The Benefits of Connecting Your Ideas with Obsidian

Until a few weeks ago, my productivity system consisted of the following: Using TickTick for managing tasks, Google Calendar for managing time-blocking + events, and using Notion for everything else (logs, lists, projects etc). Don’t get me wrong, I created a really effective system for Getting Things Done, but it wasn’t until recently after reading a book called How to Take Smart Notes that I found the missing piece I didn’t know I needed: The Slip-Box.

The Slip-Box is a note-taking system built for connecting ideas rather than filing ideas. If you imagine a typical note-filing system, you have folders…


Why Believing in Your Ability to Design Your Life Matters

Recently when I was out running early in the morning, I passed by someone slowly walking on the trail by themselves. At first, this suprised me. When I picture somebody who wakes up early, I see someone grinding on a workout before their commute or cranking out a deep work session on a side hustle. Not just going for a walk.

But as I thought about it, I realized that I had a lot of respect for that person because they were actually embodying what I see to be one of the most powerful mindsets you can develop to harness…


Why It’s Important and How You Can Develop Self-Trust

When I was younger, I remember once being described by a friend as an ‘underachiever’. A comment that was probably given without too much thought or seriousness. But something that stuck with me for a while.

I didn’t think I was an underachiever but as I thought about it, I realized I didn’t have a lot I could lean on to really refute the claim. I had done some admirable things, but nothing too extraordinary. I always had big ambitions but wasn’t fully convinced I was capable of amazing things.

I’ve grown a lot since then and my impression of…


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…


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

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…


Removing the worry of acting out of priority

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…


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…


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. …


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

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.

Drake Weissman

Using Medium to process things I learn.

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