5 Big Regrets That Leaders Have to Overcome to Fulfill Their Dreams

By Marissa LevinFounder and CEO, Successful Culture

The road to success is filled with setbacks. Pain is inevitable, but suffering is optional. Here are steps to moving beyond regret.

Building a business can suck the life out of you if you're not careful. Entrepreneurs don't have an off-switch, which means they constantly think about how to push their business further. They also put themselves through the ringer about why they aren't doing "more."

As I've built three businesses

over almost 25 years, I've learned firsthand the power of mindset, and the importance of practicing self-love, self-forgiveness, and self-appreciation.

Recently I attended the funeral of an extraordinary businessman who passed away from cancer. Over 50 years, he and his brother built up a business from nothing to an enterprise worth almost $1 billion. But as the eulogies about him made clear, his legacy of love was just as strong as his legacy of leadership.  

This inspired me to reach out to entrepreneurs to learn about their biggest regrets on their journeys, and how they made peace with them, so when they look back at the ends of their lives, they aren't burdened with any sense of regret. 

1. Not spending more time with family and friends.

Many leaders regret the disproportionate number of hours they invest in their business, compared to the time they invest in their relationships.

To overcome this, they've instituted strong self-discipline and structure to be ruthlessly focused. In my work with CEOs, we constantly revisit their priorities to ensure non-essential to-do tasks don't creep into their schedules. 

2. Not prioritizing health. 

Health problems have a way of creeping up on us. According to a Harvard Business Review study, workaholics have an alarming likelihood of having a heart attack by the age of 50. 

There are many ways to address this:

• Commit to scheduling all required doctor's appointments, and keep them. 
• Analyze your work patterns and change them. Put buffers in place to disconnect. 
• Take up an activity that keeps you physically active. Commit to a regularly scheduled class at your gym, or join a sports team. The commitments will force you to work your schedule around the commitment and to show up. 
• Evaluate how much of your identity is wrapped up in your work. If nothing else defines you, consider how you can branch out to develop more emotional connection and fulfillment. 

3. Not remaining true to values and what matters.

As businesses grow, it's easy to go down the slippery slope of only chasing revenue. Especially in times of financial difficulty, it's tempting to chase low-hanging fruit that doesn't align with your organizational goals. When leaders feel their sense of purpose becoming blurry, they say they suffer both personally and professionally. 

The brother of the businessman who recently passed away said he and his brother always remembered where they came from and who they were, and that their core values and purpose in their business remained constant over 50 years. 

4. Holding on to failure, lost dreams, and what could have been.

Entrepreneurs love to hold onto broken dreams. "What if I would have moved faster?"  "What if I would have moved slower?"  "What if I would have risked more?"  "What if I would have risked less?"

Being able to release what is no longer viable is one of the most important strategies for accepting what is. One of my favorite quotes about letting go is from from Darren Endo, chief creative cfficer of Zivelo: "Time gives us the best perspective, and most things will make sense later on, if they even still matter to us at all."

5. Holding on to everything and not delegating.

One of the most common regrets from entrepreneurs at companies of all sizes is not building teams or not trusting teams fast enough. We can't do everything well. In my work with my CEOs, I relentlessly remind them to focus on work they love, that they do well, and is their best use of time. Everything else should be outsourced.

Regrets come in all forms and impact everyone differently. Ultimately, they tell us our best laid plans often don't come to fruition, But that doesn't mean we have failed. It simply means that thing have turned out differently than intended. The good news is that at every moment in our lives, we can choose to change our path.