Embracing Radical Candor to Overcome Your Worst Habits at Work

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Last month, while I was on a cross country flight, I read Ray Dalio’s seminal document, Principles, for the second time this year. For those of you who don’t know Ray, he is the Founder of Bridgewater Associates, the world’s largest and arguably most successful hedge fund. Ray runs Bridgewater according to principles that he has developed over his 40+ year career. Some would suggest his approach and views of the world are radical but it’s hard to argue with Bridgewater’s success. Ray is a big proponent of radical transparency in order to arrive at the truth. His principles include embracing failure, being in synch, building teams carefully, and running an organization like a machine. While I don’t share all of Ray’s views, I do believe that just about every organization imaginable would dramatically improve if they read and adopted even half of the principles.

After I finished reading the document, I began to reflect on my own values and principles. I also began to question my own effectiveness as an investor and as an employee in the spirit of radical candor. What am I good at? What drives me? What are my blind spots? What are my bad habits? Where am I falling short? What am I currently struggling with? By asking myself these questions and investing the time to reflect, I was able to shed light on some of the areas at work that I should focus on. This process was both cathartic and enlightening. What I found was surprising and incredibly transformative but it required a structured process and heavy doses of reflection and self inquiry.

Several weeks ago, I developed a process to identify my poor work habits, understand the underlying causes and then create a plan to redesign how I respond to situations, make decisions and spend my time. The spirit of this exercise was simple: to drive more productivity, to try to understand myself better and ultimately gain a greater peace of mind. Here are the steps I took to change some of my least productive and most limiting behaviors on the job:

  1. Identify the fears that impact my work
  2. Note my big struggles and then tie them back to my fears
  3. List all my bad habits that contribute to my struggles and feed my fears
  4. Brainstorm practical solutions to ‘cure’ each bad habit
  5. Ranked the list of cures based on priority, impact and pain
  6. Implement a plan to fix three to five of my worst habits
  7. Measure my progress monthly and reevaluate the list

Keep in mind this is not a once size fits all approach and it’s certainly not scientifically proven. I simply developed a process that I believed would work for me. It’s important to note that a) I devoted at least an hour to each step, b) I removed all distractions during each session such as shutting off my phone, and c) I sequestered myself at the library so I could intensely reflect and focus without any interruptions at home and work. I found journaling for steps 1–4 helped me let down my guard and channel inner candor and creativity.

I’m amazed how much I learned about myself in these short sessions over the last few weeks. I essentially put a magnifying glass on my fears, struggles and worst habits that have been causing mental friction and seriously limiting my productivity. The process so far has been both illuminating and liberating. Here is a peek into my exploration and some of the things I discovered.

Fears: After two hours of reflection and brainstorming, I generated a list of six primary fears that effect me at work and force me to react. It turns out that I have a fear of people not liking me so at times I try to please people even when it’s not in my best interest or what I feel like doing. Like many other investors, I also suffer from FOMO (fear of missing out) in certain situations. I’m also petrified of failing and not delivering results which is why I tend to overwork. These are just some of my fears but it should give you a sense of how honest I was throughout the process.

Struggles: Once I listed my fears, I was able to reflect on the high-level problems that I cause for myself. These are the areas where I feel the most pain or a drain on my productivity. At the end of the exercise, I identified six big struggles which include saying yes too much, being a slave to my calendar and email, and not maximizing every minute. This exercise set the stage for me to identify the underlying habits that were causing these overarching problems.

Bad Habits: I carved out three hours during a long trip to brainstorm which habits have been holding me back. I identified these habits by reflecting on my struggles and asking myself the following questions. Where do you feel the most pain on a daily basis? Which problems are self inflicted but within your control? What activities are limiting your work quality and output? The list was fairly comprehensive. By the time I finished, I identified and categorized thirty five habits. Each of these ultimately tied back to my struggles and then to my fears. One worth noting is daily breakfast meetings rather than going to the office early. These breakfasts can be a huge drain and distraction because I often won’t accomplish much until the late morning. Another negative habit I’ve developed is reacting to email based LIFO (last in first out) rather than prioritizing based on sensitivity. Many of the these limiting behaviors centered around communication, time management, goal setting and prioritization.

Cures: Once I identified the roadblocks to productivity and peace of mind, I generated at least two cures for each habit. For breakfast meetings, I have decided to avoid them at all costs with very rare exceptions. For reacting to email, I created a detailed prioritization system. For example, I now to respond to portfolio companies, any fire drills or my partners before anything else. By cataloging practical and immediately actionable remedies, I’m able to attack my deep rooted fears while also changing how I approach work. This section alone could be a separate blog post.

Implementation: Here’s where the rubber meets the road and the real change happens. I took the list of my habits and fixes, and then ranked each of them based on priority, pain and impact. Remember, my criteria will likely different than yours so I’d encourage you to focus on what you’d like to optimize and change. Once I developed my ranking, I immediately focused on the top five most limiting habits. My is goal to attack five over the course of a month and then move down the list every thirty days. If I’m able to overcome even half of the list then I’ll dramatically improve my output and mental state.

Re-evaluate: The final step will be to measure my progress on a weekly and monthly basis. I’m not quite there yet since I’m only a few weeks into the exercise, but I’ve taken some steps to ensure I stay focused. For example, I’ve blocked out 15-30 min each Friday to assess my progress and to review the list of cures so they remain fresh in my mind. I’m still working on the first batch so time will tell how much progress I’m able to make before the end of the year.

As you can probably tell, this exploration requires a significant time commitment, ruthless honesty and a strong desire to improve. I also found it requires a healthy dose of humility and maturity. But so far the process and the results have been well worth the time and emotional investment. While I’m not even a month into this experiment, I’m already seeing huge results and developing a better understanding of who I am. Looking in the mirror and acknowledging my flaws certainly hasn’t been easy, but I’d much rather shine light on them so I can grow and improve as an investor, partner and husband. To me, that’s much more exciting than pretending I’m flawless.

How do you change your worst habits at work?

The Author

A mindful VC in NYC

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