14 things I would tell my younger self if I could go back in time

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Hi everyone, happy December. I do a lot of speaking, and a question I get asked often is “If you could go back in time to earlier in your career, what would you tell your younger self?” This is when you know that you are getting old, when people ask you this question. It is a badge of hard-earned wisdom. So, here, in no particular order, are a few things I would tell myself, gathered from experience and failures in the field, and from working with much smarter people: 

  1. Have the audacity of ambition, even if people doubt you or laugh at you: The scope of injustice and inequity is so large, so our ambition must be large enough to address it. Dream big. Be unapologetic. Especially if you come from marginalized communities and have been told you should settle for crumbs. Don’t. Go ahead and add a zero or two to your grant requests. 
  2. There is a major difference between doing things right and doing the right thing: Peter Drucker said, “Management is doing things right; leadership is doing the right things.” The former is about processes, filling out the right forms, following the laws, etc. Doing the right things is often harder and sometimes goes against established laws and rules, but this is often where we find our humanity.
  3. It’s OK to acknowledge that you suck at some stuff: Because of the ineffective way nonprofits are resourced, we’ve had to “wear many hats” and do everything. It’s good to develop skills and improve on things you’re weak at, and it’s also good to acknowledge some things just don’t come naturally to you, and that’s OK. Being aware of your strengths and limitations allows you to find colleagues whose skills complement your own.
  4. Many things society considers weaknesses are often strengths: On the other hand, society has a bias toward certain people and qualities. For example, extroverts and organized people. But some of the best leaders are introverts. And if you’re “chaotically creative” like I am, you might feel terrible, but that there are plenty of research that shows that those who are messy, forgetful, etc., are often very creative and are able to come up with solutions others may not think of.  
  5. Many “best practices” are inequitable and we need to reexamine them: In the beginning of my career, I accepted many things I was taught as sacred and immutable: Board governance structures, fundraising tactics, hiring practices, Robert’s Rules of Order, etc. But many “best” practices are only best for those with the most privilege in our society and often reinforce inequity. Do not accept any “best practice” as gospel; stop and ask who determined that it’s best and whom does it most benefit.
  6. Self-sacrifices are not always noble; they often harm others: For years I thought I was doing my organizations a favor by taking salaries way below the average when I was the ED. I was harming other colleagues through depressing wages and setting bad precedents. Advocate for equitable pay and benefits, paid family leave, retirement matching, etc., including for yourself if you have formal leadership roles. Take vacation time and mental health days. Being stressed and underpaid is not a badge of honor.
  7. It is worse to give people false hope than to give them no hope: It some of the toughest times, such as during leadership transitions or cashflow issues, I had the urge to say things would be OK. Sometimes things are not OK. Sometimes things are terrible, and it’s gaslighting to say otherwise. Respect people enough to be honest with them.
  8. Things are rarely binary; they are often interdependent: Polarity management theory has been really helpful to me, and I wish I had learned it earlier. Things that seem contradictory often co-exist and are interdependent, especially in a field as complex as ours. This can be applied to many areas, from interpersonal dynamics such as colleagues not getting along, to systemic issues.  
  9. Be aware of power dynamics and how you yourself wield power: Each of us holds some degree of power, and it’s important to constantly check and, if needed, mitigate the effect it has on others. Formal power, such as a position you hold, is more salient, but there is also power that comes with being white, male, educated, non-disabled, cisgender, heteronormative, higher-income, English speakers, neuro-typical, etc. No matter how nice and humble you are, there are always power dynamics to watch for.
  10. You cannot do this work well and not piss people off; just make sure it’s the right people. If you do the right things, such as challenging unjust systems, you will likely make people angry, especially people who are focused on “doing things right.” This is a sign that you are making progress, and if no one is ever mad at you, that’s a sign that maybe you’re not. Just make sure the people who are pissed off are people who tend to hold privilege and power in society.
  11. Do not let your mission get in the way of your vision: Organizations have missions and visions, and so do individuals. Our visions tend to involve making the world a better, more just, more inclusive place. Our missions are about how we go about doing that: raising funds, growing our team, running programs, etc. But it’s easy for orgs and individuals to be so consumed by the mission that they forget about the vision, and end up further away from their original vision.
  12. Keep serving people the Brussels sprouts of equity: Research shows that it takes 5 to 10 exposures to a new food before a toddler may develop a taste for it. The work of creating an equitable and just world feels a lot like feeding vegetables to picky toddlers. You may get frustrated and think that your efforts are futile when your board or supervisors or teammates reject your ideas, but the reality may just be that you delivered the necessary third or fourth exposure, and it may be up to other people to pick up the spoon.
  13. Resting, recharging, and finding joy and humor in the work are vital to the work: The work we do is often difficult, heartbreaking, and draining. It is also amazing, exciting, and meaningful. To do it well, we must rest and recharge and find moments of joy and humor. And we need to let go of the guilt we feel when we do these things.
  14. The time you have with the people you love is shorter than you realize: Children grow up quickly. Parents and siblings age just as fast. And people die suddenly, even the people we love. If I could go back in time and could only tell myself one thing, I would say, “Spend more time with Mom; don’t say no when she invites you on her afternoon walks or to run errands with her.” In my last few memories of my mother, we walked around our neighborhood, and she told me she wanted to see “Million Dollar Baby.” We never got to see it; she died a few months later. The work will always be there; the people we care most about may not.

I hope that was helpful. Though, to be honest, if I really could invent a time machine, I’d probably just tell myself to invest in some carbon-neutral cryptocurrency, become a multi-millionaire, and then retire early, somewhere secluded but with access to wifi for streaming episodes of “Bob’s Burgers.”

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