A Response to Iain’s Letter to His Younger Self

From time to time, Ann Oliva is taking over my blog as part of her Leader in Residence role with OrgCode. Despite having different leadership styles and career trajectories, Ann and I share a passion for cultivating leaders in the pursuit of ending homelessness and in leadership driven by values. I hope you enjoy reading Ann's guest blog as much as I did.

Last March, Iain wrote a blog post called "A Letter to Myself of 15 Years Ago" that I found particularly compelling for both the similarities and differences in our leadership experiences.  I bookmarked the post with the vague idea that I might one day have the chance to respond with my own thoughts.  I figure now is my chance.

Dear myself of 15 years ago  –

Hi Ann.  I have been thinking a lot lately about what advice I might give you as you find new ways to work towards your goals and dreams.  You are stubborn and I am not sure if you will even take this advice – and to be honest I am not sure that you should.  The journey I took is the one that made me who I am today – as you know I am a big believer in learning something from each and every experience you have, good and not-so-good.  But I do think I have some important things to remind you of as you take that same journey.

I know you haven’t realized it yet, but you are a natural leader.  Your willingness to raise your hand and challenge the status quo even when the hand you raise shakes, your ability to think through solutions based on a core set of values that don’t waver, and your desire to take risks when it makes sense will put you in a position to lead down the road.  You will have obstacles ahead that make you question your role, your value and your impact.  There will be days when you ask yourself just what the hell you are doing.  Do not let those situations deter you. I know that you are a bit reluctant to embrace a role that puts you at the center of attention.  You like to work behind the scenes, making things happen and letting others be the face of the work.  That’s ok, but eventually you will need to step out and communicate with your team, your community, your stakeholders in a way that explains the why and the how of the work you create.  Practice in smaller settings and work your way up to larger groups.  Find a communication style that works for you and stick with it.

Learn everything you can from each and every leader you meet and work with.  Learn what parts of his or her style work for you, and maybe more importantly tuck away in the back of your mind the things that you don’t think work – things that made you feel small or not valued by someone in a position of authority.  Don’t do those things.

You are going to make mistakes – small ones and some big ones.  This is part of learning and if you are not making at least some mistakes you are not doing it right.  Do not let them paralyze you.  Accept responsibility for them, apologize if you should, and move on.  But be balanced in your approach to mistakes - don’t over-apologize, internalize too intensely, or take responsibility for mistakes that others should own.  Accountability should be applied to yourself as well as those around you for it to be meaningful.

Leadership is not about power.  If done right, being a leader means you are influencing others in a positive way.  Figure out how to use your platform – whether that is with a non-profit serving those experiencing homelessness, or in the federal government, or anywhere in between – to influence those who are both up and down the chain of command.  Because you don’t have to be the CEO to be a leader.

Be self-aware enough to see your own shortcomings and find people to have around you that fill those gaps.  You are stronger and more effective when you are surrounded by smart, empowered people who share your goals and vision.

Be kind to everyone, but also be firm when you need to and communicate directly as often as possible.  Try not to let your passion for the mission spill over into anger when things get tough or frustrating.  But being kind does not mean backing down when you know you are right, or allowing yourself to be talked over, put down or insulted.  Handle conflict with grace and respect, and others will likely treat you with respect.  For those that don’t, be direct but do not expect what they are not willing to give.  You learn to work around those people, or through them. Or become their boss.

Each and every relationship you have builds your network, and your network can make or break you as a leader. Be willing to share some of yourself with people, and learn about the lives of those around you. Nurture and tend to your relationships even when you are an introvert who just wants to go home and sit on the couch. 

Try not to work every weekend and on vacations.  Take a break when you need it, or 15 years down the road you are going to have to take four months off to recover, and it will take two months of that break to even start feeling human again.

One day, at a particularly trying time in your career, you are going to tell a close friend that you want to quit and start working at Pottery Barn to get away from the stress and responsibility that comes with command and leadership.  She will turn to you and say – if you work at Pottery Barn you will just end up running Pottery Barn.  So you might as well use your inclination towards leadership to have an impact on the thing you are passionate about.  She is right.  Be grateful for the privilege of leading others in this work that is so important to all of us.

In short, self of 15 years ago, leadership is hard and there is no magic potion that makes the hard stuff easy.  But it is worth the effort. Remember to be brave. Never be anything but yourself, but don’t take yourself too seriously.  Embrace your natural leadership skills and have some fun with it.  See ya in 15 years.

Ann