What is the riskiest decision I have ever made during my career and why?  During a recent interview for an MBA Capstone project on risk management during my career, this was my very first question from the students. In my experience, the riskiest decisions often have both professional and personal impact. This interview led to some great discussion, so I decided to share what I’ve learned about managing personal and professional risk throughout my career.

In over 25 years of holding different roles with different companies, my latest move to the East Coast as Chief Human Resource Officer was the riskiest. It was not because of the company and the work, it was because of the profound impact on life and family. The problem with considering a big move is that when you take a house hunting trip, it feels more like a vacation than a permanent, life-altering move. It was not until we were packing and leaving that it hit all of us on what was happening.

I was faced with the reality that I was moving a junior in highschool and an 8th grader. On top of new schools and friends, the little everyday setbacks were different on the East Coast. Through a very difficult 4 years we are all surviving, and in some ways, even thriving. Recently my child who struggled the most with our move shared that this was in the end the right thing for our family. My kids got their dad back and we have more opportunities to connect as a family.

During this same interview some of the other questions on risk from the interview were thought-provoking. The students asked about my least-risky decision in my career—I responded, “taking an easy role that was not challenging.” Decisions like these have very little risk, and very little reward.

They asked about advice for risk management to someone new in their career. My advice is to take a balanced approach. Really evaluate the “why” behind every decision you make. Also, get diverse perspectives on the decision and look at the risk from a 360 degree lens.

We discussed risk management in the future. From a business side, data and machine learning will always be evaluating all risk situations and will build models to educate. From a personal side, it will be very individual and I hope we never become worried about risk. Because you would never see the reward that comes from all those opportunities.

How did I build strengths in my career and what did I do to compensate for weakness? Simply never stop learning, reflecting, seeking feedback, learning to be ok with failure, understand who you are through self reflection and awareness and make sure you have a balanced team.

Change happens in all aspects of life, so when evaluating risk in personal and career decisions, believe in yourself and have faith. Learn to be comfortable with uncertainty. “Trust” that you have done your research, took good partners and have done your very best.

How do you build relationships and what are the advantages of the network you have when it comes to risk? I am a connector and driven to learn. So I will accept and meet anyone from anywhere to learn. Seek partnerships and friends from completely different backgrounds. I love the diversity of thought. Because of the network, I am confident through all of their feedback that I will make the best educated decision. Both professionally and personally. 

How do people manage risk during tough economic times? I believe the smart ones focus on shutting out the noise and focus on their strengths and what they can control. Have faith that if you follow the principals and learnings from before, you will get to a good spot. 

Can I think of a time when my passion led me to make a correct or incorrect decision? I ended where I began. This move. I have thrived and my family is thriving like never before. I can say that I am part of something special that is transforming lives like I never thought possible. I can say at the end of each day that we made a positive impact.

I share this with you for the simple reason that I began this blog. Life is hard and we have a responsibility to share our learnings both good and bad with those around us. No facade here or needing to conform to what society expects.

Start and end your day with love and a commitment to make a positive impact on someone or something. Together we can change the world.

Be Well,



  • Mindful Bob


    A ‘culture catalyst,’ I thrive when impacting the world around me. My expertise includes change management, cultural change initiatives, recruitment and retention strategy, organization design and organizational effectiveness, and total rewards. My professional life drives a focus on “ Employer-of-Choice culture at Ocean State Job Lot,”  “In recent years, we have made a concerted effort to transform our corporate culture to a more healthy, balanced and engaging place to work. We have achieved that, resulting in an increased rate of retention and greater diversity among associates.” Our efforts have helped  earn OSJL recognition in America's Best Midsize Employers, Forbes (2017, 2018 & 2020); Top 1000 Companies Worldwide for Millennial Women, Mogul (2018); Healthiest Employers, Providence Business News for 5 straight years; Worksite Health Award - Exemplary, Greater Providence Chamber of Commerce and Blue Cross and Blue Shield of RI (2017, 2018), 2019 and 2020), and more. As a believer in collaboration and giving back, I am a presenter and collaborator for CHRO Online, the HR Leadership Council, and the Northeast Human Resource Association. I'm also a consultant and advisor for several startups. As a speaker and published writer on culture change, transformational leadership, and organizational effectiveness in the new world. Simply put, we need to lead with LOVE. You can follow my work on bobsellethehrguy.com.