The Entrepreneur and the Art of Letting Go

The Entrepreneur and the Art of Letting Go

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.

Hire for Your Values, and You Won’t be Sorry

Hire for Your Values, and You Won’t be Sorry

When I was in college, I was lucky enough to spend a summer in Thailand. I saved all year for the trip and tried to keep my expenses to a minimum. Even so, I was shocked when it came time to get my clothes cleaned there. The woman who helped me washed all of my clothes by hand. In exchange for hours of work, she asked for only $2 and refused to take any more.

What struck me most of all was the joy she exuded. Here was someone I shared almost nothing in common with, completing a task I had done hundreds of times, using a method I hadn’t ever tried. Her method, the soap she used, and even her feelings toward the task were new to me. But the end result was the same. This experience has stayed with me. Anytime it’s suggested that there is a single right way to do something, I think of her.

This experience instilled in me a determination to hire based on values. If your interview process gets to the heart of the candidate’s values, you’ll be able to decide if you’ll enjoy working with them, because working toward a shared mission is much more meaningful in the long run than workplace banter about your favorite sports team.

And more importantly, those employees may show you that there’s another path toward your shared goal, something you may have missed out on in an echo chamber of friends with similar backgrounds and experiences.

At the end of the day, you should hire the person who will do the best job, but it’s easy to mistake your comfort with someone for competence. So, make sure that your hiring process involves a few interviewers if you can, and outline the values that are most important to the role before you start interviewing. And when you get together with the hiring team to discuss each candidate, make sure that you each push to bring the conversation back to those values. Don’t let words like “impressive” or “likeable” go unchallenged.

Internal biases are something we all have. I know in my own companies, we are not perfect. But we are striving for better. We don’t just want to beat the industry statistics. We want to create an environment where everyone feels comfortable and like they can express their ideas freely. In doing so, I know that we’ll be better off as a company and will benefit from the sharing of ideas and debate. But I also know that we’ll make a positive impact on every single employee in the building. And that’s something we should all care deeply about.

As the company leader, I am constantly amazed by my team. I have seen the triumphant things they have accomplished, and they remind me regularly of how much I don’t know. We all have a choice when starting a company—hire people just like us who will reinforce what we already believe, or hire people who share our values but introduce us to new ways of thinking.

There is not one correct way to do anything, but you may be tricked into believing there is, especially if no one tells you any differently.

Teaching Your Employees Time Management Skills Is More Important Than Ever

Teaching Your Employees Time Management Skills Is More Important Than Ever

The art of emphasizing time management in the workplace is not new.

But whereas it used to be that entrepreneurs and their managers could keep an eye on employees, which led the employees to be more responsible with their time, the shift to a remote workforce has upset the equation.

A recent study by Canadian academic Brad Aeon, a graduate researcher at John Molson School of Business, Aïda Faber of Université Laval in Quebec City, and Alexandra Panaccio, associate professor of management at John Molson, which analyzed time management literature derived from 158 separate studies spanning four decades, six continents, and involving more than 53,000 respondents, seemed to reinforce that notion.

“People have more leeway in deciding how to structure their own time, so it is up to them to manage their own time as well,” Aeon said. “If they are good at it, presumably they will have a better performance. And if they are not, they will have an even worse performance than they would have had 30 years ago, when they had more of their time managed for them.”

This is where I would recommend a couple things. First, consider a workshop over Zoom with a handful of employees at a time, which explores best practices. Second, explore embracing some of the software applications like Asana, which will help employees manage their priorities, or Slack, which will help them reduce clutter in their inbox.

Another way to move them in the right direction is to help the employees see the bigger picture when it comes to time management. The researchers above found a strong relationship between time management and overall well-being.

“Time management helps people feel better about their lives because it helps them schedule their day-to-day around their values and beliefs, giving them a feeling of self-accomplishment,” Aeon explains.

That correlation, though obvious, is worth restating. The business owner wins because their business is more efficient AND because he or she is creating loyalty in the workforce, which also benefits the company.

There is one caveat to all this: Be gentle.

As the world continues to struggle through the COVID-19 pandemic, resist the temptation to compare time management skills with supposedly more successful people. This could backfire, creating what Aeon calls “time management shaming.”

“You see these social media posts saying, ‘Yes, there’s a pandemic, but I learned a new language or I woke up at 5 a.m. and accomplished more in a few hours than you will all day,'” Aeon said. “It makes the rest of us feel bad and creates unrealistic standards as to what we can and cannot do with our time.”

Instead, focus on how we are all on the same team. Be willing to identify mistakes that you have made, and how you are determined to do better. Your employees will match that determination, and your business will be the better for it.

Don’t Let Fear Sabotage Your Startup’s Success

Don’t Let Fear Sabotage Your Startup’s Success

Fear makes us do some strange things. It can keep us from starting something new. It can stop us in our tracks. Or it can cause us to turn into Tasmanian Devils, trying to do everything we possibly can to fix the problem, and usually causing a lot more problems along the way.

When I see entrepreneurs engaging in all of the unhealthy behaviors we just talked about, it’s usually because they’re scared. They’ve staked everything on the success of their company, and they’re going to do everything in their power to make it work, no matter the sacrifices.

This is personal for me. When I stayed up all night to make sure one of my companies closed our round of funding, I was feeling a mixture of excitement and fear. I didn’t want anything to go wrong under any circumstances. And that fear drove me to sacrifice my sleep (and the next day’s productivity).

Fear can be sparked by just about anything. A top-performing employee quits. A customer gets angry. The internet goes down for a day. You name it. There will be challenges in your business that bring your specific fears to the surface.

And when that happens, the passion you feel for your company may start to turn into unhealthy obsession. The only thing to do in these instances is to call attention to the problem. If you’re conscious of how much you sleep, the foods you normally eat, and the way you like to organize your calendar, you’ll be able to quickly recognize the warning signs of fear. When your routine gets out of whack, it’s time for a reality check.

Admit to yourself what’s causing this fear. Write it down. Say it out loud. Do whatever you need to do to draw some attention to it.

And once you’ve done that, slow down.

I know it feels like if you stop working for a second, you’ll never fix the problem. You’ll never make up the time. But this is rarely ever true. Stop working, walk away from your computer, and figure out how to address the problem. Do you need help? Ask for it. Call a mentor or a family member, and talk through the issue. Do you need deep focus? Turn off your email, go somewhere quiet, and do it.

Ask yourself, “What is the most important thing I need to do to tackle this problem?” Then do that, and only that.

And when you’ve solved the problem and start to feel the fear subside, it’s time for a reset. Just like I instructed my leadership team after a retreat, you need to find a way to make up that time. The reason is that you have to break the pattern of unhealthy obsession. Your system needs a shock so that you don’t continue on in the same unproductive pattern.

Try going to bed at seven o’clock one night. Turn off your phone for a whole day. Don’t set an alarm one morning. Read for fun. Take a short vacation if you’re able to.

After a reset, you’ll be better able to get back into your routine of healthy eating, sleeping, and exercise, and take control of your time again. Keep to that routine, and you’ll find yourself more productive and, just as important, happier.

In sum, don’t ignore the fear that pushes you into unhealthy habits. Do face your fear head-on and reset.

The Power of Validation in the Workplace

The Power of Validation in the Workplace

We constantly underestimate the value of words to build up or tear down.

While this is certainly true in everyday life, it is especially true in the workplace. And it is one of the reasons why I, as a serial entrepreneur, embrace the idea of bringing my employees together at least once a week to talk about their successes. It is validating.

Last month, a recent study out of Ohio State University (OSU) supports this practice. And not just once a week, but on an ongoing basis. Telling your employees something as simple as “I understand why you feel that way” can reinforce both their initiative and confidence.

In quantifying the value of positive reinforcement, the OSU researchers asked participants to remember a real-life incident that made them angry. When researchers did not show support or understanding for the anger participants were describing, the storytellers showed declines in positive emotions, the researchers summarized. But when the researchers validated what the participants were saying, their positive emotions were protected and stayed the same.

Similarly, study participants reported dips in their overall mood as they recalled the anger-provoking event, and only those who were validated reported a recovery of mood back to their starting point.

This speaks to the value of focusing on protecting positivity, according to Jennifer Cheavens, senior author of the study and a professor of psychology at The Ohio State University.

“We have underestimated the power of positive emotions. We spend so much time thinking about how to remedy negative emotions, but we don’t spend much time thinking about helping people harness and nurture positive emotions,” Cheavens said.

“It’s really important to help people with their depression, anxiety, and fear, but it’s also important to help people tap into curiosity, love, flexibility, and optimism. People can feel sad and overwhelmed, and also hopeful and curious, in the same general time frame.”

The full study, which was published online in the Journal of Positive Psychology, uncovered findings that are relevant for all relationships, she added.

“When you process negative emotions, that negative affect gets turned on. But if someone validates you, it keeps your positive affect buffered. Validation protects people’s affect so they can stay curious in interpersonal interactions and in therapy. Adding validation … helps people feel understood, and when we feel understood we can receive feedback on how we also might change.”

The results of such a practice are a healthy and profitable workplace, something all entrepreneurs can aspire to.

Lead Your Company Like You Are Visiting the Grocery Store

Lead Your Company Like You Are Visiting the Grocery Store

One of the things I dislike most about moving to a new city is getting to know a new grocery store.

I like to move through the store quickly and methodically. My list is written in the order I’ll encounter those items as I walk through the store (veggies first, bakery second, etc.). And you can bet that if pasta isn’t on my list, you won’t find me browsing that aisle. At checkout, I organize my purchases by size and weight. The heavy stuff that the bagger will want to put on the bottom goes first, and soft things like tomatoes and peaches go last.

I don’t feel a compulsive need to shop this way. But as more constraints are put on my time, I find myself naturally seeking out efficiency all over the place—even in the grocery store. It feels good to get in and out of there in half the time it used to take me.

The same way of thinking can be applied to work. What can I do to get the most out of my day? How can I make the experience of work go more smoothly? How can I make sure I complete my most important tasks of the day?

Logic-Based Thinking

I call this concept “logic-based thinking.” It simply means thinking about what you want to accomplish each day and mapping out a logical way to get them done.

It’s a lot like walking through the grocery store, where you could easily get caught up in all the distractions around you, like tasting samples or rethinking your entire meal plan after coming across a particularly beautiful display of brussels sprouts. You could wander through the seasonal aisle and get a jump start buying Halloween candy, or go around helping everyone who can’t reach the top shelves. But if you did all that, you might never leave.

Things like this come up at work all the time. Emails claiming to need attention come through, and you respond. Someone pops in to ask a quick question and leaves 45 minutes later. A new idea is brought up, and you find yourself deep in a research rabbit hole in order to decide if something is worth pursuing.

Start With a Plan

One day, Jairek Robbins, an accomplished performance coach, spoke to the employees of one of my companies. He said, “What we tend to do is shoot an arrow and then go draw a target around it. Then we look at it and call ourselves a good shot.”

That’s exactly what we do when we approach work without a logical plan. We look at all the things we got done, all the fires we put out, and we pat ourselves on the back for a job well done. Meanwhile, all the things we said we would do remain untouched.

Growing a business requires a higher level of thought than that. It requires us to identify the most impactful things we can do each day, to find a way to do them, no matter what, and to delegate everything else.