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? If your goal is to write 1,000 words per day, that is great, but once you miss a day, you start feeling like you are falling behind until you eventually give up. On the other hand, if your goal is to write and publish more, without setting a hard and fast number, then it’s easier to make incremental improvements and see gradual progress. If you fail to check off a day, you can more easily catch up the next day. Better to have written 1,000 words over two days than to write 0 words one day and then feel like 2,000 is too much of a gap to close. Seeing life as a road toward progress rather than a fixed destination reduces regret. 

Follow the One Percent Rule 

So much of success is being open to learning and growing. I grew up extremely shy, to the point where I barely spoke up in class. When I got to business school I realized I had to speak up or risk my grade which had a large class participation component. Ever the good student, I knew I needed a different set of tactics, so I taught myself to speak in front of others. At first, it was about quantity; I created a fixed list of comments I needed to make in class every week, and in the corner of each of my notebooks, I marked how many times I spoke up. I then started rating the quality of my comments as I made them. Eventually, I grew comfortable enough to actively debate with other students in class. 

For the past seven years, I have returned to the Stanford Graduate School of Business to speak on an annual alumni panel in front of over a hundred students. I sometimes share the story of how shy I was, and many people in the audience seem surprised. Sometimes when I look back, I am too, because I see how far I've come.

If you are growing every day, there is no room for regret, only forward progress. I like to quote the philosophy of one percent: “If you improve by one percent every day, in a year, you will be 37 times better.” That is something that looking back will never give you.  

Reframe, reframe, reframe 

Something bad happens. You make a mistake at work. You say the wrong thing or you don’t speak up. It’s easy to spin out and beat yourself up, but the more constructive response is to use that negative experience as the trigger for positive change.

I was speaking to a woman the other day who asked for advice. She was stuck in her head, replaying something unfair that had occurred, and was unable to move forward. But it was something that could have happened to anyone, and she took entirely too much blame on herself for something she didn't have control over.  

Often regret is the failure to reframe. In her mind, she felt regret and even guilt over what had happened. I tried to help her reframe the situation as one where she was the victim of an unusual circumstance and that she could and would find success from here. 

I was once passed over for a job that I really wanted. I knew that I could either let that experience crush me or use it as an impetus to prove my worth. The next year, I did my best work ever. I chose to not allow that failure to be something I dwelled on, and instead used it as a catalyst for growth.  

How we choose to look at the past can either be what frees us or what holds us back.  

Living without regrets is freeing. Rather than spending your time looking back, you can spend your time moving forward. Rather than obsessing about what could have been, you can take that energy and create what you want for the future. Rather than allowing something negative to define you, you can choose to reframe it into a springboard to achieve your dreams.