Life Strategies


The Hard Part About Leadership – The Final Part

If you missed Part I or Part II  on the hard part about leadership, you can find them at, in the meantime, here is part III.

Starting before you are ready – Successful people start before they feel ready, it’s hard because you are pulled by excitement and deterred by confusion simultaneously. If you’re working on something important, then you’ll never feel ready, but people are watching, they are waiting and no matter how long you wait you won’t be ready, so shoot the puck.

Sticking with a tough decision – It takes guts to make tough decisions, they are often misunderstood or vehemently opposed. What takes real guts is to stick with a tough decision, it’s one of the harder parts of leadership. We can’t ask for the right answer since there probably isn’t one. But when we learn how to develop a point of view, we are able to stick with a tough decision even during a storm. Don’t forget that emotion is the enemy when holding to tough decisions.

Leading From The Back – A leader’s job is to create more leaders, and there’s only one place this can be done from: the back. When we lead from the back, we are out of the spotlight, giving credit away, taking responsibility but not stealing the revelation someone makes, and understanding every decision we make is about people.

Dr. Isaiah Hankel, speaker and best selling author, shared the following with me recently. “It took me a long time to realize I was leading from the main stage, instead of stepping back and taking responsibility of all the mistakes in the organization. This was highly frustrating for me and my team, until one day I realized that no one on the team was taking responsibility for anything because I was not openly, and vocally stepping up to take responsibility myself.  This meant saying, ‘This is my fault because I didn’t give you enough guidance’ and, ‘Here’s what I did wrong.’ I then moved to the back and let others take the spotlight and simply guided from the sidelines.”

It’s extremely hard to lead from the back because we have so many images and stories where the hero is bigger than life, standing up front, on stage soaking it all in. But when you realize the monologue creates far less value than the dialogue you end up asking more questions. This on its own moves you to the back, where great leaders might not shine in the spotlight, but they create lasting and meaningful results.

Like most things in life, leadership doesn’t get easier. Leadership is necessary in all aspects of our life. Leadership is present in parenting, community, and it even impacts friendships. Being a humble and compassionate leader does not need to conflict with being a decisive, creative, and charismatic leader. Onward and upward.

Part 2 – The Hard Part About Leadership

Like most things in life, leadership doesn’t get easier and it’s present in all aspects of our life. This means, there are hard parts within leadership, but not to fear, once identified you embrace and leverage them.

Last week I wrote about Accepting there isn’t one answer (or one way), dealing with unexpected outcomes and being misunderstood. This week I want to cover four more.

Know your edges – You have a top and a bottom in your skill set and you have edges that are the boundaries of who you can be with these skills. These aren’t just how good you are at your job, or technical skills, but also your emotional intelligence and how you behave. A good example of your edges is your your ability to engage when under a lot of stress or your empathy. They are what they are, but knowing them, acknowledging them and working around them is the hard part.

Knowing who you are on your worst days and what you can accomplish on your best days creates a strong framework for an aware and emotionally intelligent leader. Knowing who you are on good and bad days allows you to be cognizant for when you hit an edge so you can fill gaps or step aside.

You are not the smartest person in the room – It’s often tough to admit you don’t have the answer, since after all, you are the leader. But a really important transformation happens when one not only admits they don’t know everything but actually ensures they are never the smartest person in the room. It’s an attitude and thankfully, one that can be learned!

Surrendering to conflict – Words like conflict have been labeled as negative, something that causes stress and should be avoided. The fact is though, that it’s impossible to avoid conflict, so why label it good or bad? Instead, embrace it. It’s hard because we often submit to conflict instead of surrendering to it.
Conflict solves problems, builds emotional intelligence, and allows for creativity to flourish. The hard part is not letting your ego get in the way.

Coming to grips with the fact you are not an imposter – You can’t make the voice go away, but you can come up with a better response. One of the tough parts about leadership and the corresponding success is thinking that it’s luck or a one-off. You find yourself having constant thoughts that you are a fraud and everyone will find out. When you get curious you discover an interesting thing, it’s a false voice, that only serves to knock you down.

Seth Godin says, it’s rampant (the imposter syndrome). The big reason is that we’re all impostors. You’re not imagining that you’re an impostor, it’s likely that you are one. Everyone who is doing important work is working on something that might not work. And it’s extremely likely that they’re also not the very best qualified person on the planet to be doing that work. How could it be any other way? The odds that a pure meritocracy chose you and you alone to inhabit your spot on the ladder is worthy of Dunning-Kruger status. You’ve been getting lucky breaks for a long time. We all have. Yes, you’re an imposter. So am I and so is everyone else. Superman still lives on Krypton and the rest of us are just doing our best. Isn’t doing your best all you can do? Dropping the narrative of the impostor isn’t arrogant, it’s merely a useful way to get your work done without giving into Resistance. Time spent fretting about our status as impostors is time away from dancing with our fear, from leading and from doing work that matters. The great part of this is that it’s only a voice and although you can’t make it go away, you can create a better response, such as “go fuck yourself, not only am I not an imposter, I’m a rock-star!”

The way I’ve dealt with the imposter syndrome is by acknowledging its voice, saying hello, and then goodbye. At its source, I recognize it comes from being uncomfortable with loneliness and the more I become excited about loneliness the better I get at focusing.

I’ll be back next week with the final three hard parts of leadership.


The Hard Part About Leadership

Things don’t get easier as you progress. That’s because as you progress, you move up, and as you move up the skills required are more challenging. If things get easier you’ve likely plateaued or even slipped a bit.

Like most things in life, leadership doesn’t get easier. Leadership is necessary in all aspects of our life. Leadership is present in parenting, community, and it even impacts friendships. Being a humble and compassionate leader does not need to conflict with being a decisive, creative, and charismatic leader. That’s just one of the hard parts about leadership.

When examined, these hard parts aren’t so much a thing to do but a way of being that starts with a big dose of self-awareness. These hard parts listed below can be humbling, but incredibly impactful on everyone around you.

Accept there isn’t one answer (or one way) – It’s often easy to find an answer, an initial solution. We are conditioned to accept an answer that solves our problem or addresses our question. We often stop at this point. Why keep searching when we’ve solved the problem?

The hard part revolves around understanding that even if you’ve found a way to launch or to fix a problem, you’re just starting to scratch the surface of possibilities. Understanding and accepting that there’s always going to be dozens of answers to the questions and ways to fix a problem is what separates good leaders from great leaders. It’s easy to go with an answer that first solves the problem, it’s hard to admit that there are definitely more answers and more work ahead until the best one is found.

Dealing with unexpected outcomes – Making quick and efficient decisions is a fantastic skill. Having the reflexes of a goalie helps to keep things moving. However, even if you have the moves of  Patrick Roy, you will lose if you hold onto your desired outcomes too tightly.

Having a vision of how you want things to turn out is OK, setting goals and targets is OK, but you can’t be attached to them. There’s a simple reason why. If Vegas put odds out against the likelihood of you being exactly right they’d be somewhere around 1,000:1. The reality is that we make decisions and from that decision comes an outcome and it’s rarely exactly what was expected. In fact, outcomes will often be totally unexpected.

The hard part is dealing with the unexpected outcomes if you have married yourself to a certain outcome already. It’s easier on you when you accept whatever outcome you find yourself in. Disappointment becomes a thing of the past because you simply move back into the decision making stage.

Steven Sisler of the Behavioural Resource Group explains, “Not every brain type excels with the challenge of dealing with unexpected outcomes. Those who are more emotionally flexible have a higher capacity to accept whatever circumstances they find themselves in.”

He continues, “Greater flexibility comes from a more intense anger emotion coupled with a very low intensity within the patience emotion. The patience emotion relies heavily on “safer” and more “secure” environments. This is known as Preserving. Individuals who sport a Preserving orientation believe that all good things can only be received from an outside source and will automatically come to those who wait. The source is supposed to be safe, expected, and deliberate; problems and challenges are avoided at any cost. Unexpected outcomes are far more disruptive to this way of thinking because the brain sees it as an intrusion on their “preservation” land. In other words, you need permission to do anything outside of a what is already expected when on protected land.”

In my experience, it’s easy to articulate: don’t hold onto what I believe the outcome is going to be. In practice it’s one of the hardest parts of leadership.

Being misunderstood – No one likes the feeling of being misunderstood, but the best of the best must be willing to be misunderstood for long periods of time. The fact is that leadership involves a great deal of risk taking and thinking well into the future and not everyone is going to be comfortable with that. Simply put, there will be many who don’t understand your thinking. In fact there will be many who are opposed to your ideas. Being misunderstood slows down the weak while it empowers the brilliant.

Trust is the key to working quickly through misunderstanding. If people trust you, they’ll still support you. So in order to be effective and not always misunderstood, you need to build trust with everyone around you. This can start with simple things like always doing what you say you are going to do, having people’s back, and continually recognizing people for the small things. So, understand, and have no doubt, in order to make being misunderstood a little bit less hard on you, build trust each and every day.

I’ll be back next week with four more hard parts about leadership, in the meantime please feel free to leave a comment below.

Stop Investing In Your Weaknesses

It’s January 13th and already 80% of new year’s resolutions are falling short. People are trying to improve a weakness, others are attempting to correct misalignments in their personality, and some are working to develop new skills.

Maybe it was a boss who suggested the area for improvement or a boyfriend casually dropping the idea to join Toastmasters.

But why all this energy on a weakness?

We are trained from any early age to get better at things we are weak at, and it stays with us for a lifetime. Strengthen where you are weak. We don’t know any better, our brain has been imprinted with this rule and like a loyal soldier it stands on guard.

But imagine what would happen if you made small, incremental, even microscopic improvements each month on your greatest strengths. If you are an all-star front end developer, would a 1% improvement in your skills result in a greater gain than 10% improvement in your cross-team collaboration – something you’d consider a weakness? I can’t say for sure, but I’d suggest you examine it.

I’m creative, I develop unique products and highly engaging marketing. I’m really strong in this area. When it comes to logistics and back-end operations, I’m not weak, but I’m certainly not strong. I’m quite confident a 3-5% increase in my creativity and marketing tool kit would have a far larger impact than a 25% increase in my back-end skill set.  

I believe we focus on improvements in our weaknesses because subconsciously we are afraid of our own success and how powerful we can become. Society encourages us to improve where we are weak, but rarely inspires us to forget our weaknesses and put greater effort into incremental improvements in our strengths.

Efficiency means turning the crank right. Effectiveness is turning the right crank. A strength means you are turning the right crank, you’ve got that figured out, but why go and try to find another crank to turn? Instead, get that crank operating at a level that will bring you far greater satisfaction and far greater results than choosing a new area to improve on.

What’s your greatest strength?

What would a 5% improvement in this strength result in? Seriously, think about that.

Are you willing to focus 100% on improving your strengths a little each month?


What You Miss When You Are An Average Listener

I’ve been guilty of something that drives me crazy when other people do it. It’s not paying attention enough when others are communicating, not being fully present when I’m in a learning environment, and not being able to focus on one activity without multitasking.

Last year I drew this diagram to demonstrate to myself just how much I was most likely missing.

So I set out to change since it was not acceptable to me to waste time and energy on being distracted and missing out on what others were communicating and on what I was endeavouring to learn.

Here’s what happens when you improve your ability to concentrate.

More connections to the communication.

More opportunities to better understand what someone is feeling.

More chances to improve your knowledge.

Easy to draw, easy to understand, challenging to execute. Here are three easy ways to start moving the dial 1% at a time.

Concentration is like any skill, practice in error, perfect in error. Getting good at concentration is also like any physical training, you need to practice regularly using a series of methods. If you want to run a marathon you don’t just train by running, you leverage weight training, the quality of your sleep, and your nutrition. The same goes with becoming more present and becoming a better listener, you train using a host of exercises.

1. 10 minutes of meditation a day. Meditation is not about closing your eyes and trying to think of nothing, it’s about working the concentration muscle. You can have a major impact on your ability to concentrate on anything in your life by spending 10 minutes a day sitting still and focusing on your breath. Every time a thought comes into your mind, you bring yourself back to your breath. Some days will be easier than others, but the result is the same, you are strengthening your ability to concentrate in all areas of your life through meditation.

2. This one is not easy, but the power technology has over us is incredible. There are literally hundreds of thousands of people employed by all the big tech companies to ensure you are addicted to your phone and their apps. It’s not news to any of us that our phones are the most distracting thing in our lives. We are checking our email at stop lights, we are checking messages when we go to the bathroom and we bring our phones to the dining room table and sleep with them next to our bed.

So start small and work up from there.

Step 1: No phones at the dining room table while you are eating, or in the bedroom.

Step 2: Commit to not being a zombie. This means no walking and using your phone.

Step 3: Remember, you are trying to improve your concentration the same way you are committed to being physically fit, so concentrate on doing one thing at a time. Start easy, with things like driving and/or listening to music or an interesting podcast and not using your phone for texting or email at the same time, there is nothing that urgent.

3. Like me, you probably have a number of browser tabs that represent various communication tools. Email, Messenger, Slack, Twitter.

Create one bookmark for all your communication tools and only use one window for these tabs. It’s much easier and safer for your mind to be able to open all these tabs at one time and easier for you to close them all at once. You simply don’t need your communication tools open all day. They work against your ability to concentrate. So, if you really want to get better at concentration, combine them into one window, open them only when you need them, then close them. Never add any other tabs to this window and close it frequently, especially during your long periods of flow time on a single project.

“At one time I thought the most important thing was talent. I think now that — the young man or the young woman must possess or teach himself, train himself, in infinite patience, which is to try and to try and to try until it comes right. He must train himself in ruthless intolerance. That is, to throw away anything that is false no matter how much he might love it. The most important thing is insight, that is … curiosity to wonder, to mull, and to muse why it is that man does what he does.” William Faulkner

Remember, the day before something is a breakthrough, it’s a crazy idea, so be gentle with yourself as you work on this.

The Single Most Important Attribute You Need In Order To Build Trust

Earlier this month I initiated the first steps in creating a new brand. My plan is to launch in the spring. In order to make this happen I need to engage a number of freelancers and industry experts. It’s not hard to separate who I will be working with by April and who I will not.

There’s one attribute that is apparent within days.

One attribute that people demonstrate that builds trust within days, sometimes even hours of first engaging.

It’s something so simple that it seems almost comical when people don’t do it.

It’s something that when omitted isn’t just a minor flaw in the overall value, it actually puts a crack in the base of the value. When it’s not there, everything falls apart.

Do what you say you are going to do. That’s it.

Every time you do what you say you are going to do you create a layer of trust. The more you do it, the thicker the wall becomes until it’s a moat and it’s very hard for anyone else to get in.

Do what you say you are going to do. How can it be that simple? It just is.

My 2018 Non-Negotiable List

I had hit rock bottom. I was mentally exhausted. I felt like crap even though I led a healthy lifestyle. What was wrong?

I wasn’t focused.

I was distracted.

I lacked purpose and discipline of where my attention should go.

I first wrote about non-negotiables in 2015. That year I even posted my non-negotiable list on the glass door of my shower. I saw it every day. I found the responses to the post to be quite polarizing. Some readers loved the idea of structure and rigid constraints. While others, reacted quite the opposite. For them, the idea of tight rules, without flexibility, hit a deep wound.

Then this year, in 2017 I wrote about creating filters in order to work less and have more free time. I’ve made it an annual process to set non-negotiables.

I personally don’t do well with rules put on me by others, however, when I put the constraints on myself and make them public, it works out well. I’m happier and more productive. I’m left only to battle my own ego.

2018’s Non-Negotiables

• My phone is no longer my alarm clock and thus is not welcome in my bedroom. I’ve purchased a small traditional bedside alarm clock that does two things. It tells the time and it wakes me up when I tell it to. Removing my phone from my bedroom removes the distraction of, well, everything.

• Up at 6am for one hour of “me time”, non-neogotiable. Going forward I’m very focused on never being rushed again, it’s a feeling I want to eliminate from my psyche. Once everyone else is up in my house I’m suddenly on call. Therefore, I wake up at 6 a.m. and go through my morning routine in peace, with no rush.

• No weekday drinking. I’m up at 6am on weekdays and I know I don’t sleep as well if I have even one drink since I’m not 25 anymore. I need to be operating at 100% everyday so I’m simply removing alcohol from my weekdays.

• My six, three hour, flow time, single project time slots are firm. I have scheduled three hour blocks for all of 2017 that are intended to be used for working on a single project. Work on one thing, undistracted for three hours. If someone asks me for an appointment during one of these times, the answer is no, there are many others time slots in the week and I use Calendly to make it easy for them to find an alternative. Lots has been written on the incredible power of flow, taking one subject or one project and working on it for a prolonged period of time without any interruption. I’m going to harness that in 2018. Want to know more about the theory of flow, listen to this Ted Talk.

• Thinking day once a month, scheduled throughout the the year. Like other items on this list, it’s scheduled in ink, it’s not moving for anything except a family emergency. This is one of the harder things on my list because there’s nothing really to do. It’s not easy to just spend a day doing nothing but thinking. I may make notes, but in a book, not my computer. I’ll walk a lot on these days, possibly go to an art gallery and find a comfortable seat and just observe. We minimize the value of time spent thinking because we worry we aren’t accomplishing anything. But just because everyone else is running around overstimulated and tied to their inbox doesn’t mean you and I need to be. If you want to read more on this topic, my friend Brian Scudamore wrote an article for Inc. on the topic.

Monthly Board Meeting with Winslowe. Jim Sheils developed the family board meeting and now that Winslowe is turning seven it’s time to implement the board meeting consistently and  in it’s entirety. The basic idea of Jim’s family board meeting is spending three hours with your kid, 1:1 (no grouping kids together), doing an activity of their choice, technology free (leave the phone at home), and then discussing the result of the activity. The fact is, very few of us spend quality time with our kids. Yes, we spend time with them, but uninterrupted and technology free? Rarely.

• Identify and schedule next week’s six projects every Friday. I will assign what projects I’m going to work on to each of the six three hour time slots allotted to flow time.

In their book, A Beautiful Constraint, Mark Barden and Adam Morgan do a fantastic job of laying out how having tight constraints don’t limit you, but in fact create an environment for creativity to flourish. Everyday we are hit with constraints and we have the choice of responding to them as a victim, a neutralizer, or a proactive transformer. By making a constraint beautiful we see it as an opportunity, not a restriction. The constraint becomes a stimulus to see a better way of achieving something or solving a big problem. So why not deliberately put a few in place? That’s what I’m doing with my non-negotiables.

My non-negotiable list isn’t about making my life so rigid I can’t be flexible. On the contrary, it’s about giving my brain less to think about. Having these non-negotiables allows me to be more focused, resulting in an incredible amount of flexibility and creativity.


Difficult Conversations vs Difficult Decisions

I was 29, engaged to be married, and operating a successful eight figure company I founded just five years before. At the time, I was avoiding a difficult decision and instead kept trying to leapfrog into difficult conversations surrounding the decision. This didn’t work.

The problem is, a difficult conversation shouldn’t come before a difficult decision. If we can successfully come to a decisive decision first, then the conversation becomes much easier. The challenge is that we tend to play out imaginary conversations in our heads and the emotions that surround it. This causes the decisions that need to be made to get blurry, mostly because there wasn’t a firm decision to start with.

At 29 I had little idea of how to be a good boyfriend let alone a husband. I had somehow taught myself to be a successful entrepreneur and a half decent leader but because I wasn’t prepared to make difficult decisions in my personal life, I was not having success with personal relationships. I just swept things under the rug and avoided decisions that needed to be made.

Difficult decisions take guts, often a willingness to suspend your own needs, and a realization that the pain is often far greater in the thought than the action.

I now look back on when I was younger and see that empathy and responsibility were these nebulous concepts. They didn’t fit with my world view, nor my need to feel secure. It’s very hard to make meaningful decisions when you are worried only about yourself.

Make decisions, be decisive, use data if you need to, but then stick with the decision. Then you are ready to have the difficult conversations.

What Are You Doing This Weekend?

A young man asked his father, “What are you doing this weekend?”

His father responded, “I’m going to exist.”

“Yeah, I know, I get it, but what do you have planned?”

“Nothing,” he responded.

“So you’re going to do nothing?”

“Maybe, but I doubt it.”

“That doesn’t sound fun,” the young man replied.

“Oh, it’s gonna be more than fun,” answered his father. “It’s going to be fantastic! I’m just going to be. There’s nothing more fun than that, you really should try it.”

We live in a world that is continually trying to discover more and more pleasure. We are training ourselves that sensory gratification injected into every sense organ will lead to happiness. But just existing, if you let it, can be incredibly fulfilling and pleasurable.

Instead of just existing, we end up as consumers caught in a shopping mall of instant gratification. The effect psychologically and physically is not only restlessness but also mind and sense organs that are clogged up with sensory overload and the inability to take in anything with clarity. But if we choose to just exist, breathe, eat, move, we can return to a less chaotic pace so our perceptual faculties are less polluted.

Try it, try just existing this weekend.

The Hard Part About Accepting Sunken Costs

Your fear of loss leads to a fallacy that in the business world is referred to as the sunk cost fallacy.

In Daniel Kahneman’s book, Thinking Fast and Slow, he writes in detail about how he uncovered an imbalance between losses and gains we hold in our mind. Kahneman writes that since all decisions involve uncertainty about the future the brain we use to make decisions has evolved an unconscious system for judging how to proceed when a potential for loss arises. This is where sunken costs come into play.

Sunk costs are time or money we’ve invested and we can’t get back. They are gone. But, we forget they are gone and we hold on tight to the fact we invested, either time or money. That’s the fallacy.

Seth Godin has a great example of this. He saw a sign on his neighbour’s front lawn promoting the company that was doing some masonry work on her house. The sign said: Quality Masenry. The most important word was spelled incorrectly! 

Seth inquired with the contractor, “What’s up with your misspelled sign?”

“I spent $1000 on the signs and I still have a few hundred of them left,” the contractor replied. 

Just because the guy spent a lot of money on the signs and still has a lot of them left over doesn’t mean he shouldn’t spend some extra money to get signs with his profession spelled correctly. The $1000 is a sunk cost. The amount he already sent is irrelevant. What actually matters, is the benefit of spelling ‘masonry’ correctly.

It doesn’t matter that you spent 11 hours researching a family vacation to Puerto Rico and now, because of the hurricane you shouldn’t go. Those 11 hours are gone. Your fear of loss leads you to worry about it, when you just need to move on to planning a trip to Cabo.
There’s an imbalance between losses and gains in your mind. So over time, the prospect of losses has become a more powerful motivator on your behaviour than the promise of gains. Whenever possible, you try to avoid losses of any kind and when comparing losses to gains you don’t treat them equally.

So, when it comes to having to make a choice between two options, say printing new signs or researching a new vacation destination, only consider what’s going to happen in the future, not the investments you’ve made in the past. The past investments are over, lost, gone forever. They are irrelevant to the future. They are sunk costs.