Lessons from the Idealist’s Journey


I have recently embarked on my third year serving with a fantastic organization that has been steadily gaining traction over the past 22 years: City Year. I think back to 2 years ago with an ever-impending deadline approaching (college graduation) and not having the most clear idea regarding what I wanted to do with my life (not many people do at age 22.) I remembered that I had some friends who had completed their own City Years and how much I respected them, people who had given up (at least) 1 year of their lives to serve a cause greater than them so that they could help bridge the achievement gap and, by extension, give back to an underserved community.

When I submitted my application I had no doubt in my mind that I would be accepted. No doubt was necessary because just one month later I was signing a confirmation letter to join the 2009-2010 City Year San Jose/Silicon Valley Corps (pronounced “core”). While gearing up for my year of service I received a call from the site’s then Recruitment Director to ask if I would consider joining their ranks 1 month early to help launch a new initiative. There was no question-I was there!

Walking into the City Year offices 2 years ago, I can still recall the feeling of belonging I felt almost instantly. I knew that this was the place I wanted to be for a long time. I knew that this would be my career: serving those who had been left behind by the ‘system’. After that first year my feelings did not wane. In fact they grew stronger. I applied to, and later was offered, a position to be Team Leader for the 2010-2011 year. Leading a team of 8 of my peers was at once one of the most challenging and rewarding experiences I have ever had. It pushed me to be a better leader, learner, and doer. With 2 years under my belt, there was no stopping. In July I started my 3rd ‘tour of duty,’ signing up to continue being on the front lines of fighting the issue of educational inequality.

The past 2 years have been fraught with lessons that I will continue to use as I work to serve students and strengthen my belief in the power of young people. Here are the top 5 lessons I’ve learned that have kept me performing at my peak and wanting to be a better servant leader.

1. Stay in your lane

Many of us characterize ourselves as over-achievers, always jumping at the newest leadership opportunity, striving to show your worth to everyone that matters. This isn’t a bad thing but learn to do these things gracefully. Almost any job that you do or role you assume does not happen by itself. I have learned to work on a team even when it feels like I’m a team of one. Learn the strengths of those around you and capitalize on those. Learn where you fit in within your organization/company and execute accordingly. If you recognize inefficiency in the system, communicate it professionally and to the people whose role it is to hear those concerns. Don’t skip your leader.

2. Invest in your strengths

Becoming a better person requires learning what you’re good at and focusing on those skills. We live in a world that tells us that, in order to be considered a ‘good’ leader, we must become ‘good’ at everything we do. Not only is this not possible, it’s not sustainable and it holds you at the level of ‘good’. My 2 years of working at City Year have taught me to push myself from being ‘good’ to ‘great’ by learning what my strengths are and to constantly hone those skills to a point of perfection. If you commit to doing this, the people who lead you will no doubt know where to turn when they need your skill set.

3. Collusion will kill your integrity

Every day at work isn’t golden…and that’s ok. It’s what you do when you feel this way that’s important. Whenever we encounter a difficult situation, it’s all too easy for us to turn outward and blame our organization, our leader, the people we manage, etc. This usually results in gossip and/or reactions seated in anger/frustration. There is nothing that tears down a team quicker. Instead of turning out, turn inward. Reflect on why your day didn’t go well and make an action plan for how you’ll improve the next day. If things still aren’t going well, bring your concerns/frustration to those that lead you. Chances are, together you’ll find solutions to improve on situations that are making you unhappy.

4. Communicate often & effectively

This one might sound cliché but it’s one of the most essential lessons that I’ve learned in my tenure in the ‘real world.’ Often times we hold information that we think that everyone knows when in reality this isn’t true. The more we communicate, the more opportunities we give to those on our teams to help clarify our ways of operating. If questions arise that you don’t know the answer to, it’s ok to say “I don’t know,” if you don’t have the right information to communicate, it’s ok to say “I don’t have that answer for you, can I follow up with you when I do?” And then follow up! If you do this people will see you as having integrity and will listen to your communication with more trust. Communicating often helps build transparency so that everyone has the same information. No one wants to be seen as disingenuous; saying one thing to some and another to others.

5. Lead with grace

Chances are, if you’re a highly performing leader that people say “thank you” often. Respond with a gracious “you’re welcome” and give them concrete reasons why/how you were able to perform a given task so well. Too often I’ve received “thank you” messages and let them sit in my mailbox. It doesn’t give people the courtesy of having their thank you acknowledged. When you make a mistake, own it immediately. The longer you try to hide your mistake the more catastrophic the fallout will be when it is uncovered.

I’ve learned much more than 5 lessons in the past 2 years but these are the ones that I hold most dear to my becoming a better leader, learner, and doer. I challenge you to leave lessons that you’ve learned in the comments below.

Happy Commenting!

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