Questions from Entrepreneurs

About 15+ years ago I started working, advising, and mentoring other entrepreneurs and startup founders. I was an early participant on Clarity.fm, a mentoring platform mainly for startups, although it’s expanded beyond tech and entrepreneurship over the years.

As of 10/23/24, I’ve had 666 calls with entrepreneurs, founders, product managers, designers, engineers, students, moms, dads, and tons of other people of all shapes and sizes. I enjoy it.

Many calls cover the typical founder challenges: finding product-market fit, raising capital, recruiting, corporate structure, equity/options, contracts, business development, UX/UI, SaaS, etc. But sometimes, I stumble upon an interesting person who asks more than that. They want to know “how I do it.” How do I prioritize? How do I manage my time? How do I track to-do’s? They want to know what my philosophical practices are that have led me to success as an entrepreneur.

To that end, one mentee asked me:

My biggest challenge in both personal growth and entrepreneurship is staying organized. I’m realizing that my success depends on connecting all the critical pieces — from plans and ideas to schedules and tasks — within a structured system that aligns with effective time management and project-task organization. How do I make everything accessible, connected, and organized in a way that lets me focus on the bigger picture without becoming overwhelmed?

Here was my response:

At my first job out of college, I met a guy who used a very rudimentary strategy to manage his workload. He would bring a graph-lined notebook (like this) to meetings and make little checkboxes with to-do items manually. I started doing that and continued for decades. I remember writing a blog post about it, but I can’t find it anymore. Anyway, the simplicity of this approach and the satisfaction of physically checking off items worked for me. There were much fewer “tools” for managing to-do’s at that time, but even as the to-do craze flowed in the early 2000s, I still found myself reverting to the paper to-do list even after trying tons of digital ones.

Around that time, I read a book called Getting Things Done by David Allen. The book was a huge bestseller and probably still is. It created a movement called GTM, from which tons of tools and systems have been built. I highly recommend reading that book. I’m sure even the Notion founders read and utilized thinking from Allen’s work.

One thing I found essential when managing my to-do list and prioritizing work is deciding what “NOT” to do vs. what needs to get done. In my experience, cutting things that are less important or moving them to lower on the list is probably the most effective way to prioritize.

Notion is my tool today. I now use that religiously, and my workspaces are pretty built out. But you only need one thing to optimize workflow: the “Database Table.” This is a table of data that uses the Notion database to store documents and metadata. It works like a spreadsheet, setting the columns, including status or whatever other dropdowns/filters you want, and has sorting, grouping, filtering, etc. But each row of data represents a project/initiative/task. Then, you can click on that and have a document where you dump all the information related to that specific thing. You can link to other related pages; this way, you can always find all the details you need. If you only had that one table with sub-pages like that, you could manage an entire business. You can expand from there as needed.

Finally, I’ll say the biggest detractor to productivity, and one that screws me every day, is context switching. For me, and probably you, it’s hard because I love stimulating my mind with different things throughout the day. I can’t just do 1 thing repeatedly. The problem is that when I switch from one thing to another, my productivity drops exponentially.

At my current career stage, I’m optimizing for life satisfaction over production velocity, so I’m ok with it. But when I was deep in startup mode, it was a killer, and I had to force myself to focus on 1 thing, the most important and impactful thing, until it was done or blocked, then move on. The more I did that, the more progress I would make in the business overall.