When to change paths vs. stick with the one you are on

3 mountains
3 mountains

On Saturday, I was supposed to run a marathon. 4 months ago, I put a date on the calendar and said that was the day I was going to run my first marathon and I would do so in under 4 hours.

The training had been exhilarating for me. I love challenging myself to do difficult things and using discipline and consistency to move toward my goal. Every workout, I showed up and stayed grounded in the process of getting a little better every day.

As I spoke about in my last reflection on running, 2 months into my training I injured my foot, likely from overuse. I saw a doctor and tried taking a week off, but the pain didn’t go away. I realized that this injury was going to take some time to heal and if I wanted to stay in shape for my race, I’d have to figure out another way to build up my cardio. …


Why I run and a mentality to stay grounded in the process

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I went on a long run last weekend as part of training for a marathon. This run marked the halfway point in my four-month training, and I was set to do a half-marathon at my race pace. The results of the race would serve as a barometer for my progress thus far, so I was definitely excited.

However, when I was about halfway done with the run I felt a sharp pain in my heel. I brushed it off and kept moving. Then a few seconds later, I felt that sharp pain again. Fuck.

I stopped running and sat down on a bench, trying to reason with myself about what was happening. I felt disappointed that I wasn’t able to meet my checkpoint, and watched other people jogging past me. I started to feel sorry for myself. What if I wasn’t going to be ready for my race? What if my injury was serious? …


Removing the worry of acting out of priority

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One of the simplest yet most important lessons I’ve learned from obsessing over productivity is to get the right things done. Working in order of priority is about 95% of the game, and if you can figure out how to execute on these priorities, you will go a long way. But for an extreme optimizer like myself, even if I am acting in priority, the fear that I might not be is a source of stress.

A good example of this is with my old workout routine. I had a high-level vision for what my strategy was: hit the gym almost every day and rotate between different exercises and muscle groups so I could get stronger. Because I’d developed a fair amount of discipline and working out had always been a habit of mine, I executed on the plan pretty well and was able to achieve what I wanted. But, even though in retrospect I did what I needed, I always found myself stressed that I was doing too much of a certain exercise, that I was taking too many rest days in a week, or that any given workout wasn’t the right one for that day. …


A mindset to stay on course when things go wrong

You are here
You are here

I’m a firm believer in momentum. When you knock those first dominoes over early in the day and get small wins, your results compound and that success leads to more success. This is why James Clear, author of Atomic Habits, preaches so much about establishing good habits and systems; the micro-decisions we make throughout our days have a large impact on the trajectory of our lives. For this reason, I’m always trying to execute on my habits and systems to ensure I’m acting in line with the person I want to be. This involves things like performing my morning routine, time-blocking, getting enough sleep, limiting distractions etc. …


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One of the big things I’ve learned over the past year on my personal development journey is the importance of reflecting on your systems to ensure what has worked for you in the past is still working now and if there are any opportunities for improvement to give them a try. This idea is very much intertwined with a concept I wrote about called Provisional Truths —I believe we are meant to seek out the best ways to optimize our lives, but inherent in this idea is that there isn’t necessarily one right answer. …


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It’s taken me a while to figure out exactly how I wanted to respond to what’s been happening across our country. Yes, I donated and I signed some petitions, but I felt like I wasn’t doing enough. I felt that by not truly educating myself and sharing my thoughts, I wasn’t really doing my part. So I decided to approach the topic of racism the same way I would approach any topic I wanted to learn more about. …


Seeing the bigger picture behind building startups

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A little context to start: My name’s Drake and I’m a recent graduate from Northwestern where I built and sold eo, a dockless bikesharing startup that generated 20,000 rides. As part of graduating from an entrepreneurship fellowship I was in, I was given the task of writing a letter to future fellows to share the advice I had for them. I wanted to pass along what I put together because it really embodies a lot of what I have learned and the principles I’ve developed through entrepreneurship and life.


The concrete benefits from putting pen to paper

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I wrote my first article on Medium a couple of summers ago sort of by accident.

I had this amazing experience from exploring the limits of my comfort zone, and I was opened up to the possibilities of personal development. The combination of pride about what I’d accomplished (challenging myself to skydive, freestyle rap, sing in front of strangers…) and having a boring day at my internship led me to start documenting the challenges and make a personal reflection of what I learned. When I started writing the article, I really had no plans to share it.


An analysis of Self-Worth, Success, and Purpose through The Alchemist

During these times, I’ve done a lot of self-reflection and one thing I became aware of is that most of my anxieties are attached to my desire to be successful. From digging a level deeper, these anxieties are attached to my desire to be worthy and special. The underlying reason I get so worried about the outcomes of my startup or my career is that I’m worried that if they fail or are mediocre, then that is a reflection of me. And if my achievements aren’t special, am I? Am I not leaving a dent in the world? …


Productivity doesn’t come from using the best software.

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As I’ve experimented and tweaked with the ways to get things done more efficiently and to stay on top of everything, I’ve learned that it’s all about the system. Your productivity system has to work like a machine: whenever there’s an input (a deadline, an event, etc), your system has to have a way of processing it so that everything stays running smoothly. Everything needs to work together and any tools you use need specific roles. (An amazing resource that basically created this type of thinking is GTD). Because I value simplicity, I only use two tools: TickTick for Task Tracking and Google Calendar for Time Tracking. …

About

Drake Weissman

Using Medium to process things I learn.

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