No Regrets: Living a Life Looking Forward

And not letting the past anchor you

Regret is the act of looking backward, rehashing what could have been instead of embracing what is and what could be. The more steps you take while looking back, the fewer steps you take while looking forward to where you could go. 

I decided when I had kids that I would live without regret. So much of parenting, especially motherhood, seemed to be about guilt, and I didn’t want to spend my time with my kids that way.  Each time I failed, rather than spend time feeling guilty or bad, I resolved to instead look forward and make changes from there. I then started applying this philosophy to my career and work. Rather than obsess over what I didn’t say at a meeting or an opportunity that I missed, I now think about how to better take on the next challenge. This doesn’t mean that you should not learn from the past, but you should never let it anchor you.  

Seeing the world as the “future you” 

What does your future self wish you had done today? 

We often see our careers in steps. When we are in a role, the next step is the next promotion, or perhaps the chance to manage. Then it is becoming a manager of managers, or maybe a director. After that it is about increasing scope, maybe becoming a general manager or a vice president. But rather than looking one or two steps ahead, you should start from the future you want to achieve and then look back to where you are today.  

When we make decisions as a leadership team, I often ask the question, “What do the future versions of us, five years from now, wish we had chosen to do today?” It is too easy to get caught up in local optimization or the easy thing that is immediately ahead without exploring the bigger bets and step functions that we could be working toward.  

Learning from failure 

Nothing is a true failure if you use it as a stepping stone to future growth. 

I once took a job offer without negotiating and regretted it, so I decided never to do that again. Instead of thinking about how much money I lost, I decided that I was going to be smarter next time.  

My failure to negotiate taught me so much that I have even started paying it forward. For example, once a woman was given an offer to join our team. I knew she would likely not negotiate, so I pushed for the highest offer we could give, negotiating on her behalf with our internal team. They didn’t love this, since they wanted to leave some room for her to ask for more, but I told them that she likely would not do so. She got the offer and, as I expected, she accepted without negotiating. When she started, I told her what I had done, and I begged her never to do that again because next time it was likely no one would be on the other side looking out for her. 

On a different occasion, a friend asked me for advice about an offer she had received. I saw it and immediately knew she was being lowballed. I gave her a negotiating strategy and explained how to get what she wanted by leveraging a different offer and getting both sides to counter. She ended up with multiple times the stock she had been offered at the start. 

I treat my costly experience in not negotiating as a lesson that I can pay forward to women throughout the industry. My failure has been a catalyst for me to teach others to not make the same mistake.  

Making continuous improvements 

Regret often centers around what we didn’t do. It tends to come as a result of missing some goal or not achieving something we wanted for ourselves. For example, a New Year’s Resolution may be something like “go to the gym every day” or “get promoted,” but studies show that within three months, 90 percent of gym-goers will drop out (ref), and getting promoted is often not totally within our control. 

When we fail at a goal like this, we are often disappointed and demotivated. 

What if, rather than focusing on fixed goals, we looked for continuous improvements?