Mentoring Heartbreak

This past couple of weeks have been difficult, a roller coaster set of emotions. I knew since the beginning that mentoring was not going to be easy. For me, it is not a business or a chore. It is a purpose. I’ve experienced the heartbreak that accompanies closing your business (no matter the reason) and the thrill of success.

I know the pains and the gains of being an entrepreneur; that is why I’m a mentor. However, this pandemic has brought a different side of mentoring. More sensitive conversations rise as mentees trust you with details about their challenges and feelings of despair.

The HeartMath Experience

This Monday was different; there were more personal stories than ever. After several mentoring sessions, I closed my door and cried my soul out, my heart aching in frustration and sadness. I listened to small business owners with traditional brick and mortars, part-time workers, furloughed teachers, and senior executives who recently lost their job, all of them asking for help on how to start an online business.

My duty as a mentor is to guide them and teach them to navigate entrepreneurship, the ups and downs, and everything in between focused on protecting their assets and liabilities.

I had to reach out to my colleagues, my senior mentors who have decades of experience ahead of me, seeking guidance. How to keep objectivity when your mentee crumbles in front of you? What words can you say to make them stop investing money they don’t have? How can I express to stop falling for that clickbait at 2:00 am? When their eyes are exhausted from spending hours editing their resume on LinkedIn praying that this time, hopefully, they will get that interview.

One of my colleagues told me that there are two schools of thought in business mentoring, the first one, the encouraging positive mentality. Some sort of a maverick spirit, inspiring the entrepreneur or small business owner to keep on, pivoting as many times as necessary until they eventually succeed, or in the end, they figure out it was not the kind of business they wanted.

The second type of mentoring, the realists or the blunt ones (like me). A foot on the ground, goal-oriented kind, seeking to bring light into planning, milestones, and feasibility. We tend to ask how much they are willing to invest, in time and money, continually asking about hidden costs and expenses, not only sales. Perhaps the hardest thing we ask our mentees is to go out and sell the product. If they can sell at least ten products, then they are on the right path. If not, they need to reconsider what they are getting into before investing more.

Who is wrong, or who is right? I’ve spent a reasonable amount of time balancing both approaches, inspiring my mentees to dream and shoot for the stars while keeping one foot on the ground.


There is a thin line between following your dreams and working on your dreams. Both born from desire, passion, and will to have something of your own and control how and where to work.

The difference is that the first comes from excitement and motivation. The later derives from planning, goal setting, and clarity.

Having both its a balancing act every entrepreneur has to learn.

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