What I Learned About Leadership Last Year By Making Mistakes

Written by
Erin Roberts
Published on
January 4, 2023
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 camping in forest during nightime

Image Credit:  

Denys Nevozhai

“You have to make mistakes to find out who you aren’t. You take the action, and the insight follows: You don’t think your way into becoming yourself.”

- Anne Lamott -

"Take risks. Ask big questions. Don’t be afraid to make mistakes: if you don’t make mistakes, you’re not reaching far enough."

- David Packard -


I made a lot of mistakes last year. And I do mean a lot. So, so many. This fact really cannot be overstated (but I think you get the point). But I also learned a lot. And I do mean a lot. This fact also cannot be overstated. Do I still regret some of the mistakes I made in the chaos of 2022 and wish that some of them hadn’t exacted a toll on humans I care deeply about? Heck, yes. But did learning from them make me a better human? Also, yes. And did those lessons help make me a better colleague, a more capable leader and the initiatives I lead more effective vehicles for cultivating change?  Well, that remains to be seen but I sure do hope so and between you and I, it’s looking good so far. However, the memories of overwhelm are still fresh, so I remain cautiously optimistic. As I process the ups and downs of last year in the early days of this year, a few key lessons have emerged which I’d like to share with you.  

Change truly is an inside job

Making mistakes is part of life. And as Sophia Loren said, “mistakes are part of the dues one pays for a full life.” But learning from them? That’s where the real magic happens. Henry Ford took it a step further in arguing that: “[t]he only mistakes are the ones we don’t learn from.” However (and this is critical so lean in closely) to learn from our mistakes we first need to do the internal work that allows us to separate who we are from the mistakes we make.

Our mistakes are not us. Even though we might recognize that on some level so many of us translate mistakes into meaning that we are inherently bad. And that’s not okay. Mistakes are part of being human and each one provides us an opportunity to learn and grow and live a more expansive, full life.

To illustrate this point, I stand on the shoulder of a giant: the amazing work and wisdom of researcher Brené Brown who has done extensive research on this topic in her academic career. I would highly recommend checking out her many books, Ted talks and podcasts (both her own and her guest appearances on others) if you want to learn more particularly about the importance of vulnerability. Her work on shame is equally powerful and has been pivotal in elucidating the difference between shame and guilt. In her second Ted Talk Brown differentiates between the two with this description:  

Shame is a focus on self, guilt is a focus on behavior. Shame is “I am bad.” Guilt is “I did something bad.” How many of you, if you did something that was hurtful to me, would be willing to say, “I’m sorry. I made a mistake?” How many of you would be willing to say that? Guilt: I’m sorry. I made a mistake. Shame: I’m sorry. I am a mistake.

Once you get this fundamental point you can see mistakes as a gift. However, loving yourself will help expedite this process of learning from your mistakes; and in my view is an essential element. I find that the more I love myself and embrace who I am as a human, the more I’m able to see mistakes as the lessons they are meant to be. Do I intentionally make mistakes? Definitely not. But I also don’t dwell on the making of the mistake but rather what they can teach me and how I can leverage them to grow in both my personal and professional life. Indeed, as Alex Mathers writes in an article on Medium, mistakes are our most reliable teachers. And if you’re not making mistakes, you’re not taking enough risks in life. We should see them as the guideposts and indicators they are that we are taking risks, trying new things and just generally living life.

Leaders go first

One of the takeaways of both my academic work on leadership and my observations of people I consider to be good leaders is that leaders lead by example and that means going first. I first learned about “going first” from athlete and entrepreneur (read all around badass) Gabrielle Reece in her conversation with Tim Ferris, lessons from which he included in his book Tools of Titans. In her first conversation with Ferris, Reece explains what it means to go first:

I’ll go first. If I’m at checking out at the store I’ll say hello first, if I’m coming across someone making eye-contact I’ll smile first. Not all times, but most times — it comes in your favor.

Writer Tré Wee also interviewed Reece and writes about his experience with going first in an article on Medium. He reports that going first allowed him to identify the people he wanted to spend time with (and those he didn’t) and enabled him not to have expectations of how people would respond.

Going first is fundamentally about deciding how you are going to show up in the world regardless of what others do with it. It allows us to say this is who I am. And once again, a foundation of self-love is imperative as it allows us to care less about how others see us and more about how we see ourselves and most importantly, how we show up in the world. I take kindness very seriously. I want the people who take the time to engage with the initiatives I lead to feel not just seen and heard but also held. But I'm also quirky and as I've written about in a previous blog, I have a way of seeing and experiencing the world that is different than many. Last year I had to remind myself that I can be kind, empathetic and quirky while also being strong, empowered and assertive. This has been huge for me and is a lesson I’m still operationalizing.

Another theme as I’ve reflected on 2022 is the power of being authentic and honest about my struggles. One of my proudest moments of last year occurred during the last call of the year with the young negotiators I work with in which I apologized for all the mistakes I made during the course of the year (some of which were very recent) and committed to learn from them. I knew that some of those mistakes were game changers and the lessons they provided have already changed the way I live and work. In being honest about my mistakes I helped create a space where others can do the same and modelled the importance of learning from our mistakes.

I am also proud of the way I embraced extreme ownership last year more than ever before. Extreme ownership is a term coined by Jocko Willink and Leif Babin in their book of the same name, and occurs when leaders take responsibility for everything that happens within the teams that they lead. I once heard someone say that losses belong to leaders alone and wins to the whole team. This is the idea behind extreme ownership. I’ve heard Willink say both in interviews and on his podcast multiple times that “all problems are leadership problems”. This is something that has stayed with me and motivates me to be a better leader.

This year I took more ownership for the mistakes that were made in the initiatives that I lead – because at the end of the day they were mine. However, in order to take extreme ownership you need to be able to practice what I would call extreme humility and be open to showing your vulnerability - and that takes work. For me this continues to be a work in progress, but I came a long way last year and I’m proud of that.

Have the hard conversations early and often

The most profound lesson of last year and the one that has forever changed me is that I need to have the hard conversations much, much earlier before situations escalate and relationships deteriorate. Like many people, and probably most women, I don’t like confrontation. That sometimes comes as a surprise to people because I so often speak up about the issues I care about and having worked on highly political issues throughout my career, I’m no shrinking violet. But in my own daily life, both personally and professionally, I have tended to avoid difficult conversations. Instead, I let issues fester and they inevitably become worse.

Last year I paused some professional relationships (I like to think they are on pause rather than ended) l because things had gotten so bad that I couldn’t see any other option. I could have avoided a lot of pain, both for myself and others, by just being honest when things started going array. I’ve committed to be a better example by confronting challenges before they become problems and have asked my colleagues to do the same; even if that means I am the one that they need to confront.

The importance of creating space for responses rather than reactions

Oprah Winfrey maintains that life whispers to us all the time and the longer we ignore it the louder it gets. I’ve gotten better at listening to the whispers, but as I indicated above, I’m still letting them get too loud. And by the time I listen life is no longer whispering but shouting. As a result I sometimes make decisions rashly because I cannot live one more moment in the discomfort I’ve been ignoring for too long. This hurts relationships and isn’t good for the initiatives I lead nor for the people I work with. This was the most confusing lesson for me though I’ll admit, and here’s why:

We often use the phrase “listen to your gut” which is I believe what Winfrey is referring to when she talks about life whispering to us. And while I completely agree, I don’t know about you, but my gut doesn’t come with a road map. When I do listen to my gut I know what the right decision is but I don’t necessarily know how to make it.

Last year I made some right decisions in the wrong way. Had I listened to my gut a lot sooner I could have created some space to respond rather than react. Writer Leo Babauta describes the difference in a blog on his website Zen Habits. Reactions are fueled by emotions and quickly follow a triggering event while responses are more thoughtful and occur some time after the triggering events, perhaps minutes, hours or even days.

This year I’ve committed to set better boundaries and have the difficult conversations much earlier. And if I fail to do that and my gut tells me a situation must be urgently addressed I will still endeavour to take the time needed to respond rather than react. My meditation and mindfulness practice will invariably be helpful in this, though I know it won’t always be easy.

Just be here now: The power of mindfulness

I have long been – some would say obsessed – with evolving as a human being and known to add tools to my toolbox with regularity. I’ve walked over hot coals at a seminar with Tony Robbins in New York, meditated with hundreds of others at a workshop with Joe Dispenza in Dublin and have seen Elizabeth Gilbert, Eckhart Tolle, Deepak Chopra, Danielle Laporte - among many others – speak in London, my home base. I’ve taken online courses with Bréne Brown, Shawn Achor and Byron Katie - among many others. I’ve had half a dozen coaches and more than a dozen mentors over the past few years. Throughout the work day when not on calls I listen to podcasts. If there is a chance it will help me grow, I am here (or there) for it. And while that has been transformative on many fronts it’s also exhausting. It felt like I was always chasing something, never good enough.

In the fall I started working with a new coach who has a different approach which is just to be in the now as much as possible. I speak with her once a month and between sessions my homework is to do daily meditations and just to be in the now as much as possible the rest of my waking hours. That’s brought me back to mindfulness which is in the words of Jon Kabat-Zinn, who is considered by many to be the founder of the modern mindfulness movement,  is, “paying attention, on purpose in the present moment without judgement”.  

During a particularly stressful time in undergrad I took a mindfulness course which helped me enormously at the time and I kept using some of those tools like meditation but others fell away. Over the last few months I have revisited and upgraded those lessons.  I am blessed to have a subscription to MasterClass and recently took Kabat-Zinn’s class on mindfulness. You don't need to take his MasterClass though to begin practicing mindfulness. All you need to do is focus on the now, not the past or the future but this moment right here. Your monkey mind will come up with all sorts of reasons for you not to focus on the here and now. Just watch those thoughts without judgement is what Kabat-Zinn recommends. Being mindful might be the hardest but also the most important thing you ever do.

As I’ve started to integrate mindfulness more into my workday I’ve noticed how much calmer I am and how much less apt I am to react. I am also happier. In another article on Medium Alex Mathers argues that when we stop searching we become happier. He writes that:

If we’re knowingly pursuing the illusion of ‘happiness’, we are unwittingly communicating to ourselves that we’re — you guessed it — not happy.

I hope I’m also a better colleague and a more effective leader as a result of integrating mindfulness more into my workday – but like all things this is a work in progress.

Embracing the messiness

I wish we talked more openly and honestly about how challenging it can be to start new things and just how messy life can be. Building initiatives from scratch as my colleagues and I have done and are doing is difficult, especially if, like us, you don’t have a safety net. While we have institutional partners, the initiatives I lead are not hosted by institutions. And while there is a silver lining in that this motivates us to hussle, it also means that things aren’t very structured and that a lot of the work is unfunded - at least in the beginning.

Last year in the midst of all the chaos someone I work with told me repeatedly that we need processes and systems in place to better organize our work in one of the initiatives I lead. I completely agreed but at the time we were still building the initiative and to be honest this feedback felt pre-emptive and a little unkind. It felt a little like criticizing a house for not yet having furniture when the foundation had just been laid. Yet, instead of zooming out and understanding where this feedback was coming from (someone who was used to working in a very structured environment), I took it to heart and let is make me feel like something was wrong with me.

And then I remembered all the podcasts I’ve listened to and books I've read over the years in which entrepreneurs stressed how difficult it was to establish their companies and build their brands. They told tales of sleeping in their offices and paying themselves pennies an hour for years and stressed the sheer amount of grit and hustle that it takes to start something new and the incredible perseverance it takes to wake up each day and do it all again. This quote from Susan Wojcicki, the CEO of Youtube, also helped me feel better about my own professional challenges:  

Rarely are opportunities presented to you in a perfect way. In a nice little box with a yellow bow on top. ‘Here, open it, it’s perfect. You’ll love it.’ Opportunities – the good ones – are messy, confusing and hard to recognize. They’re risky. They challenge you.

Another important reminder comes from a speech by former US president Theodore Roosevelt called Citizenship in a Republic which he gave on several occasions during a tour of Europe in 1910 after leaving office in 2009. When I present my academic work on leadership I always start with an excerpt from this speech because it demonstrates the realities so perfectly:

It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.

Taking risks, starting new things and living a full life can be messy. But there is honour is being in the arena and doing our best. The lesson I’ve learned this year is to not just own the messiness but to talk about it more with others. Recently I watched broadcaster Robin Roberts' Masterclass in which she talked about some of the difficult times she went through and grappled with whether or not to make her struggles public. Her mother advocated for being the voice of those who don’t have a platform to do so and to “make the mess your message”. This resonated with me so much and I’ve vowed to make the mess my message too.

If you cultivate it, self-love will become your superpower

While certainly not my most difficult trip around the sun, last year was still challenging. I have always known that I have grit to spare and that has sustained me in difficult times. What is special about this past year is how much I’m able to revel in the lessons that came in the aftermath of the many mistakes I made rather than beat myself up about making them in the first place.

I often say that my heart is my superpower and that’s still true. The more I love myself, the better I’m able to learn lessons and take them forward. Thanks to all the inside work I’ve done I am now able to separate my mistakes from who I am because I love myself more now than I did a year ago. And that’s the real lesson of this past year and the real work of our lives. To love ourselves no matter what. If there is one thing I hope that you take away from this blog Dear Reader it’s that you are already perfect. Making mistakes might help you live a more vivid life, but it won’t change that fact.  

Erin Roberts it a climate policy researcher and strategist and the convenor of the Climate Leadership Initiative. In her work on all fronts, she aspires to empower young change makers from the global South to make even greater change. This work starts with teaching the power of self-love, something that is very much a work in progress in her own life.