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Bold leadership strategies

  • Feb 20
  • 3 min read

By Paige Arnof-Fenn


My first job out of college was in finance on Wall Street in the 80s. I realized early on it was not a good fit so I wanted to switch career tracks. Being a Financial Analyst in investment banking paid well but the hours/lifestyle didn’t leave time for anything else and I really did not enjoy the work even though I was always good with numbers/strong analytically. I made a 2-year commitment to the firm but knew I wanted to work in a career after that was a better balance between my left and right brain. It was a bold decision to leave a high paying finance job but a friend at the bank helped me realize my skills/strengths could be put to better use.


I really disliked my job and knew I wanted to do something else but had no idea what that would be, all I had ever wanted to do was finance/banking so I was stuck. She prodded and said there HAD to be parts of my job over the past 2 years I had enjoyed and finally I said yes there were in fact 3 things I liked about it, running ads in the WSJ & NYT when deals closed, planning the closing dinners to celebrate the end of a successful transaction & choosing the “deal toys” to commemorate the event. She blurted out “Paige I have no idea why you always thought you were a finance person, every single thing you liked about the job is marketing NOT finance! You liked advertising, event planning & promotions. You are a marketing person! That is what you should be doing!” She was right. I got the top grade in my first year required marketing course for my MBA and a great summer internship that led to a full time offer in marketing post-graduation. I’ve never looked back. I am forever grateful to her for setting me on such a fulfilling career path. I have no idea how long it would have taken me to figure it out without her brilliant insight when we were 23. She saw my authentic strengths which saved me a lot of career angst for sure!


Being bold as an entrepreneur means showing up every day with renewed energy and enthusiasm to find new customers and continue to delight the ones you already have with your smarts, humor and attitude. It takes persistence, humility and guts to show up every day with a smile, strategy and a plan so I think entrepreneurs are bold by definition. It means making decisions with uncertainty and knowing you can course correct as you go and learn more about your customers. Bold is a way of life for entrepreneurs. It is not about being risky it is about being brave, confident and smart. It takes courage to trust your gut and face your fear so you can find the right path and lead with authority. The best leaders live it on the inside which is the most effective way to show it on the outside.


It is possible to rebrand yourself if you are strategic about the process. It is important to have a story to explain your transition and show confidence in your decision not to be defensive about it. Since leaving finance I have loved the work and have been in marketing ever since, first going in house at large Fortune 500 firms like Procter & Gamble and Coca-Cola then running marketing at 3 startups and now as an entrepreneur. I would tell someone who is nervous about making a career change that if you are not excited by your job, I am a big fan of finding transferable skills and ways to bridge to another track to find something you truly enjoy spending time doing that shares your talents and gifts. Good people tend to travel together personally and professionally so finding smart and generous people early on who can connect you to other like-minded people who give more than take and share their wisdom always leads to great opportunities and adventures in my experience.


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