The Entrepreneur and the Art of Letting Go

by | Apr 28, 2021 | Entrepreneurship, Leadership

Delegation is a tricky business. We know that we need to do it and that we can go farther with the help of others. And yet, many of us refuse to delegate. Or we do it so poorly that we eventually end up taking back the reins. Here are just a few ways we tend to mess up delegation:

  • We don’t set clear expectations, so the employee thinks they’re doing great while we think they’re slacking.
  • We don’t understand the tasks we hand off, making following up on progress a challenge.
  • We don’t think anyone else can learn a task, so we hold on to it or take it back the first time someone asks a question.
  • We hover and nitpick, making others uncomfortable and ignoring the possibility that someone could offer improvements on our processes.
  • Similarly, we check and double check every stage of the process, slowing down progress and creating more work.
  • We don’t model productive delegation techniques to employees or train them to do it well, creating a second generation of bad delegators.

It is a vicious cycle. If you don’t learn to become a master delegator—and pass those skills on to your employees—you won’t grow your business as quickly as you should. Thus, let’s start at step #1 of learning to let go by figuring out what to take off your plate.

If your days are anything like the one I described earlier, full of interruptions and emergencies, then knowing what you can take off your plate will be tough, because your actual day likely looks nothing like what’s on your calendar. It’s hard to get a read on the full scope of things you do without an accurate record.

If that’s the case, start keeping a notebook. On one side of the page, write down a list at the start of each day of all the things you think will be most impactful to accomplish that day. On the other, write down everything that you actually do. Update it several times a day to make sure you’re capturing everything accurately. Here’s what mine might look like:


  • Review budget for next quarter
  • Book flights for upcoming trips
  • Prep for board meeting
  • Write 1,000 words for my book
  • Find location for company outing
  • Make it home at a reasonable hour for dinner


  • Called into meeting to clarify goals
  • Responded to a customer email
  • Took a phone call from a mentor
  • Started researching locations for company outing but got distracted by ordering lunch
  • Wrote 250 words for the book
  • Got home at 8:00 p.m.

There is a lot to be learned from this exercise. Some of the things you weren’t planning for might actually be important and need to be factored into your future to-do lists. Some things on your to-do list might fall into a similar category and could be easily handed off to someone else.

You only have so much time in a day, and that time is valuable. So, while this exercise will also take some time, it’s the first step to taking control of your schedule. Writing it down gives you a way to quickly reference what is getting done, what’s not, and what really should be. And when you’re able to see tasks like “prepare for board meeting” being passed by for ones like “order food for company picnic,” letting go will become a whole lot easier.

It takes some time to get a read on how much you can realistically take on in a day and which tasks you should delegate. But once you get the lay of the land, your time will be spent on things that can make a difference in your company.