5 Reasons “Why” is such a Powerful Question


Toddlers often have more clarity and curiosity in life than most adults. Categorically, they aren’t afraid of asking “why?” to seemingly every question that has an obvious answer.

It’s no wonder that asking higher quality questions leads to better outcomes in your personal and professional life. So the real question is why do we not ask “why” more? Why do we assume we already know the answer, and become more preoccupied with asking what, how, when, and who?

If I had an hour to solve a problem and my life depended on the solution, I would spend the first 55 minutes determining the proper question to ask, for once I know the proper question, I could solve the problem in less than five minutes.” —Albert Einstein

So why is it important to stop asking the wrong questions? Why should you start with why? Here are 5 reasons to Start with Why:

1. What and How are Functional, Why is Inspirational

People, organizations, and teams who start with what they need to do, how they need to do it, and who needs to do it are short-sighted. They focus on plans, strategies, and tactics, missing the goal. Asking “why” is inspirational, it creates tightly aligned but loosely coupled teams, because while everyone on the team may be unique in their approach towards a solution, they are all on the same page regarding why they are seeking a solution in the first place.

2. Asking Why Eliminates Confusion

The best way to get context in any situation is to ask “why” a lot. Asking why eliminates confusion caused by pre-conceived assumptions, which are fueled by lack of knowledge, or more dangerously, partial knowledge. To err is human after all, so asking “why” defines a clear path and brings everyone on the same page. This doesn’t just extend to teams though, introspectively you can ask yourself “why” you are following your own life’s path in your day to day life, work, and relationships.

3. Asking Why Gives Your Endeavours Purpose

Do you ever feel like you’re working “hard” but not getting where you want to be life? Asking why is a great way to remind yourself of the size of the prize you are pursuing.

4. Asking Why Separates Achievement and Success

Have you ever felt luke-warm about an achievement? Perhaps you got a raise, scored that difficult deal, or just joined a new role, but you didn’t feel happy or successful? Achievement is defined by the “what” you need to do, and that’s not always aligned with the “why” you need to do it. This is precisely the saying “you gotta do, what you gotta do” is counter-intuitive. Instead, focus on “why” you must do anything at all, and you’ll realize that maybe you need to change direction to feel truly successful.

5. Asking Why Positions You to WIN

In business, good consultants and salespeople ask the customer what their needs are, when they want to generate results, and who’s involved in making it happen. Great consultants and salespeople start with “why” instead. They provoke their customers and clients to think differently, constructively challenging them to questioning them to question their assumptions, and ask “why” themselves. This is the difference between professionals who position themselves as an Authority vs. those who just offer a Commodity.


Inspired by Simon Sinek’s wonderful book: Start with Why

Persistence vs Perseverence


What 5 years of looking in the rear-view mirror of a rapidly growing digital marketing agency taught me.

It is in times of security that the spirit should be preparing itself for difficult times; while fortune is bestowing favors on it is then is the time for it to be strengthened against her rebuffs.”— Seneca.

I dreaded going into work. The environment was so toxic that you could feel the tension in the air. Business was great but the powers that be decided to turn the tables on me by re-writing my role. Work just wasn’t fun anymore. The last straw came when my boss told me to “never start a business” because I’d be a “terrible manager” and because “fax machines were expensive”.

“You’ve got to be shitting me”, I thought. So I quit. The decision wasn’t hard.

I felt relieved. Then I felt sick. What should I do next? Was I going to fall on my face and become a victim of my own self-fulfilling prophecy?

Screw that.

I decided to give it a go. What’s the worst thing that could happen? I’d work on building a business for 6 months and if I failed, I could have easily gone back to getting a job.

Fast-forward 5 years into my journey, I’m proud to be at the helm of one of Canada’s fastest growing digital marketing agencies. There’s a lot of learning left to acquire and many more mountains to climb, but I’m at peace knowing that my journey is going along the right path.

PS: Happy 5th Birthday Powered by Search!

I’ve never been the type to give up at anything, perhaps to a fault. The last 5 years have taught me that no matter how good or bad things are, having perspective, patience, and viewing the world on an even-keel are virtues that lead to positive outcomes.

There’s a thin line separating those who persist versus those who persevere.

Persistence is a skill whereas perseverance is a virtue. Sticking to your guns and doing the same thing over and over again without learning from your mistakes is a recipe of disaster, nay, insanity.

We learn by making mistakes. I’ve made more than my fair share. Hitting road block after roadblock, pummelling into the proverbial brick walls that hinder progress, the difference between persistence versus perseverance started becoming clearer.

If I had to have a conversation with myself 5 years ago on October 5th, 2009, here’s what I would have said to myself:

1. Strive to be amongst the top 5% in the world at one thing. Find your niche and own it.

I’ve been a digital marketer since early 2006. In a sea of opinions within the #SEO industry, I picked a niche no one was talking about — Enterprise Local Search. While all the other Local SEO’s were talking about optimizing single-location businesses, I chose to focus on strategies to rank 10, 100, or 1000+ locations.

Do you work in an industry that isn’t nascent or growing? Saturation is a blessing. The obstacle is the way. Find a way to be at the top of your industry by identifying pain-points and figuring out creative ways to solve them. How do you do that? Ask your boss, your co-workers, and your clients how you could make their work and life easier, better, and more meaningful.

2. You can Out-compete your Competition by Out-Caring Them.

We still regularly compete with corporate giants in the digital marketing industry who have more resources, budget, and sales-people than I do. 2 out of 3 times when it comes down to it, we win. Not because we’re cheaper or have more brand klout, but because we out-care the competition.

3. Punch Above Your Weight Class.

3 days after I incorporated my company, I was asked to speak to an audience of 1000 people on how to generate leads using social media.

I was worried. I didn’t have a deck, and the biggest audience I’d addressed at the time may have been about 100 people. This was 10x the size. Visualizing that many people in their underwear would have been a visceral overload (and not in a good way).

In hindsight I’m glad I was up to the challenge. That speaking gig lead to our first enterprise client (still working with us 5 years later). Someone at the event who represented a professional speaker’s agency approached me after and booked me for another speaking opportunity. Two weeks later, their competition booked me into other speaking opportunities as well.

Sometimes you just have to bite off more than you can chew to know how much you can really achieve.

4. It will be Hard. Startup Life Can Suck.

Stress and depression are real facts about building a company one brick at a time. I’ve struggled with bouts of depression and weeks where stress is through the roof. It’s not pretty, but it is worth it.

On a layover at Atlanta airport after a client pitch. That day was 18 hours long. The deal took 5 months to close after, but it was well worth it!

There are days where it is Entrepreneurshit. Suck it up and continue shipping. It will get better but if it doesn’t get help.

So how do you deal? Take your pick: Surround yourself with common-minded peers, meditate, and maintain a journal to count your successes to balance your failures.

5. You Can’t Scale Giving a Shit.

Like most first time CEO’s, I’ve been challenged to grow from a Maker to a Manager. We’ve scaled quite a bit and then some, starting as an army of one and now pushing 50+ bright, passionate, and curious marketers.

Training our team of 6–7 back in 2012.

Revenues grew from a few hundred thousand dollars to mid-single digit millions in the same time period.

Initially, I wanted a company of no more than 10 people. Then it was 15, then 22. Our merger changed that and before I knew it we had over 50 amazing team members and over 200 clients.

There was only one-reason we grew the way we did…without a sales team, without recruiters, and without funding — We all gave a shit about our team, our clients, and our community.

6. Money isn’t Everything. Be a Good Steward of your Industry.

There are hundreds of different ways to get bigger, faster, with less work, and by cutting corners. But what is your legacy? Do your peers respect you or loathe you? Or worse…they don’t even know who you are, or what you stand for.

You can have everything in life you want, if you will just help enough other people get what they want. — Zig Ziglar

We spoke at local accelerators, started our own meet-up, organized our own conference, planned agency foosball tournaments, and I even taught SEO at a college.

Inboundcon 2013. Our 1st ever annual conference.

We spoke for free, arranged meet-ups for free, and broke even on our annual conference.

Why? Because it was the right thing to do. And because it was a lot of fun doing it.

Perseverance is persistence applied towards positive outcomes. The last 5 years have been fun, not so fun, and everything in-between. But without a doubt, it was worth it and as long as it continues being that way, I’m in this for the long-haul.

The next 5 years will bring different learnings, new challenges, and I will be a different version of “me” by then. No matter what’s around the pike, I’m looking forward to living in the present, and giving those who played a pivotal role in the journey thus far my very best.

26 Things I Learned at Age 26


“Love yourself like your life depends on it, because your life does depend on it.”

At age 26 I want to share a few things I’ve learned over the years about living a prosperous and purposeful life.

1. Never Accept Anyone Else Telling you What You Can or Cannot Do.

No one can decide what you’re capable of except you. Don’t let anyone choose which lines you want to colour in.

2. If You Don’t Go After What You Want, You’ll Never Have It.

The biggest enemy of progress is using the phrase “someday”. Successful people don’t wait for opportunities — they create them.

3. Focus on Possibilities instead of Problems.

Problems are often opportunities in disguise.

4. Create More than You Consume.

We spend our lives in front of screens of various shapes and sizes, scanning, reading, and consuming. In a garbage-in garbage-out world, share your wisdom by creating a wealth of knowledge rather than only consuming it.

5. The World Doesn’t Owe You Anything.

There will be times where the world will seem unfair to you. Your work will go unappreciated. Your partner will take you for granted. Your boss will take credit for your work. Let’s hope none of this ever happens to you (I have been fortunate in this regard) but if it does, remember that the world owes you nothing and that your future is in your own hands.

“We cannot change the cards we are dealt, just how we play them”.

6. Good Actions Count More than Good Intentions.

What you do matters more than what you intended. No one can read your mind and no one owes it to you to really try.

7. Be Kind to your Body and Your Soul.

I think it’s safe to say that every 10 years, one can look back a decade and feel markedly different about their physical fitness, levels of energy, and drive. As we age it is important to take care of your mind and body.

Get out more. Go take a walk. Get off the computer. Take a 30 Day Health Challenge.

8. Expect Nothing in Return for The Things You Do for Others.

You don’t need to believe in Karma to do good things for others. Be selfless in helping others and do not do it for any other reason but brighten someone else’s day.

9. Strive for Happiness and Nothing but Happiness.

Strive to be happy and content no matter what you spend your time and efforts on. Focus on maximizing your happiness over everything else: status, money, power, ego, etc.

1o. Failure is a reflection of an Event, not a Person.

When you fail learn from the experience. Life is full of chances (whether you create opportunities or chance upon them) and learning from your failures will help you shape into a better person.

11. Don’t Think Twice about Saying “I Love You” and “Thank You”.

These words are free and should be shared regularly. It is not enough to expect your partner, family, or friends to ‘understand’ that you appreciate them. Verbalize it.

12. You aren’t Truly Wealthy until You Have Something Money Can’t Buy.

Money is a great enabler and can open many doors but having money is not the same as being wealthy. True wealth comes from the sense of freedom and contentment that is not easily displaced or replicated.

13.Regret will Cause You More Pain than Heartbreak or Broken Bones.

Speak your mind, do the things you want to do, and take full responsibility for the consequences (good or bad) but don’t look back and say “I wish…”.

14. Spend a Few Moments with Yourself Alone, Every day.

Take a couple of minutes every day to be at peace with yourself. If you’re into meditation then take 10 minutes to do that. If you aren’t, spend the time grounding yourself by appreciating what you have today and preparing for the dreams you want to pursue tomorrow.

15. Choose Your Partner Carefully. They Can Make Your Life 100X Better or Worse.

I lucked out with my wife Amy. I couldn’t imagine life without her. She is a constant source of joy, happiness, inspiration, and the best friend I could ever ask for. All relationships take time, effort, and understanding but having the right partner can make life 100X better.

16. Maintain Great Relationships with your Aging Parents.

As I get older I appreciate the things my parents have done for me more and more every day. I can imagine that when I become a father myself this appreciation will only grow. Life’s best moments are fleeting and in a fast paced world it’s important to continue the relationships we’ve had with our parents as kids.

17. There’s a Song that Makes Everything Alright for 5 Minutes.

For me that’d be U2’s Electrical Storm. Songs have powerful effects on your cerebral cortex, bringing back vivid memories of sights, sounds, and smells from important times in one’s life.

18. Live a Humble Life.

No matter what you’ve accomplished you’ll find more serenity in life and attract the right people into it when you’re humble.

19. Learn when to Disconnect.

Your body wasn’t built as a productivity machine. When you are feeling burnt out it might be time to disconnect and go on that vacation you’ve been planning for a while.

Better yet, turn off your notifications, stop checking your email, and turn off your phone.

20. Look for Work-Life Fit, not Work-Life Balance.

Your boss and colleagues count on you to pull long-hours and you may be dissatisfied with your job. Most people aren’t actually motivated by money to switch jobs but instead look for w0rk-life balance.

At least in Tech and Marketing, it doesn’t really exist. Instead, look for work-life fit. Work-life fit focuses on allowing employees flexibility in their working hours, allowing them to balance work along side personal goals or duties.

Many startups and companies strive for work-life fit including my own agency at Powered by Search.

21. Learn Something New Every Day.

Some call these “life-hacks”. No matter what you call them, spend your downtime learning new things that can enrich your life. I learned how to pitch better on my daily drive into work by listening to Zig Ziglar audio books back when I was around 19-21.

22. Learn to Listen Twice as Much as You Talk.

Everyone wants to be heard. It pays to listen to anyone you speak to and really understand what they are saying instead of thinking of your next response while they’re talking. This way we speak with each other instead of at each other.

23. Break Big Projects into Tiny Blocks.

When I was starting my undergraduate studies and working a full time job I remember it being fairly difficult to complete intermediate finance exercises and create scope of work proposals at the same time.

I eventually learned to “chunk” projects and problems into much tinier bits. In it’s most rudimentary form I’d chart out any given project into an outline first and then work out individual sections one-by-one.

24. Pick the Something you Love and Be amongst the Best in the World at It.

When thinking about your life’s work you don’t have to settle for what’s proven. What’s important is to pick a passion that you’ll likely never get bored of and then be the best at it. Success and money will come in spades as long as you choose something that others also care about.

25. Always be Hungry and Fight Complacency.

Never get too comfortable in life. Seek new challenges regularly. At work as your boss to help set goals for you that you can work towards if you aren’t allowed to set them yourself.

26. Let Go of Your Anger and Jealousy.

Seriously. It isn’t worth it and the only person you’re holding back is yourself.

A good life is when you assume nothing, do more, need less, smile often, dream big, laugh a lot, love with complete abandon, and count your blessings every single day.