My Relationship To Failure & Trying to Turn the Tide

This year has been hard. Maybe you can relate. I’m becoming ever-aware of the chasm between what people see and how I actually feel about myself. At times it’s so wide that I believe I’ve fooled people for years. It’s hard to know how to convey the times where I feel I am falling short of what I’m supposed to be.

I recognize that feelings aren’t always easy to trace, they are non-linear. And don’t get me wrong I’m still experiencing triumphs and mountaintop highs. I just feel that ‘we’ as in the world are getting worse at sharing lows and being real about where success actually comes from. The past few months I’ve learned a lot about myself . So I’ll try to convey some takeaways below.

Failures have a direct correlation to your success and your ability to experience gratitude for successes.

When I was 18, I was dead set on living abroad. In two weeks time I put together a plan to move to New Zealand, raised money and went. One week in I got homesick and went home. It was embarrassing, devastating and brought about shame I hadn’t felt before. Years later I gave going abroad another chance and have now lived abroad for 11 years. The failure I experienced made me take pride in something as simple as coping with living abroad and later thriving abroad.

I failed miserably at speaking when I was 22. For two years I avoided speaking publicly. Years later when I got into the eCommerce world I reluctantly took on speaking publicly and worked incredibly hard to do it well. I’m not a great public speaker but what I can say is that when I speak publicly it means a ton to me because of the fear attached to my failure. People talk about conquering fears and perhaps this can happen but I think for some they can come rearing their ugly heads once again.

This year has brought about new types of failures and new realizations. I led an incredibly talented team of people around the world. We went through big changes and I put some of them in positions where they didn’t feel sure, they didn’t have clarity and I wasn’t in tune enough to pick up on how these changes impacted them. Things reached a head at the worst possible time. On my 18 hour journey home I sat 40k feet in the air thinking about what happened. It was sobering, it’s humbling and it gave me time to be honest with myself. Knowing where you stand and being confronted with truth is a gift. Being knocked down brought me to a place where I felt like I almost had a blank canvas to work from. It wasn’t an easy road to confront how I could be better but when all you can do is focus on getting better it’s not a bad spot to be in. Embrace these moments. Don’t blame and don’t dwell on what went wrong. Do confront who you are and work on things you know you need to improve.

Take control of past, present and future

We can give ourselves too much credit. We can sell ourselves short. I’ve learned that I almost always am too hard on myself when it comes to failure. I either dwell on things in the past or I spend so much time worrying about things I can’t control in the present or future. One thing that’s helping me now is separating what I can control and take action on versus what I can’t change. Sounds simple right? Make a deal with yourself. If something is bothering you give yourself 24 hours to do something about it and everything that is out of your control don’t give it your thoughts (time). And remember we really do grow the most through challenging times, this gives me a lot of hope.

Making assumptions about what’s driving others.

A massive pitfall for me is reading into actions too much. It’s especially easy to do this when you work with a distributed team or interact with people on the internet. I often let things people say or don’t say lead me to think things about them that are not fair. Dwelling on these assumptions is like opening pandora’s box of emotions. Through some coaching I learned not to jump to assumptions about what people intended. This is something I’ve always struggled with. It’s not easy but try to assume the best of people and always give people a chance to account for their actions. Don’t let your assumptions of people’s actions drive you to a negative place. For me this means trying to immediately put things behind me. Aim to spend less and less time analyzing other people’s intentions. If you have questions or issues that aren’t resolving than have an honest discussion even if it will be awkward.

Comparing is dangerous.

In the world of twitter, facebook and instagram it’s really easy to see all the things I’m not. And to see the things that others are. Perhaps I’ve contributed to this problem in a lot of ways. Global travel, exclusive tech posts and carefully curated photos. How can we stack up? In many ways I’m finding it harder and harder to post anything unless it’s perfect. This is especially true with writing. I love writing but I have this massive growing inferiority complex about sharing. It’s dangerous because I’m triggered by being liked, loved and retweeted. I want to work towards a more honest aim with myself and digital self. I’m not sure how easy it is to be authentic in this space. I struggled to reconcile who I thought I was supposed to be for my job and who I actually was. This is exacerbated the bigger and/or cooler your company is perceived to be. All I can say here is that I desire to be more raw about the realities of my self and my world. My aim is to strive for meaningful sharing. So consider this my first step towards that.

Balancing being pragmatic and being honest. What are you actually feeling?

I’ve spent so much time being careful and practical about my career. This hasn’t always been the case. I left a great job in Southern California to work for a non-profit in South Africa when I was 23, with no long-term aim in mind. I use to take the approach that everything will work out. It wasn’t until I was 28 that I realized I needed a plan and I’ve been spending the past 6 years doing everything I could to be successful. It was really hard and it took about 6 months after this realization for me to get back on track.

But what happens when your success on paper doesn’t match up with how you are feeling? What happens when you’ve lost touch with what you are actually feeling? In a coaching session, I was confronted with this. I couldn’t place my feelings, I couldn’t reconcile a blanket statement of ‘feeling like a failure’ to an actual feeling until my coach walked me through 10 minutes of meditation. At the end of it, I could pluck the feeling out. I felt shame. Honestly, I’m still not sure what to do with that but what I do know is that I have to get better at an understanding of my triggers and dedicate more time to recognizing what I’m actually feeling. I also have to look at my life and make sure I’m placing the right value on the right things.

Self Care 

I’ve spent the last 3 years bouncing around. It’s been wonderful. I’ve learned so much about the world and myself. My journeys have taken me to places I never thought I’d go. I’ve also nearly forgotten how to have a routine. I think there is a bit of an art to this, so it’s not all negative. Working from random places and learning to be effective anywhere. But I’ve also realized the toll that traveling and being unsettled has had on me. At the end of 2017, we decided to move to Berlin from London. A big part of this move was to become more settled and invested in a place perhaps even a community. I felt like remote working was taking a toll on me and I needed more interaction and involvement. Due to a bunch of boring visa stuff we never really got to experience this but we will soon enough :).

The two biggest areas I need to improve on is making time to be still and making time to exercise. When I can hit both of those actions I’m often at my best. I’m also learning to avoid actions that are harmful to my well being. Things like checking slack when I wake up or in the evenings are super detrimental to my well being. Learning to know when to put work aside is so key to my happiness and my success at work.

Be gentle with yourself.

Be careful about the narratives you weave about yourself and those around you. Give yourself credit by reflecting on how you’ve overcome failures and grown. I hope my reflections encourage you to be true to who you are and where you are at. Understand that behind every massive success is a self-doubting person full of failures. My life is not my social feeds or fake smiles. I’m striving to be true to myself and re-discovering who I am and what I stand for. I hope you can do the same.


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