What’s Your “Why”?


As the inaugural post to kick things off with my little digital soapbox, I wanted to put forward an initial challenge, of sorts.

But first – 20 seconds of house-cleaning…

As some of you may know – I’ve “retired” my brand, and presence in general, in the affiliate marketing space. I’ll soon be closing the doors over at TheLazyMarketer.com (though I might leave the blog archived somewhere), and pulling down all the (remaining) legacy products.

For the record – there’s no bad blood or anything. And affiliate marketing hasn’t “died”. (Lots of people are still doing very well with it).

The bottom line is that I’ve simply lost interest. Both in terms of running campaigns myself – and in terms of talking about it as a business model. I’ve lost interest for a variety of reasons… some of which I’ll touch on this post. But that’s the gist of it. It’s just time to switch gears.

So what’s this site all about, then?

This site has been a long time coming. Where “The Lazy Marketer” was a site about a given business model – this site goes deeper. I’m not just going to focus on the usual schtick (marketing tactics, insights, etc.). I’m going to get a bit more cerebral, and talk more about the “internal game”, as an entrepreneur… and also just in general.

So much of what determines your experiences, your results, and what you “get” in virtually every area of your life – really comes down to how you think.

And while I don’t have all the answers (by any stretch) – the one thing I am sure about, is that half the battle (or more) of my own journey so far, has been waged between my ears.

So – while that’s admittedly vague – in a nutshell, this is where I’ll talk about the experience of being an entrepreneur. And not just the mechanicals. And often, these brain-dumps will have nothing to do with business.

Anyway. Speaking of brain-dumps – let’s get back on point…

Why do you actually want to be ______________?

Mentally insert whatever your predominant objective is at the moment – whether it’s biz-related or not – into the blank space above. (Maybe the word is “successful”, or “more organized”, or “my own boss”… etc. Whatever’s currently applicable.) Got it?


Now, let’s explore that by asking “why”… and taking a trip down the rabbit hole, in the process.

The best way I can do that, is to take you on a journey into my own experience – focusing on pivotal moments over the past decade. Because not only has my “objective” changed over time… but so have my reasons.

These are the standout benchmarks of my own motivational evolution, thus far…

Initially, my journey into entrepreneurship started with the choice between either “doing something with my life”… or trying something that seemed a lot more interesting.

I was 19. I had just completed a 9-month “college course” at a place called Capernwray Harbour Bible College.

[alert style=”grey”]

Quick contextual background: My parents had insisted that I enroll in some form of post-secondary education after I’d graduated high-school. And since I was nearly as fervent about my faith (at the time), as I was passionate about avoiding anything remotely academic… I found the shortest possible “post-secondary college” that I possibly could. 

It only took 9 months to “graduate” from Capernwray, there were no tests, papers, or homework involved… and it was out on Vancouver Island. A fairly exotic location for a kid that had spent his life to-date living in Northern Alberta. It was a great experience, I made a lot of good friends, and the staff at Capernwray are wonderful people with the best of intentions.


Anyway, with my post-secondary obligation out of the way, and with zero interest in further education – or embarking on a “career path” – I moved to a town called Kelowna, in BC’s beautiful interior region. The weather was drastically better than where I’d grown up.

I don’t remember being particularly bothered with the prospect of just “coasting” for a while. Maybe working a few filler-jobs for awhile, and taking the odd surf trip when I could. However, this wasn’t due to a lack of ambition. It’s just that – at the time – my ambitions were more image-related. I idolized the notion of becoming something “exotic”, in contrast to my current state of self-perceived mediocrity.

The prospect of becoming a legitimate “West-Coast Surfer” was very appealing. Even if I wouldn’t have admitted it as being a tangible pursuit at the time. And so, that’s what I set out to do.

Now – for the sake of keeping this breakdown somewhat organized, let’s summarize each “benchmark” – starting with my first notable “why”…

[blockquote style=”blue”]

Benchmark #1: Moving out West

What I Wanted: To embrace the “surfer” lifestyle – and break far away from the typical direction most of my peers had taken (getting a degree, working in the oilfield, etc.).

Why?: So I could feel as though I was interesting & exotic.


As a quick aside – see what happens when we honestly evaluate the underlying “why” behind our aspirations? So much of what drives us has to do with our own self-perception… far and above any associated, tangible benefits.

Anyway – moving on…

I’d say that this goal – becoming a “surfer”, both in practice and in essence – lasted about 2 years. During this time, I did indeed do my fair share of surfing – both in Canada and abroad. Overall, it was a great experience. Mostly because I could discover first-hand that, beyond the actual sport itself (which is equal parts zen, skill, and adrenaline), there is nothing special or exotic about people who surf. Even if the sport itself is indeed special & exotic.

Doing something interesting isn’t enough to make you interesting. (But more on that, some other time).

So, in time, I came to realize that I actually didn’t want to be a “surfer”. There was nothing inherently compelling about the surfers I’d met thus far. The vast majority I’d met were either in the “aimless burnout” category… or the “water-jock” category. Not exactly my scene.

I began to find greater appeal in becoming someone who could actually influence a culture… rather than just associate with it. It wasn’t enough to just experience surfing, or to embrace the associated lifestyle. Participation wasn’t enough. I wanted to trail-blaze… to leave an impact.

I would say it was this initial realization that served as the “spark” for my entrepreneurial journey. And in the beginning, the aspiration of becoming noteworthy far outweighed the prospect of wealth (or trappings thereof).

Which brings me to the next benchmark…

[blockquote style=”blue”]

Benchmark #2: Starting “CR Longboards” – a downhill skateboarding company

What I Wanted: To simultaneously become a “somebody” in the culture that I identified with, as well as do my own thing, full-time.

Why?: So I could feel as though I was more than just interesting – but also important.


At this point, I think I’d just turned 20. Long story short, with probably about $500 in the bank (and $200 left on the credit card), I decided to jump off the proverbial cliff… and see if I could hit the ground running.

In retrospect, this wasn’t so scary. It’s easy to “bet everything” when you don’t have much to lose. And all I was walking away from were a string of shitty jobs. Between moving furniture, cleaning carpets and working in a warehouse… it’s not like I was walking away from a career. (This is actually a huge advantage when you’re a fledgling startup. Moreso than most people realize.)

So I quit my current dead-end job at the time, I spent all my remaining cash on plywood and tools – and I managed to rent a “workshop”… which was essentially a glorified garden shed in some guy’s backyard. And I got to work, making longboards from dawn till dusk. When I’d get home at night, I’d spend whatever remaining energy I had on my shitty PC that barely worked, posting each board on eBay, one by one.

As well as self-teaching myself to build a website with Dreamweaver 4.0, which is basically a step up from using DOS. (I still keep it online, purely for sentimental reasons)

For the first few months, I literally had to choose between buying proper supplies (router blades, etc.) or proper food. If I bought quality supplies, I’d eat sausage & cheese packages from 7-11. If I skimped on supplies (shitty router blades, cheap masking tape, etc.), I could afford luxuries like non-processed groceries. It wasn’t exactly a “lifestyle business” back in those days…

But somehow, I made ends meet. And the business was actually supporting me.

After a few months, I could basically earn the equivalent of a shitty job… but on my own terms. And with my own ideas. It didn’t give me many options – but it was a really cool to experience what it’s like to actually turn an idea into a livelihood.

This is something I’ve since done many, many times. And it always feels the same. The process of finding the courage to just “jump”, and figure out how to land later – has probably been the most valuable asset in my “career” thus far. That is truly what separates dreamers from doers. Everyone has ideas, intentions and plans. Doers tend to dive in before their planning is “complete”, and just figure it out as they go.

Anyway – I quickly hit the ceiling with “CR Longboards”, in terms of what I could physically manufacture – without offshoring production to China (which didn’t interest me, and involved considerably higher stakes).

This, combined with the fact that I was still very much an amateur in terms of marketing processes, pricing & positioning, and biz-building in general… meant that the business had definitely reached its potential ceiling. At least in its current form, and with an inexperienced “me” at the helm.

And it wasn’t a particularly high ceiling.

It didn’t happen overnight, but at some point during this process, I began to notice a gradual internal transition towards more pragmatic aspirations. Namely – making more money, and thus having more options in life.

As the “fog” of my own idealism began fading against the backdrop of stark realities – always scrambling to make rent each month, having zero prospects of traveling, and not seeing a way to feasibly improve things without simply “working harder” – I began to see the simple merit of simply doing what worked as a business, and then pursuing my passions outside of that… rather than forcing a business to work inside of my “passion spectrum”.

And this newfound “appreciation”, if you will, is what sparked the next benchmark in my little story…

[blockquote style=”blue”]

Benchmark #3: Pursuing a lifestyle business model – rather than a “passion business”.

What I Wanted: To simply have more options in life. To travel if and when I wanted to. To be able to have nice things, if I wanted. It’s not that I wanted “stuff” per se. I just wanted to be in a position where I could do/buy something if I wanted. I was sick of scraping by… and I was willing to trade “passion” for a taste of the other side.

Why?: So I could feel competent and powerful. I felt very unsuccessful at the time – which I allowed to cut deep into my psyche.


I was still making longboards (just to get by), but by this point, my sole aspiration was to figure out a way to build a more scalable (and passive) revenue model, ideally over the internet.

I’d literally survived by selling my boards on Ebay (mostly), as well as a few each week directly from my website… so I’d had a taste of what was possible by using the internet as a marketing platform. For this reason, I wanted to discover a business model that could leverage the internet.

It took me a long time to figure out which way was “up” in the compelling & confusing world of internet marketing. And like most arenas of opportunity – most of what glitters is fool’s gold.

My first inclination was to pursue the “online magazine” model, and make money by selling ad-space. I did this in the boardsports industry, as well as in a few general interest markets (like “funny picture” sites, etc.) While the model was certainly viable – I was able to get the sites collectively earning about $1K/mo in a few months time – it also proved to be very difficult to maintain. Let alone scale to something beyond supplemental income.

The “content model” is no cakewalk. (Not even back in the days when it was far more viable).

Eventually, I stumbled into the direct marketing model – selling stuff online with long form salesletters, list-building & relationship marketing, product launches… etc. This was definitely a crucial training phase in many ways – but it’s also an arena that’s rife with exaggeration, misdirection, and in some cases, outright scams.

Like most who “make it”, I’d eventually realize that the real money is in the fundamentals. The math of marketing. Not the peripheral nuances, or “secret tactics”.

Anyway – I started to cut my chops in the world of direct marketing. I had a couple consulting gigs where I was able to put some of this theory into practice (salesletters, launches, email campaigns, etc.) – and though my first work was laughably bad… it still worked. And I was starting to figure shit out.

After about a year of getting progressively more polished with those clients – as well as launching a product of my own (a course on utilizing joint ventures to drive sales – an area where I was actually pretty talented), I’d managed to build up a somewhat-passive full-time income, and the model definitely showed promise. I certainly wasn’t a 6-figure baller by any stretch – but I was definitely on to something.

So, at least on paper, things were starting to look up. Looking back, though – this was definitely one of my weaker stages, as a person. On a subconscious level, I’d gradually begun to equate my own sense of worth with material success.

I was also obsessed with the idea of success in general. It saturated most of my thoughts. It invaded every conversation… which must’ve made me a total bore. I had fundamentally changed – and not for the better.

It would take a long time for this trend to subside. Even after I’d “succeeded”.

Speaking of which…

[blockquote style=”blue”]

Benchmark #4: The stars finally aligned, and one of my projects took off in a big way…

What I Wanted: Put simply, I just wanted to make it big. And after things “clicked” – I just wanted to push the envelope as far as possible.

Why?: So I could feel as though I had transcended “normal”… and attain some sort of legendary status from the perspective of my peers. I also wanted to feel vindicated by what this pursuit had cost so far (a few friendships, and a decline in health).


As I alluded to above – I finally had my “big break”. This happened just after Sarah and I had gotten married – and in fact, the big break happened while we were on our honeymoon.

Long story short, a small experiment in a consumer (B2C) software market proved to be very successful. It made over $9,000 on day one. Not a bad start 🙂

Among other things, this opened my eyes to the simple economics of simply matching existing demand… rather than always trying to develop some “breakthrough”, world-changing product. I could simply cast my line where there were obviously fish.

And it was also far easier to tap 1% of a massive, obvious market – than trying to “own” 90% of something speculative, obscure or emerging. (And generally, that “1%” equates to far more profit than the “90%”).

And so, during this phase, I largely utilized affiliate marketing to tap these “plain sight” markets, simply because I could be up and running in a market within 48 hours – instead of spending months developing my own product.

It didn’t take long to build up a substantial 6-figure income by doing this. Shortly thereafter, I also became well-known in the affiliate industry itself… building a sizeable audience and brand in that market simultaneously.

In short, I was killing it.

Sarah and I would spend months at a time traveling the world. We were buying up revenue properties, and I started collecting sports cars.

At this point, I also became feverishly obsessed with my work. I was glued to my laptop, almost 24/7. I viewed what I was doing as somewhat of a golden goose… and I wanted to collect as many “eggs” as possible, before the game was up.

I was certainly proud of my results… but the whole experience began to feel empty. For example – the first month that broke the $10,000 barrier was a huge milestone. I remember almost crying in excitement.

In contrast, the first month where I broke the $100,000 mark barely registered a second-glance. It quickly became apparent that the pursuit of money, in and of itself, was tiresome and pointless. It literally makes no difference emotionally, or in many cases even financially – once you surpass a certain (relative) level of comfort.

Especially when you’re not producing anything, or making a noticeable impact. (In other words – affiliate marketing).

During this time – I’d also really let my health slide. A lot. 

At the height of my “money phase”… I was edging on 250 pounds. And at 5 foot 11″… that’s about 70 lbs overweight. I was a walking paradox. Highly successful on paper, but physically – I looked, and felt, like total shit. (I’ll expand on that in a later post, sometime).

I found myself aimlessly pursuing “more”… for the sole purpose of milking the proverbial cow for all she was worth, in case I woke up one morning and found that the game was up.

And then, something opened my eyes to just how “small” I was thinking. And how my pursuit of “more” had, ironically, kept me (far) below my true potential…

In a nutshell, I sold off my most successful affiliate site at the time, for a 6-figure amount. This site had been instrumental in building the revenue line and market exposure for the vendor I was promoting. They bought my site as a way of consolidating their overall presence…

…and then, not long afterwards – they turned around and sold that brand (the one I was promoting) to a major competitor for $100 Million. A sobering reminder that I was definitely on the wrong side of the equation… and not just in terms of money. I’d “made money”. They now had enough capital to build a generational business and legacy.

I was sick of simply enriching myself. I wanted to build an enterprise. A culture.

Not just a “big income”.

This served as a catalyst for seriously re-evaluating what I was spending my time on. (And trading my health for).

[blockquote style=”blue”]

Benchmark #5: Poignantly realizing that I’d been selling myself short for the sake of aimlessly “milking it”.

What I Wanted: I wanted to do something important, and something that I could be proud of – even if it meant taking an income hit. I was sick of the affiliate model, and I was sick of the product launch treadmill. Most of all, I was sick of feeling like an empty lone-wolf that was doing nothing but “making money”.

Why?: I’d underestimated the importance of feeling important. I wanted to have a purpose, again. Empty success had taken its toll.


Almost immediately, I dove in with reckless abandon in my pursuit of building an actual brand. Something I could be proud of, and something I could parlay into an actual corporate culture.

The first attempt was with a link prospecting platform (in the SEO space) called “ActuallyRank”. It was successful out of the gate – but also short-lived. The business model relied on a transient process. I had to close the doors, as the process we facilitated began to lose effectiveness.

Lesson learned – don’t build a business on a fad.

The second attempt was a user-driven review platform with a twist (helping users monetize their content), called Ukritic. Initially, the project was a success. But it was also quite complicated, it had a huge dev cycle (1 year), and it required a lot of content priming – which meant bringing on a team of writers to pre-populate the site before we went live.

And ultimately… it depended on Google’s “good graces” to initially pick up steam. In the end, the site simply never gained Google’s favor. (And make no mistake – we were no amateurs in this respect. I’d rolled hundreds of organic affiliate sites prior to this.)

The bottom line was that Google didn’t like our business model, period. And therefore, they wouldn’t rank us.

Lesson learned – don’t build a business whose lifeline depends on the decision of some third-party, outside of your control.

Shortly thereafter, I decided to switch gears. An opportunity came up where I was able to essentially handle the entire marketing operations of a startup (PosiRank) from its inception. Since it wasn’t my company – it took awhile to get used to the advisor role (and not running the show), but regardless – what I’ve been able to learn from the process has been substantially more enlightening than simply running affiliate campaigns.

It took a while to get things rolling, and to figure out how to make our sales funnel/processes work… but as I write this (in December of 2014), PosiRank now trends at $3.6MM in annual sales. Which is pretty impressive, IMHO.

(Obviously, I can’t take all the credit. The founders – Dave Kelly & Alex Miller – are world-class entrepreneurs, and the rest of the team is unusually talented.)

Currently, PosiRank provides full-time employment to nearly 20 people, it has contracts with nearly as many vendors & suppliers (including myself), and it provides consistent work for a remote workforce of almost 600 people in the US (who write content), and a team of 50+ in India (who handle platform setup & content distribution).

And this is where things really hit home with me… Two years ago, this was all just some idea on a napkin. And now it’s a million-dollar startup that creates a livelihood for an entire culture of people, and directly impacts their lives.

There is no feeling that can compare with knowing that, and I’m honoured to be a part of it.

Years ago – my “work day” used to consist of neurotically checking my stats every 5 minutes, emailing a few freelancers who did various tasks for me, and planning the next “launch” or site rollout. Wash, rinse, repeat.

Profitable, empty and boring.

These days… it’s a totally different story. There’s a lot more on the line, and heaps more responsibility – but it’s awesome to work with people who I call friends, every day, and build out strategies that will directly impact everyone involved. I’m never going back.

And my role with PosiRank is just the beginning of my ex-affiliate life. With my own SaaS platform startup in the works as we speak, it’s time to see how I can grow the next company – this time, as a founder.

From time to time, I’ll update how that’s going on this blog.

Which brings me to the final “benchmark” in this series, which is where I’m at currently:

[blockquote style=”blue”]

Benchmark #6: Doing things for the sake of making an impact – both with our customers, and (almost moreso) with the team… where personal gains are secondary, and where the “big money” is deferred to the long-game – rather than asking “how much can I make this year?”

What I Want: I want to grow my company (BigPixure) and client projects (PosiRank) to a point where I can build a legacy – both in our industry, and in the lives of everyone we work with, and who works with us.

Why?: Because it makes me feel important. And because it has a tangible impact in the lives of others – which gives me a great sense of purpose.

I basically traded the youthful vigour of my 20’s for the pursuit of “success”. I think spending my 30’s on building a legacy that positively impacts other people (not just myself) will be far more fulfilling. So far – it seems like it will be.


Let’s wrap things up, folks…

Hopefully, this has been an insightful (or at least voyeuristic) journey down the rabbit-hole of my “internal game” as an entrepreneur – from the perspective of evaluating my “reasons why” at each pivotal benchmark.

In my case, it’s quite obvious that a sense of importance has been the recurring anchor-point for what seems to drive my “happiness meter”.

During the stages where my “why” was not centred around feeling important – I was generally unhappy, regardless of the tangible outcomes. And likewise, when my “why” was congruent with desiring a sense of importance, I was far happier. Again, regardless of the tangible outcomes.

Yes, it’s important to do things that are economically viable, and give you options – to be sure. But if I had to do it again, and start from scratch… I would definitely ensure that my baseline “why” was always congruent with importance. Regardless of what I needed to do economically, or what temporary measures needed to be taken. I would ensure that my end-game was centred on feeling important.

The same goes for altruistic objectives – philanthropy, helping others, etc. Even with these higher social aims – your “why” must be congruent with your actions, or else you’ll burn out.

[pullquote align=”left” background=”on”]He who has a “why” to live can bear almost any “how”.  Friedrich Nietzsche[/pullquote]

I can only speak for myself, but having tasted “the other side”, and in general having done enough stuff in my life to realize that accomplishing “goals”, in and of itself, isn’t enough to make you happy – I believe that closely evaluating your own aspirations, and motivations, throughout your own series of benchmarks – is a very invaluable exercise.

Because once you come to understand what triggers your own sense of fulfillment – all it takes, at that point, is to simply change course (if necessary), and visualize a new objective. One that’s congruent with your ultimate “why”.

This is bigger than a given business model, or economic situation. It is understanding that the underlying motivations for whatever your current aspirations are, must align with your highest ideal.

Trust me – this will make you far happier than “success”.

So, I’ve laid out my cards. My “why” is a sense of importance.

What’s yours?

(Think carefully – this is one of the most important questions you’ll ever answer).


~ Chris Rempel

Facebook Comments

About the author

Chris Rempel

Founder, marketer, writer, futurist.


  • Hi Chris,
    I think that every businessperson, including myself, need to pass his hero’s journey.

    It needs to start somewhere. I found that my first “why’s” were very similar to yours – to be independent, feel competent, have more time, have freedom to be able to do what you want, to get more from your life, etc.

    After this stage, however, most successful people need to feel the meaning. And this meaning is generally related to being important influencer of other peoples lives. This is IMO the end journey of the entrepreneur.

    You probably underestimate your role as motivational person for new business people – including myself (TLM era). However, now you have direct impact on other peoples lives (your workers, collaborators) and it’s equally – or even more important. Congratulations and keep up the good work 🙂

  • Hey Chris, Great realizations and an even greater life story, as recounted above…SO FAR anyway! 🙂
    VERY well done on growing as a person and realizing WHY we are ALL really on this planet together!
    I wish you ALL the success your dreams may bring. You are truly an inspiration!

  • Hey Chris, great post, with some reality checks and “THINK” moments
    …like this bit “…the first month that broke the $10,000 barrier was a huge milestone. I remember almost crying in excitement.
    In contrast, the first month where I broke the $100,000 mark barely registered a second-glance. It quickly became apparent that the pursuit of money, in and of itself, was tiresome and pointless. It literally makes no difference emotionally, or in many cases even financially – once you surpass a certain (relative) level of comfort.
    Especially when you’re not producing anything, or making a noticeable impact. (In other words – affiliate marketing).”

    …seen some other peeps who made it saying the same thing, but it causes a little internal fight – I’m not there yet and though I know what you said is true, part of me kind of goes “NO Way, bullshit, you spoiled mofo…” 😉

    Anyway, are you planning to share your story and lessons and where could I subscribe for the updates
    …Where’s the optin man?! 🙂

  • I second what Krystian said… you helped so many people, myself included. I may have never had the success I did if I had not gotten The Lazy Marketer Guide

    I hear what you’re saying though about the “golden goose.” I was the same way, and then that golden goose died. Actually, it was dying a slow death, and I realized this, and so I tried to start my own product in that same B2C space where you had your $9k day. That project has failed miserably and I have lost virtually all of the $100k plus I had saved up as a result of my success

    So my “why” is basically back to Benchmark #3. Getting back my old life. But I did feel a bit of meaninglessness as well, although when that happened, I reminded myself of all the amazing experiences I was able to live out, and how I was able to live life on my terms a lot more than most. I think the biggest toll it took on me was attaching my self-worth to my success. Now that I’ve lost almost everything, I find myself in a self-loathing, anxiety/depression ridden state just about all the time

    I think it’s OK for your “why” to be money-driven, so long as you don’t let it define you, and you work to build assets that can’t be taken away at the drop of an algorithm change/offer going down, etc. Especially when you know your own weaknesses. I know I don’t have the intellect you possess Chris, so I really don’t see myself coming up with an original service like the one you are launching

By Chris Rempel