanted to even be alive. Things felt hopeless on the inside even though on the outside things seemed pretty amazing. I was referred to Ann Bradney and a process called Radical Aliveness, a somatic/leadership training. I set up an initial meeting/session. I was told that I could have all of these amazing things in my life, authentic relationships, community, connection, impact, purpose. It sounded amazing and it sounded impossible. I walked away and didn’t look back for a year. Things internally got worse, and I realized that I either needed to step up or I was going to find a way to step out. I decided to join a group. I started doing mini-workshops. I was in complete terror but found that I was in a safe place to being the healing process. I learned to work through my fears. I learned to embrace the terror that had been with me most of my life. I learned to stop presenting the best version of myself and replace it with a more authentic version of myself. I went through a four year personal transformation program as well as somatic therapist certification. I learned to trust myself. I learned how to embrace my leadership and to give sound to my voice. I started taking risks and letting people see the real me. It not only saved my life but it gave me the foundational skills to move forward. I gave myself permission to thrive and it reminded me of my purpose to be of service.

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