How Doing Hard Things Made Me A Better Leader

Written by
Erin Roberts
Published on
February 2, 2023
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Hikers at the bottom of mountain peak (Black & White)

Image Credit:  

Johnathan Bell

“First say to yourself what you would be; and then do what you have to do.”

-  Epictetus -

“Choose not to be harmed and you won’t feel harmed. Don’t feel harmed and you haven’t been.”

-  Marcus Aurelius -

“How does it help . . . to make troubles heavier by bemoaning them?”

-  Seneca -

If you asked me a year ago if I was a good leader, I would have said something along the lines of: No way José (because I’m sophisticated like that). If you asked me six months ago, I would have said: Heck, no. Two months ago, I would have said: Not yet but I’m getting there. And if you asked me today, I would say: Yeah, and every day I get a little bit better. What changed? Well, a lot of things to be honest. But the most relevant is that I made a conscious decision to become a better leader. The journey to becoming one involved many different things one of which was doing hard things on purpose both successfully and sometimes not so successfully because there are lessons in both. This blog is about what I learned and how I operationalized those lessons in my work to be a better leader and how doing so has also made me a happier person.

Knowing is very different than doing

I literally have a PhD in leadership (technically it’s in geography but as my friends and family know I have difficulty navigating the world without and sometimes even with Google maps, so I rarely advertise that fact). I decided to study leadership because I was fascinated by leaders and still am. Not because I ever envisioned myself as a leader. But because I was curious about what makes a leader a leader. What qualities do they have and how do they develop them? Can leaders be developed or are they born (the age-old nurture versus nature)?  Similarly, I founded the Climate Leadership Initiative because I wanted to create a vehicle for empowering young leaders from the global South, not because I envisioned myself as a leader.

Then, three years ago, I found myself somewhat accidentally at the helm of a fast-growing initiative. The fact that I was at the helm was not an entirely an accident as I founded the initiative in the first place. But it became much bigger and was growing much faster than I had ever envisioned and that was uncomfortable. Because suddenly I was leading a team. I had long been what I would consider a pretty good team member but rarely had I led teams.  One of the reasons as I’ve written in a previous blog is that my brain functions differently than most and I don’t jive very well with business as usual. I felt ill-equipped and way out of my depth to lead a team. And that was quite frankly scary.

But if I was going to see things through, I needed to get over my fear and get on with the business of figuring things out. So, I did. I read dozens of books and hundreds of articles and blogs. I listened to podcasts. All. Day. Long. I binged on MasterClass the way many people binge on Netflix. [In case you’re wondering which classes that I learned the most from are from two iconic basketball coaches: Mike Krzyzewski (also known as Coach K) and Geno Ariemma.] And that was all great and having knowledge did help me. It really did. But that knowledge for the most part also largely stayed in my head until I put it into action.

Over a year ago I made the decision to operationalize what I had learned and that looked like trying different things and seeing how they worked in my life and in my work. It felt awkward and uncomfortable at first and probably looked awkward and honestly, it still does a lot of the time.  But I keep going because I can see now how far I’ve come. Venturing into new territory is always going to feel uncomfortable at first but that’s how we grow. One of the things that helped me grow the most is doing hard things on purpose. Sometimes I succeeded and other times I failed – but each time I took something valuable from the experience that made me a better leader. As author James Clear says in Atomic Habits, if you improve one percent each day you end up 37 times better at the end of the year (Clear, 2018).

We can do hard things

One of the gifts of the pandemic was that it gave me more time to contemplate and reflect on who I want to be and how I want to show up in the world. I started to think about cultivating my own resilience and mental toughness. What might that look like? I also wanted to keep promises to myself. Months into the pandemic, like many people, I felt untethered. I’m someone who, like so many you I’m sure, can push myself hard on the work front which leaves little in the tank for other things. I decided that part of being resilient is setting better boundaries. The change that has followed that decision has been incremental but incrementally positive is in the right direction. In 2021 I decided to start walking in the country every day, sometimes for several hours a day as I started taking some of my calls while walking. In the middle of last year, I started to carve out time for the gym several times a week, usually in the early morning. And then at the start of this year I promised myself I’d do yoga every day.

If you think that sounds easy you should know that before I started this challenge, I hated yoga with the intensity of 10,000 fiery suns. It represented so many things I felt I wasn’t. Mainly, flexible. But I told myself I would do it every day, and so I did. And by the second week it was something that I looked forward to. [Side note: If you’re looking for a great at home yoga guide you could do no better than Yoga With Adrienne. She’s quirky and kind she cool dog.] A week into the Yoga Project I started to override the lazy, inflexible part of me which doesn’t want to get on the mat and now a month into the new year it’s a habit.  

Not all of the hard things I have set out to do have gone well, though. Last year I decided to take up boxing, something I’ve long wanted to do because – why not?  I’ve long been fascinated by the mindset of boxers, particularly that of Mohammad Ali who was dedicated, hard working and by all accounts a very happy person. I found a boxing coach and started training with him and it’s been great so far and relatively simple. I show up once a week on a Saturday morning to work on skills and during the week I do conditioning. Until recently. Because a few weeks ago my coach said to me (something I literally never thought I’d hear someone say to me ever): We’ve got to get you punching something.

As I pondered what it meant to “punch more regularly” my coach asked me if my gym had a punching bag. I replied that it did. But I also recalled that it was in the middle of the floor where people warm up, cool down and do floor exercises and it’s also surrounded by machines. In other words: not private. And very much out of my comfort zone because I’m still learning how to box. So I offered alternatives. I could punch my mattress. I swear to the goddess I said exactly that and to his credit my coach kept a straight face. I was desperate, okay? I suggested that there must be some kind of an apparatus that I could fashion to the wall – a punching wall? But if the punching wall exists I couldn’t find it. So, we circled back to the idea of using the punching bag at the gym.

I started scoping the punching bag out in the morning when I’d go to the gym. As I did my workout I’d occasionally check out how many people were around the punching bag. How visible would I be? How much noise might it make? How much attention would I draw?  I was already going to the gym at 5 am and there was already a small and growing crowd there at that time. By 6 am the gym is buzzing. So, I started making the intention of waking up earlier so that I would encounter fewer people and could punch my heart out without being too self-conscious. I would set my alarm for 4 am but invariably change it just before going to bed when I realized I wouldn’t have a prayer of getting enough sleep to get through the next day if I followed through with my plan. My boxing gloves and wraps would sometimes make it into my gym bag the night before, but they would inevitably get taken out the next morning when I hadn’t managed to wake up at 4 am.

I told this all to my coach when he asked me about my progress the next week, which happens to have been just last week as I write this. He was empathetic. But he also said you’re not going to get better if you don’t practice punching more. Once a week is not enough. He said this is one of those hard things you need to do and you’ll be happy you did (as you’ll find out below he already knew I was doing hard things on purpose) So, I told him confidently in my bravado that the next week, which is now this week I would do better. I said next week I’m going to punch the bag three times (three sessions not three punches - just to be clear). He said I’d be happy with once but even if you don’t it’s okay. A few hours ago, he messaged me to ask how this week was going. I replied that I’ve been on the struggle bus this week and have only made it to the gym once (which is unusual for me). He said, well I guess that means we’ll be working harder on Saturday. I’m guessing that means I have a lot of burpees in my very near future.

What I didn’t tell my coach is that one of the reasons I’m struggling so much this week is that I haven’t been sleeping well. I didn’t tell him that I was still in my pajamas when he messaged because I’d gotten up early to get work off my plate – the opposite of what I preach. I didn’t tell him that my flat is a disaster. I didn't tell him that the reason it’s been a particularly difficult week is that the initiatives I lead are both in a funding crunch and I need to mobilize funding quickly to keep the lights on so to speak. But more than that I’m worried about the amazing people I work with who drive the work we do. What keeps me awake at night is worrying that they won’t be able to pay their mortgages, their rent, keep the lights and the heat on and put food on the table. One of my colleagues closed on a flat today and all I could think about was how can I keep them funded so that they can pay their mortgage? It’s making me ill. I’m making me ill. And I know that getting to the gym and punching that bag would invariably help – but today I just feel sad and I can’t make myself get out of my sweatpants and into my gym clothes.  And today the hard thing is letting that be okay. And telling you about my struggles.

In 2020 just before the onset of the COVID-19 pandemic which changed life as we knew it forever, writer and thought leader Glennon Doyle’s book Untamed was released into the world. It is a beautiful book. It read like a heart broken open that says: Here. This is my truth. I hope it can help you. In the book Doyle recounts a difficult time in her life and how her mantra became: We can do hard things. She writes:

. . . I am a human who is finally doing life right. “We can do hard things” insists that I can, and should, stay in the hard because there is some kind of reward for staying. I don’t know what the reward is yet, but it feels true that there would be one, and I want to find out what it is (Doyle, 2020).

During this difficult time, as she walked through this fire, Doyle recalled:

I say to myself ever few minutes: This is hard. We can do hard things. And then I do them (Ibid).

She continues by recalling that she was particularly comforted by the “we” part. Though she didn’t know who “we” was at the time, she needed to believe that there was a “we” and that became a lifeline of sorts. And in her own words, that became a “rallying call” for many people during a challenging time.

Together with her sister and wife, Doyle hosts a podcast called We Can Do Hard Things. Part of their message is that in being authentic, honest and real about our own struggles we can help others. This resonates with me today. Sometimes we do hard things and that makes us feel better and sometimes we try and fail. Some days life is beautiful and exciting and some days it’s just hard. Today I’m reminding myself that we can do hard things and that there is indeed a “we”. I’m not alone in my struggle, today or any other day.

Embracing the Stoic challenge

I’ve long been interested in the philosophy of the stoics, particularly Marcus Aurelius, Seneca and Epictetus, three very different men with similar ways of both seeing the world and living their lives. I long thought that the stoics were well, stoic, which is defined in the Oxford Dictionary as, “a person who can endure pain or hardship without showing their feelings or complaining.” Key in that definition is the phrase “without showing their feelings”.

However, in his book The Stoic Challenge, philosophy professor William B. Irvine challenges that narrative, maintaining that though we might think of stoics as:

Emotionless beings whose primary goal was to stand there and grimly take whatever life threw at them, but this was not the case. Their goal wasn’t to banish emotion but to minimize the number of negative emotions – such as feeling of frustration, anger, grief and envy – that they experienced. They had nothing against the experience of positive emotions – including delight and even joy (Irvine, 2022: 17).

Irvine explains that the primary goal of stoics was to experience tranquility and thus they avoided experiencing negative emotions while continuing to enjoy positive emotions. According to Irvine, Seneca said that wise people welcome adversity as a training exercise and might even “take delight in it” (Ibid). The stoics didn't only see opportunities in challenges that naturally happened, they actually sought them out. And not only to make them tougher or more resilient but to make their lives more joyful. And the primary way they did this was by not allowing negative emotions when encountering a challenge. Think about that. They didn’t just not react when they became angry or frustrated. They didn’t get angry or frustrated in the first place. Imagine how much freedom you would have if you didn’t react negatively to all the little challenges that arise every day. This book has been a game changer for me. The stoics would tell me there is no point being sad about the funding conundrum – just to see the opportunities in the challenge. And they would be right. Because what’s the point of being sad? Really (except that it justifies staying in sweatpants all day).

A few weeks ago I made the catastrophic mistake of telling my boxing coach that I was doing some research on stoicism and was purposefully doing hard things as a way to grow and evolve. That’s part of what drew me to boxing in the first place so it wasn’t a huge surprise to him. The following week I gave him my hard copy of The Stoic Challenge as I thought it might help some of the boxers he works with.  I was confident that I was already well underway in my own journey of embracing the stoic challenge. I was taking the long way home from boxing and taking harder hiking routes than usual and challenging myself a bit more in the gym. Looking back now I can see how deluded I was. I got the challenge in theory but not in practice. I hadn’t really challenged myself. I already went to the gym and hiked regularly and walked home from boxing. Sure, yoga was new and it was challenging to get it in every day because of my extreme aversion to it. But it was also in the comfort of my own home. No one else saw my discomfort. Enter the punching bag which became my ultimate (for now) stoic challenge but not the only one I’ve willingly taken on in recent weeks. The stoic challenge helped me to see the opportunities in the many interactions I have in my every day. Not allowing challenges to give rise to negative emotions in the first place is already profoundly changing the way I work and live.

First put down your sword

Recently I was anticipating having a difficult conversation with a colleague and I felt very angsty about it. Over and over in my head I kept envisioning this conversation and seeing myself getting defensive in my mind’s eye. So. Not. Helpful. And it didn’t feel good in my body either. I felt tense all over. And when I realized that I was literally making myself ill thinking about what I anticipated would be a difficult conversation I asked myself: how could this be different? What is the lesson here? And then I remembered two things.

The first is the stoic challenge and the fact that there are lessons in challenges. If this is a test, then I had already failed by anticipating a difficult conversation. What if I took this challenge as an opportunity to grow and what might that mean? Well, I need to show up differently. But how? The second thing I remembered what I’ve learned in my research on radical collaboration which is that one of the major obstacles to radical collaboration is defensiveness. So, what if I didn’t get defensive. What might that look like? What if I just showed up and said where are you at? What’s going on with you?

Before the conversation was to take place, I literally imagined myself removing my armour as if I was an ancient warrior. My heavy metal helmet was the first to fall on the floor with a loud clunk. Then the breast plates came off followed by the shin guards. Finally, I unsheathed my invisible sword and tossed it to the side. There, I was now ready for the conversation. And you know what, it went brilliantly. Better than I could ever have imagined. So, I kept shedding my invisible armour before each conversation even if it might not be one I envisioned as difficult. Each time I asked myself: how could I show up and just be of service to the other person?

Now I don’t need to imagine the process of shedding my armour. I just show up to each conversation with a curiosity with the intention of making the other person’s day better. This is relatively new so it’s very much still a work in progress. But a few days ago, I asked a colleague for a call to ask how things were going. I had also intended to deliver a piece of constructive feedback as I’d committed to confront anything that might become difficult long before it actual became difficult (if that makes sense) which I wrote about in a previous blog.  There wasn't anything that was difficult yet but I thought it would be good to check in. But before I could do so, they gave me a piece of constructive feedback. And you know what? It lifted me up. Not because they delivered it in such a beautiful way, although they did. But because it excited me to know there was something I could change which would automatically make me a better leader. First because it showed I listened and cared and secondly because in addressing the thing i was doing and not doing it any more - I became an easier person to work with.   I saw the challenge and I rose to it. Was it easy? No. But it was simple. And it’s definitely made me a better colleague too. I was able to do that because I decided to see opportunities in the challenges, certainly. But also because I love myself enough not to feel shame when I have done something wrong.  And that’s made all the difference.

Sometimes the lesson is in failing

This blog did not go at all like I thought it would. I thought it was going to be a triumphant chronicling of how I was victorious in my stoic challenge. But it didn’t turn out that way – at least for now. Today I feel low and overwhelmed. The stoics would probably chastise me for feeling negative emotions when I don't need to. And they are right. But I can't help my sensitive heart that feeling things sometimes too deeply.  And tomorrow is another day. Every day, even or sometimes especially the hard ones, are an opportunity to learn; to get one percent better. As I contemplate my temporary failure I realize how much I learned from the experience. Failing has made me a better leader than if I’d gone into the gym the very next day and with my lovely (vegan thank you very much) boxing gloves and punched the heck out of that punching bag. Not succeeding (temporarily) at my stoic challenge made me more empathetic to others facing their own challenges. And maybe in telling you about my struggles today it’s helped you feel safe to talk about your own challenges with those around you. I certainly hope so. Because you know what? We can do hard things. And make no mistake, there is a "we" and we are in this together. Now I’m off to change out of my sweatpants and clean my flat!

References:

Clear, J. (2018) Atomic Habits. London: Cornerstone.

Doyle, G. (2020). Untamed: Stop Pleasing, Start Living. London: Ebury Publishing.

Holiday, R. (2015) Obstacle is the Way: The Ancient Art of Turning Adversity into Advantage. London: Profile Books.  

Irvine, W.B. (2021) The Stoic challenge: A Philosopher’s Guide to Becoming Tougher, Calmer, and More Resilient. London: W.W. Norton & Co.

Magness, S. (2022). Do Hard Things: Why We Get Resilience Wrong and the Surprising Science of Real Toughness. London: HarperOne.

Rock, D. (2021). How to Convince Yourself to Do Hard Things. Harvard Business Review [online] Available at: https://hbr.org/2021/12/how-to-convince-yourself-to-do-hard-things.

Erin Roberts is the founder of the Climate Leadership Initiative. She endeavors to get one percent better every day. One of the ways she does this is by doing hard things on purpose which she sometimes does successfully and often fails at but always learns from.