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Lessons from an Application + Tips from Winston Churchill

“Mostly it is loss which teaches us about the worth of things.”

Arthur Schopenhauer (Parerga and Paralipomena)

My girlfriend recently emailed me a potential dream job that she thought I was the perfect fit for. I was elated to discover that renown author and habit-guru, James Clear, is hiring a podcast writer/researcher and producer. Given my nerdy passion for self-improvement and audio engineering, I figured this would be a fantastic opportunity to pursue.

I’ve always hated applications, but this one has taught me a few lessons that I think are worth sharing. Some came from the application itself, others came from my overachieving spirit taking on unnecessary challenges.

Future Opportunities are Difficult to Imagine

A part of the application that made me think was when Clear asked the applicant how much money they expect to be paid for the position. I know I’m fairly new to the “real world,” so to speak, but the idea of getting handed a blank check to do meaningful and potentially life changing work is so beautiful to me.

How crazy is it that there’s this job that appeared over the recent years that has no established monetary value. Then I got to thinking…how many other unforeseen opportunities are coming? How many other jobs will come that will give people the opportunity to write their own checks? It’s so wild to think about the seemingly boundless opportunities that come with our rapid technological growth. Podcast writer/researcher/producer was not a popular job just a few short years ago, but now there are people who will pay handsomely for someone with those unique set of skills.

After seeing this, I see that it’s so important to focus on developing skills that interest us because future opportunities are difficult to imagine and perhaps one day a well-paying and flexible job will look for someone with those particular set of skills in that particular combination. In a world of niches and specialization, we need to find new ways to make ourselves relevant and it seems like cultivating our inclinations is our best bet.

Modes of Growth

When I looked at my website, my writing, and resume, I was unsatisfied and embarrassed. I was so frustrated because I felt burnout creeping in and I couldn’t see any ways to make my situation better. I took a step back and saw this as an opportunity to level up everything, so even if I don’t get the job, the energy dedicated to this application is worthwhile. I had to stop with experimenting and work on presenting. Off with Experimentation Mode and on with Presentation Mode.

Once I switched gears, I was working harder than ever before. Suddenly, I knew what had to be done and saw multiple ways to get to where I needed to go. This was an important realization in a time of burnout and complacency. Once I switched my mode of growth, I had a whole new set of problems to tackle. I was so inspired that I made plans that will take way longer than the application window to complete, but that’s totally fine.

Being the nerd I am, I started to wonder why I had this newfound energy. I wanted to know what exactly broke me out of my burnout and complacency. I was thinking about Big Sean and when he goes into “Album Mode,” he’s focused, setting his intentions, attentions, and energy all in one place. That got me thinking…we all have different modes to our outward development. We don’t necessarily have to have “Album Mode” or “Presenting Mode,” but having different creative “modes” helps us switch to the perspectives we need to take action.

Paying Attention Paid Off

I kept stopping the application to work on the musical pillar of my online city and realized that I kept wanting to dedicate my energy to myself and my own endeavors. I’m not saying I’ll be James Clear, but James had to dedicate a huge amount of energy in order to create the body of work he has today.

If I’m naturally gravitating towards working on my own endeavors, then I ought to get out of my own way. For a while I wondered if I was paying proper attention to my own patterns and behaviors, but now I have another example as to why paying attention to our own behavior is worthwhile. When I made the switch from working on someone else’s plan, to working on my own, I felt less anxious and stressed. The application didn’t cause me a huge amount of stress, but it does feel a hell of a lot better to work on my own contribution to humanity.

In the end, I decided not to submit an application but the lessons I got from it felt like a good trade.

-Future opportunities are difficult to imagine, so focus on what keeps you interested and useful.

-Have different modes of growth to help change perspectives in times of burnout or complacency.

-Pay attention to what I’m subconsciously trying to do and get out of my own way if it aligns with my values.

How to Be a Better Leader: Tips from Winston Churchill

One of the questions on the application was asking us how we would handle writing a practice podcast transcript on the topic “How to Be a Better Leader: Tips from Winston Churchill.” I thought this was an excellent question to ask because it gave Clear a clear idea (no pun intended) of how this new hiree will work once everything is said and done.

When I read The 4-Hour Workweek (which is on my Must Read List), Tim suggested to have a preliminary task set up for potential hires to see how each person would work. This way you can evaluate their workflow, how quickly they can complete the project, a sample of their work, and if you like working with them in general.

Given how I saw the question, I figured the best thing to do would be to actually write out the transcript and detail my workflow. Since I decided to not follow through with the application, I didn’t finish writing the transcript, but I did do a good amount of research for it and learned some valuable lessons. Without further adieu (in a much more casual manner) here are some lessons I learned from Winston Churchill on how to be a better leader.

Never ever stop.

“If you’re going through Hell, keep going.”

Winston Churchill (1874-1965)

I’ll start with one of his most popular quotes. Churchill was no stranger to situations akin to Hell. He participated in many wars as a soldier and a Prime Minister. War can be seen as close to Hell as we can get and Churchill had experience with it on the front lines as well as being in charge of millions of lives. On top of that, the guy lived to the ripe ol’ age of 90! If you’ve read some of my other posts, you know that I truly believe life is suffering and to reject that suffering is to reject life itself, so we must do everything we can to learn how to deal with that and other tragedies of life. I talk a little bit about this in my post Proclivity for Comfort. Since Churchill lived for so long, it’s safe to assume that the man has seen the innate hardships of life, which I believe can also be akin to Hell. I believe it’s safe to say that Churchill knows Hell and how to get through it. Keep going. If things get hard, keep going. If things aren’t hard, they will be. Plan for the worst and keep going.

On a slightly different note, I was also reading Austin Kleon’s third book, Keep Going, which is a solid book on how to stay creative in good times and bad. I’m pretty sure Kleon didn’t reference Churchill, but I want I mention this too since this week’s post is more about lessons I’ve learned over the last week. Kleon offers many different ways to stay creative, but the most influential idea for me was to make gifts. Basically, when you’re in a creative slump, make gifts to get in touch with your gift. When you think of creating something of value for another person, we see tons of new ways to utilize our talents.

Persistence will conquer strength, intelligence, talent and hard work. Without persistence, we are nothing. Being strong, smart, and talented can give us a leg up, but someone with more persistence will be the champion.

I feel like Churchill’s advice to keep going is amazingly perfect and simple, but to take it a step further, we should look for specific methods to keep going. Persistence is the goal, finding the methods to get there is our task. Excellent for leadership, excellent for conducting ourselves powerfully in the world.

Intentionality is for the strong.

“I like things to happen, and if they don’t happen, I like to make them happen.”

Winston Churchill (1874-1965)

Churchill has so many quotes, but a common thread between a lot of them is his reverence for intentionality. In a phrase, Churchill believed that people want things to happen, but don’t try to make them happen. He wanted to participate in life, not just observe it. He suggests that great leaders will bring out what they want into the world despite other forces working against them. The good leader delivers results, on purpose.

What comes with intentionality is confidence. When someone knows themselves as someone who can bring about their own will into the world, then they are confident, especially in times of uncertainty. Leaders view themselves as being able to impose their will on the world and NOT the other way around. Leaders have an Internal Locus of Control. Now, this isn’t to say that we should just do whatever we please and force others to act how we’d like, this is simple a mindset to approach potential problems from. When we are intentional, we build confidence, and when we’re confidence, we build intentionality. The combination of these traits gives us a backbone, and are way less likely to fold under pressure.

Pick your battles.

“You will never get to the end of the journey if you stop to shy a stone at every dog that barks.”

Winston Churchill (1874-1965)

This is similar to intentionality, because fighting every battle you come across, or stopping to shy a stone at every dog that barks, is not intentional at all. Getting distracted by ever disturbance you’ll come across will eventually stop you completely. Some things are worth ignoring or letting go. A good leader knows when to move on. A good leader knows when to quit. However, when the time does come for a fight a good leader must know how to conduct himself in battle, be it physical, verbal, or mental. We can’t give our attention to the barking dogs, for they are just beats who follow their lowly urges. These animals cannot see what we see and therefore their judgment cannot be taken into consideration. Haters gon hate.

Move beyond the failure.

“Success consists of going from failure to failure without loss of enthusiasm.”

Winston Churchill (1874-1965)

Churchill was big on failing early and failing often. I’m not surprised because Churchill was a smart guy. I talk about The Power of Failure a lot because it is the basis for learning. Churchill, without all the modern research on learning, understood that you have to be willing to fail again and again in order to achieve something of significance.

There is no other way to heaven except through death. We must be willing to sacrifice the part of ourselves that is wrong and inadequate in order to make room for the part of ourselves that is correct and competent. Learning that we’re wrong hurts and leads to suffering, but if we can willingly confront that part of our lives then we can fasttrack our abilities to learn and develop skills. Fail all the time, but don’t let it take you down. Excellent leaders are so because they have learned how to be.

We are never done.

“Success is not final, failure is not fatal; it is the courage to continue that counts.”

Winston Churchill (1874-1965)

This also ties into never ever stopping. Persistence is what will bring us to the promiseland, so to speak, but what comes with persistence is the assumption that there is more that lies ahead.

It makes sense that Churchill thought this way, given the events that he lived through. He saw the end of WWI, the war to end all wars, just to see the beginning of WWII. He saw the futility in trying to end the problem of problems. Our success are only successes for now. Our failures are only failures for now. He understood what matters in the face of this absurdity, to develop ourselves to have the courage to continue.

This fascinated me for a while. I couldn’t understand why someone would not want to try to solve the meta-problem (that problems exist) and would rather focus their energy in building the courage to keep fighting, but then it hit me. Success, fulfillment, the peak human experience is not defined by what we are aiming in the earthly sense. Aiming at”worldly” outcomes yields a temporary release, but aiming at virtues gives us a whole new set of skills. Churchill switches the conversation from aiming towards vaguely defined earthly success to aiming towards the virtues. This gives us the ability to contend with existence with a whole new, and more effective, arsenal. Success is a journey. Whether we failed or succeeded yesterday, it doesn’t matter. The truth is, we must do it again today.