Winning Even When You Lose

He wins even when he loses was the biggest compliment I received. Running for office is a privilege. It’s a chance to build a movement and to inspire your community. When I lost I remembered that. Most people do not get the chance to do it. I did. My family would remind me about all the support and donations and volunteers. People in the world are sick and hungry and why should I feel sorry for myself after an election. Live, learn and get back up. 

My first loss was probably the most fun I have ever had. The energy and the friendships all working together. We did not know much but we built on our childhood friendships through sports and neighborhoods and we did all we could. We were young kids from the neighborhoods of Cambridge.  I have lost elections by tiny margins and by 10 percent. I have also won them. Some wins come by small margins more with landslidesThe losses taught me more. Losing an election can either knock you off course or sharpen your sense of who you are and why you are doing the work in the first place. The difference is whether you let defeat define you or refine you. Tip Oneil wrote in his book “all politics is local” “ Anthony you got more votes than I did in my first run for council”.  That coming from the Speaker of the US congress gave me a lot of perspective. 

Public Defeat Has a Way of Stripping Things Down

When you lose privately, you can keep it to yourself. When you lose publicly, there is no hiding. People know. Some are kind. Some are awkward. Some disappear.

That exposure strips things down fast. You learn what mattered and what did not. You learn which relationships were real. You learn whether your motivation was rooted in service or validation. When you survive it you come out with a much better sense of who you really are. 

Keeping Perspective

After losing a very close state rep race at age 26, I was sitting outside the VFW hall afraid to enter to see my supporters. My little sister came out and with tears in her eyes said” there are hundreds of your supporters in there who are very proud of you. You did not lose, you won.” 

What is the Opportunity

After a loss you have to resist the temptation of feeling sorry for yourself. My campaigns were built on getting right back up and showing appreciation for your campaign team and supporters. Most importantly, supporting the candidate who beat you and recognizing their victory with class and sincereity.  You never know what tomorrow will bring , who will support you and what opportunity will arise. What is important is the spotlight is on to show what kind of person you are in defeat. 

After my hardest emotional losses  I had to ask hard questions. Why am I doing this? What am I actually trying to accomplish? Those questions are uncomfortable, but they are clarifying. Elections have a way of cutting through ego and getting to the core. However, I watched my mom never feel sorry for herself. Always got back up. Always said “start from where you are.”  and “Life’s not fair. : My father taught me to realize someone else is struggling way more than you are. Those two perspectives were like gasoline in my engine after political defeats or life’s setbacks.

Losing Sets The High Standards You Set When You Win

More importantly , when you win you have to remember the losses and realize your immense responsibility to help people and improve your community with the opportunity to serve. Those who win right away in my view, do not truly appreciate the office the same way. Public office is the opportunity to help your community. When I won I felt a deep sense of responsibility especially because of how hard we worked to get there.  

After a loss the next campaign starts the next day

When you win, it is easy to believe your own narrative. Losing involves starting over.

I never felt that there was a voter I could not ultimately win over. That is the confidence I have in people and my sincerity. The key was understanding that people decide on their own pace and you cannot force it on them. Sometimes it has nothing to do with you at all and everything to do with the moment. Never tell a voter they were wrong after an election. Prove who you are and that you deserve their vote with consistent actions. 

Politics should be personal and not gimmicky. 

Some of my clearest thinking came after losses, when I stopped talking and started listening. That listening shaped how I approached future campaigns and how I approached leadership even outside politics.The easiest approach is get up and work harder.  

Humility Is Not Optional After a Loss

Losing an election humbles you whether you like it or not. The question is what you do with that humility. You have to keep your supporters energized and together. If you can keep your team together, you live to fight another’s day. It’s an opportunity to demonstrate grace, class and resilience.

You can resist it and become defensive. Or you can accept it and grow.

Humility does not mean doubting your values or your ability. It means understanding that leadership is earned repeatedly, not granted once. It means recognizing that public trust is fragile and conditional.

The leaders who last are the ones who let humility widen their perspective instead of shrinking their confidence.

Titles do not define us 

One of the healthiest lessons I learned from losing elections and mistakes is that office is not identity. I remember after going through a very bad period an Ethiopian  woman running up to me and saying “ Anthony do you remember me? You helped my family so much”. She did not care about a mistake or setback. It made me realize that all the years of helping people is part of your legacy, It cannot be taken away from you. Your legacy is not created by social media posts and can’t be erased because of a  negative setback  

When you are in public office, it is easy to let the role consume you. You become the title. You become the position. When you lose, that identity disappears overnight.

It’s not the title or office that is your legacy at all. It’s the lives you have affected. People you have inspired and the quality of life you have made better for so many people. When you fall back on this kind of work. The work of helping people , not public accolades< it becomes a way of life long after you leave office. 

The politics of Helping people lives on beyond holding public office

Your best memories are helping a family secure housing, helping  struggling senior citizens get into a nursing home or senior housing. Mentoring a student who has lost their way and helping them get into college or start a meaningful career. These actions are your legacy. I was fortunate because when I lost elections for state office , I still had city council asc a platform to help people. However after I  left the state Senate I realized I did not need a title or public office to help people. They kept calling and I kept helping. I found a myriad of ways to help. My law office, coaching, non profits, charity work and just maintaining my network and will and intentionality. 

Winning is about Helping others

I have won many elections and had great titles and awards. What cannot be taken away is your investment in people. When a family sends a message that recounts an instance when you came to their aid, it is incredible. At the time you just help. Years of helping people becomes your real legacy. Investing in your community is tangible and it’s forever. When I have been down about a loss or setback someone has always called me for help. That inspires me to inspire them and remember that I am not done yet. Keep moving forward. Keep helping people. No time to waste.

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