The Time Management Conundrum

We all want to do a million things, but no matter what, it just seems as though there are not enough hours in the day.

So how is it possible that we look around and see so many people doing so many things? Why do we always feel like no matter how much we do, we’ll always be behind? And what have those hyper-productive people figured out that we haven’t?

This article endeavours to answer these questions by addressing the core issues from both emotional and operational perspectives.


In tackling this side of the story, I’ll begin with a confession:

To some people, I am that hyper-productive person who is doing a million things at once. To myself though, I’m still behind.

I’m writing this post on a website I built by myself four months ago. On this website, you’ll also find the eBook I wrote three months ago, the Account Behaviour Formula I created two months ago (which won me the CS Innovator of the Year award one month ago), and a link to join a Customer Success community I launched at an event that I planned, executed, and hosted myself one week ago.

In addition to my Customer Success efforts, I also speak at—and run workshops for—startups and organizations around Toronto, I work full time at a startup, I support my partner’s artistic career, I regularly mentor recent graduates, I’m regularly mentored by brilliant and generous entrepreneurs, and I was on the founding team for the Venture Out Conference, for which I’m now a Strategic Advisor.

That’s my “work” life. I won’t get into my personal life, but I promise you I do have one.

The point I’m trying to make here is that I understand why people might look at me and think I’m hyper-productive, but it’s all a matter of perspective. I’m sure the people whom I admire for their productivity also feel how I do—that they could be doing more. This leads me to problem number one…

Problem: Our generation feels that we are always behind. We feel that we always need to be better, smarter, more talented, more accomplished, and that to take pride in our accomplishments is self-indulgent. We therefore downplay everything we do, both to ourselves and to others, which reinforces the idea that we are not doing well enough.

Cause: The internet (through social media) has created an environment where we are not only competing globally, but one where we only see what others want us to see: the best 5% of their lives. Meanwhile, we see the full 100% of our own lives, and compare the two as if they were somehow equal.

Potential Solution: Limit use of social media wherever possible, surround yourself with positive people who lift you up and support you, and while you keep pushing forward, stop occasionally to take a look behind you to appreciate how far you’ve come.


Before I can provide specific tips or advice on how to optimize your time management, I first have to ask you:

What is your reason for wanting to be productive?

If you don’t know, or your answer is something like “because people tell me it’s important,” then I’m sorry but this article will be useless. I’ll explain by addressing problem number two…

Problem: People don’t know what their purpose is. The essence of improvement is change, and change requires purpose. Every year, millions of books about getting rich and becoming happier are sold, yet 99.9% of people who read those books don’t see a measurable difference in either their wealth or their happiness.

Why not?

Because there’s no purpose behind their goals. “I want to get rich” and “I want to be happy” are simply abstract concepts that have no structure or achievable objectives. “I want to save $100,000 so that I can send my child to university” is a specific, achievable objective. “I want to have $1 million in the bank by the time I’m 40 so that I can retire early and travel with my partner” is a goal with a purpose. “I want to be a more positive person so that my children will grow up feeling happy and loved” is a goal with a purpose.

Cause: For almost 2000 years, the church and/or government dictated what was right, wrong, smart, dumb, good, bad, beautiful, and ugly. Over the past few decades, the decline of faith in the church, and trust in the government, have led to a rise in individualism, such that it is now up to each of us to make those judgements for ourselves. The trouble is, it’s hard work. You can spend weeks, months, even years thinking, writing, reflecting, and discussing with others to determine what “good,” “bad,” “beautiful, and “ugly” mean to you. Some people do choose this route, but most choose instead to let someone else dictate it for them.

“My parents think Conservatives are right and Liberals are wrong? Ok, that works for me too.”

“My friends think we should welcome more refugees to Canada? Sounds good to me.”

“Kim Kardashian is wearing purple lipstick? Wow, that’s so beautiful.”

And now we have established social markers for success and happiness (cars, property, sex, fame, etc.) that most just take for granted, instead of reflecting and thinking about why they might be chasing those things, and what happiness and success really mean to them as individuals.

Potential Solution: Take some time to reflect. Think about how you currently view the world and ask yourself “why?” Get in the habit of questioning what others tell you “success” or “happiness” may be and how to achieve them. Find your own purpose and start to follow your own path.

Now, I realize that this answer is quite conceptual, so I’ve also included below my top three strategies for optimizing your time and maximizing your productivity.

One: Make Lists.

Make lists for everything. My friend and mentor Erin Bury and I joke about the fact that we both put things like “eat lunch,” “brush teeth,” and “make bed” on our lists — things we would be doing regardless. But putting them on a list means we’ll get to cross them off that list, giving us a hit of dopamine each time, and allowing us to build momentum to cross off the more challenging things throughout the day.

I have lists for work, categorized by priority (i.e. “To do today,” “To do this week,” and “To do whenever”), I have lists for personal projects (i.e. “Blog ideas,” “Startup ideas,” “Events”), and I have lists for just getting things done. Below is an example of a general “to-do” list from a Sunday a few months back, when I was writing my eBook:

  • Wake up (yes, I even put that on my list)

  • Have breakfast (while watching Netflix)

  • Brush teeth

  • Write eBook section on churn management

  • Fold laundry (while watching Netflix)

  • Eat lunch

  • Brush teeth

  • Make bed

  • Go to Shoppers/Loblaws

  • Go to the gym

  • Shave

  • Shower

  • Watch Netflix (yes, I watch a lot of TV on Sundays)

  • Write eBook section on NPS

  • Make dinner

  • Chill with Anthony (my partner, who usually works on Sundays during the day)

  • Read before bed

Without a list, I could probably have done most of those things. But would I have thought about what order I would do them in? Would I have felt proud crossing off each item? Would I have ended the day knowing exactly what I had and hadn’t gotten done? Not at all.

Lists are also key for long-term planning. You want to put on an event in three months? Open a business? Take a trip? What are all the things you need to do before then? List them, and you’ll get them done.

Often, people get overwhelmed because they “have a million things to do, and not enough time.” “A million things” is an abstract concept, and not something that can be crossed off a list. In actuality, these people probably only have 10-20 things to do, and while some of these may have to happen that day, many can probably be spread over several days or weeks. Writing these things down turns the abstract into reality, and lets you breathe, plan, and execute, item by item.

Two: Log as much as you can in your calendar.

I’m still trying to get better at this, but I’ve seen that by consistently using one calendar for everything (phone calls, work meetings, going out with friends, etc.) I’m not only a better planner, but I experience less stress as well because I can look a day or a week ahead and see exactly what I’ll need to do on any given day.

Three: Prioritize and Purge.

There are so many people and things in life that will drain you. They’ll drain you of time, energy, and happiness, which are arguably the most valuable resources you have. That is why I believe that in order to increase your productivity you should first determine what your priorities are, and then purge any draining elements from your life, while maximizing the elements that energize you. My top two priorities right now are: Spend as much time as possible with my partner, and continue growing and nurturing my Customer Success community. A drain I removed a few months ago was Facebook. It’s not a coincidence that my productivity spiked shortly after deleting my Facebook account.

When I was feeling overwhelmingly busy about six months ago, Erin gave me some great advice. She told me that when something came up, before saying “yes” I should give it a score out of ten, and unless it was a nine or a ten, I should say “no.” This methodology has allowed me to be both happier and more productive, as I’ve been able to better tailor my time to my priorities.

I hope you have found this article helpful! I would like to conclude by sharing my own “why?” with you. The reason I strive to be productive and manage my time so efficiently is this:

There are so many amazing, wonderful, and exciting things that this world has to offer. I only have 90 years or so (knock on wood) to experience as many of those things as I can, and so the more efficient I can be with the time I have, the more experiences I’ll be able to pack into my remaining years. I know I won’t be able to do everything, but if I can look back on my deathbed and say “holy crap I did a lot of awesome shit” (in those words exactly) then I will count my life as successful.

Ben Winn