How To Know When To Quit

How To Know When To Quit

When we returned home from filming the Raising Global Citizens documentary, a question began to form around the edges of my weary mind: “How do I know when to quit?”

This blog answers that question…


We’d just returned from Beirut, Lebanon, a place that is, in many ways, the quintessence of the vital and indomitable human spirit. So inspiring did we find this sacred and storied place that we couldn’t help but allow it to seep into our veins — which would prove requisite for what was to follow.

Jet-lagged, I’d made an impromptu sleep cocktail of Gabba, whisky, with a splash of melatonin, and a garnish of 5-HTP. It wasn’t working yet; I was lying wide-eyed and awake. At that point, the Raising Global Citizens film project had already been 11 years in the making (admittedly, with a 4-year break following the first attempt in 2008 and 2009). It had cost all our savings twice, which was enough to stave off sleep on any good night, and I had a sinking suspicion that the hardest part was still in front of us — turning hundreds of hours of footage from 15 countries into a 90-minute documentary.

How much would it cost? Could I find the right people to edit it? How long would it take? Would anyone even watch the damn thing?

I’ve always believed that solutions and answers to all those questions exist in the vapours of possibility just waiting to crystallize through the advent of time. But again, how much time and what would become of me in the process?

You see, a popular question I was often asked after I’d sold Naked Underwear was, “Would you do it again if you knew it would be this hard when you started?” In that case, the answer was still yes, but the rub with these creative and entrepreneurial projects I knew all too well.

Yet, my blessing and curse in life is not giving up. The writing was never, as they say, on the wall for me, and I’d cling to creative and entrepreneurial projects and pursuits until my fingernails fell off.

Persistence is a cultural virtue (of which I agree), and of the many great persistence stories, I was always partial to that of J.K. Rowling — living on welfare while writing Harry Potter.

I’ve always believed that solutions and answers to all those questions exist in the vapours of possibility just waiting to crystallize through the advent of time. But again, how much time and what would become of me in the process?

Persistence, as a method and strategy, worked for me — as I share in my book Getting Naked— until it didn’t. Here I was again, already existing precariously close to the “b” word … that being “burnout” not “billionaire.” Which led to a question I was lying awake thinking about… “Was there also moral virtue and heroism in knowing when to say enough is enough?”

There’s a catch though. As blogger extraordinaire Scott Young points it out: “The easy spaces in life, with guaranteed wins for little effort, are crowded. It’s only once you venture past this, where you need persistence, vision and drive, do you start seeing rewards.”

Yet, Young continues, the reality is,

 “The easy spaces in life, with guaranteed wins for little effort, are crowded. It’s only once you venture past this, where you need persistence, vision and drive, do you start seeing rewards.”

“Sometimes your ideas and vision don’t match reality. What you’re trying to do isn’t going to work, staying stubbornly in the same direction can cost you much more than just pride. Every decision you make to keep going faces a trade-off. On the one hand, by quitting too early and too often, you never get past the hard parts and into the areas where your effort may pay off.”

In that way, this question, “how to know when to quit,” led me to the creation of an internal and actionable process I’d follow when deciding to, or not to, keep on keeping on, hold fast, go for broke… You get the point! 

Never had any quit as a young runner



  • To Quit or To Break?

My entrepreneurial kryptonite has been taking the three-week holiday. I muse over this in blogs, drinks with friends and at least once in a while after a solid work bender. All signs that fatigue has led to an anxious frustration where the emotional stakes are artificially inflated and make it hard to keep going. Sometimes all that’s needed to refresh is a proper, and I mean proper, mostly unplugged, not answering calls or emails, break of up to one month. Because, let’s be honest with ourselves, that first week off for vacation, we’re still unwinding our central nervous system and to-do list, and the last week, before heading back, we’re winding it back up. So the proper rest and recuperation only happens in the middle part of the vacation...and few days just isn't enough.

  • Am I Comparing?

Am I wanting to quit because I’m comparing my progress or results with others? I’ve repeated this quote I borrowed from my sister-in-law many times: “Comparison is the death of joy.” It can also be the death of progress and momentum. Correspondingly, bestselling author Greg McKeown says, “When we end our war on our body’s natural rhythms, when we let others pass us in the unwinnable race for the most achieved with the least rest, our lives gain texture, clarity and intention. We return to an effortless state.”

“When we end our war on our body’s natural rhythms, when we let others pass us in the unwinnable race for the most achieved with the least rest, our lives gain texture, clarity and intention. We return to an effortless state.”

  • Is This a Stormtrooper?

Borrowing another branch of wisdom from McKeown, ask yourself, “Is this a stormtrooper?” What’s the context? Growing up, McKeown loved Star Wars. After watching Return of the Jedi, he wanted a stormtrooper outfit. Anyhow, as an adult, he finally purchased one, and as he looked at his adult self in the mirror, he realized he didn’t want one all that badly after all. Having long outlived its relevance, the idea just hijacked space in his mind for many, many years.

We can carry these simple ideas, like the stormtrooper outfit, around until we let go, free our minds, and focus on what actually matters most. This decluttering of the "stormtroopers" helps alleviate the thought build-up that drives overwhelm, fatigue, poor decision-making, and procrastination, making us more susceptible to quitting things too soon. 

  • MVPs and MVAs — Has the idea proven it’s worth pursuing?

Not Most Valuable Player, but Minimum Viable Product and Minimum Viable Action. When I started Kosan Travel, before deciding to go deep into the business, we tested what Venture Capitalists and Angels refer to as a Minimum Viable Product — product with enough features to attract early-adopter customers and validate a product idea. This allows you to test whether your idea has viability in the market before deciding to bet the farm on it. The follow-through method involved Minimum Viable Action. What’s the simplest step I can take next? Don’t waste too much time, money or energy pursuing the full details (aka getting in the weeds) of your MVP until you have proof it has a chance at becoming a fruitful endeavour (note: Yes, you still must work hard to make sure you give your MVP a proper and fair market test). Quitting after you’ve tested an MVP (assuming you gave it a fair shot with the right audience) that didn’t pan out like it did when you dreamt up the idea, is a great example of knowing when to quit something. Inversely, it can tell you when an idea is also worth struggling for. (see point 10) 

  • Great is the Enemy of Good Enough

In keeping with the point above, allow your MVP (which by the way, can be a book draft, a movie concept, a business product — anything really) to be a bit “rough” in the early days, and not let perfection get in the way of getting it done. The first final draft of our film Raising Global Citizens wasn’t perfect. It wasn’t edited for audio or colour, and I just knew instinctively that there were holes in the story’s structure. That didn’t stop us from putting it through a circuit of film festivals. We were rejected by 19; however, the ones we did get in provided fantastic feedback with opportunities to improve the film while making valuable contacts and gaining some positive awareness along the way.

The job of a creative is to ship the work you create (get it out there), consistently. At least that’s what marketing guru Seth Godin says. And I tend to agree. From a spiritual perspective, it’s very Bhagavad Gita of him, in that we are entitled to the work but not the result or the work.

In Seth’s own words, “Shipping, because it (the work) doesn’t count if you don’t share it. Creative, because you’re not a cog in the system. You’re a creator, a problem solver, a generous leader who is making things better by producing a new way forward. Work, because it’s not a hobby. You might not get paid for it, not today, but you approach it as a professional. The muse is not the point, excuses are avoided, and the work is why you are here. Your work is too important to be left to how you feel today .” 

  • Sankofa

Our fears live almost ever-present in the stories we tell ourselves about how things are. “I can’t do this because _________________” I suspect you can fill in the blank with a plethora of reasons. Some excuses may be real or serious, but one must meditate on their origin before accepting their truth. An example:

“I want to quit.”


“Because the boss makes me feel small.”

“Why does what the boss says make me feel small?”

“Because I feel like I don’t belong here.”

“Why do I feel I don’t belong here?”

You see where I’m going with it. In these moments, we must practice Sankofa, from the Twi language of the Akan Tribe in Ghana meaning “to retrieve” (literally “go back and get”).

Behind every “what” there is a “why,” and when we understand the why, we understand the real reason driving what’s showing up in our consciousness as the story we’re telling ourselves about why we can't do something.

When we understand a problem that’s creating a desire to quit, we are essentially freed from having to fix it because, once we understand it, it no longer holds power over us. This is awareness. Not just awareness of what we are thinking, but why we are thinking it.

To borrow a metaphor from the author of the best-selling War of Art, Steven Pressfield says, “On the field of the Self stand a knight and a dragon. You are the knight. Resistance is the dragon. When we conquer our fears, we discover a boundless, bottomless, inexhaustible well of passion.”

We conquer that dragon through the action that follows our awareness and understanding why it’s breathing fire on us in the first place. 

  • Why Am I Doing This?

Does the spirit move you? Why?

This question is often overlooked yet correlates with the first two: “Why am I doing this? Do I love this thing (be it a job, a relationship, a place you live), or do I love what it provides me? Is this something I would do if I had the choice not to? Is the reason I’m doing it satisfactory to my soul? The trap we must try to avoid is doing things because they have become a habit, an obligation, or because we think we have no choice: someone told us it was required or the right thing to do.

Once a day, once a week, or once a year — whichever suits you — take the time to pause and ask yourself why you are doing something. Dig deep and uncover the real reason behind it. Why am I building this business? Why am I dating this person? Why am I spending time with these people? Why do I have this hobby? Why do I put my kids in so many activities?

Asking this question isn’t about over complicating the decisions we’ve already made tough enough. This is the simplest question we often have the hardest time asking and answering… “Why am I doing this?” A related question could be, “Why am I doing it this way.” There could be an easier or more efficient, productive or rewarding way of doing the same thing. What about the question, “What if I did the thing I wanted to do?” How often are we guilty of delaying or postponing the things we want to do (the things that give us the best answer to our WHY) until much later in our lives?

As Henry David Thoreau said, “The price of anything is the amount of life you exchange for it.” If it turns out you’re not willing to struggle for the thing you wanted, you don’t really want it. Move on.

  • What Is the Worst Thing That Can Happen and Am I Okay With That?

This life question dating back to somewhere between 121 CE and 180 CE, comes to us from the great philosopher and leader, Marcus Aurelius.

It is a simple, yet powerful, question with a related practice that helps us make key decisions about whether or not we should stay with a creative or entrepreneurial project. Answering the question truthfully for ourselves removes anxiety about the great unknown future. If we CAN be okay with the worst-case scenario, then what is there to worry about? If we can’t, then maybe we should re-think our next action.

This teaching, and many other stoic philosophy teachings, remain as relevant today. They can be found in Meditations by Marc Aurelius and The Obstacle is the Way by Ryan Holiday. 

  • Am I Willing to Struggle For This?

This question is a carryover from the first question. Generally speaking, nothing is usually as easy as it appears on the surface. To achieve success, happiness, physical fitness, and healthy, thriving relationships requires struggle. Let’s be clear, I’m specifically choosing the word struggle and not suffer as there is a world of difference between the two. Suffering usually means what we’re doing isn’t right for us and it’s time for a change, while struggling implies that there is resistance, but that resistance positively shapes us…not hurts us. We can struggle elegantly, gracefully, and with reverence.

So why does happiness have to be “struggled” for? Because, for a great many of us, happiness usually comes with the difficult committed work of letting go of expectations, fears, limiting beliefs, and concepts and becoming aware of who we are deep down inside. That journey can take a lifetime.

If you want to be a successful person, either as an entrepreneur or by climbing someone else’s corporate ladder, risk and sacrifice are part and parcel.

Successful relationships are born of time spent listening, working through differences of opinion, finding balance, releasing past pains and, often, choosing to keep this relationship over and over again.

Those who meditate and spend years in spiritual practice and contemplative reflection, battling their demons and egos along the way, are usually the ones who achieve self-actualization and freedom from suffering.

Those who spend the most time pushing themselves physically by lifting weights or running or swimming or climbing giant rock faces are the fittest.

As Henry David Thoreau said, “The price of anything is the amount of life you exchange for it.” If it turns out you’re not willing to struggle for the thing you wanted, you don’t really want it. Move on.

I think you get the idea. The point is, struggle is a basic component of our lives, and part of determining our success. And, by nature, struggle comes with great sacrifice. So, what are you willing to struggle for? 

  • Commitment and Opportunity

It’s not just what am I willing to struggle for, but what did I commit to? If quitting means breaking a promise or a deal, it’s VERY important to factor that in before you throw in the proverbial towel. If you’re at the point where you are having a “dark night of the soul” with your project, it’s not just the result you’re struggling with, it’s your word.

There is more than a fair share of nuance in this topic, which I won’t get into here. So, the net take away is be careful in calculating your commitment to things up front. Commitment is an important tenet of success, and so is cutting our losses and knowing when other opportunities are simply better for us. Therefore, when you’re assessing whether to continue something, have a clear idea of what you’d do instead. As Scott Youngs says, “Sometimes a project is hitting a rough patch, but it’s still the best idea you have of how you’ll reach your goals — you just need to push through.”

Not continuing with a creative or entrepreneurial project can also just mean putting it on hold. I personally don’t believe in totally abandoning an idea. Instead, I’ve created a FUTURE IDEAS note file on my phone and in a Google Drive Folder; they hold fully baked and very informal ideas I’d like to try at some point. This is also where ideas that didn’t work can live until such time that my personal situation or the market condition favor another look at it. 

  • Define Done

When I’m stuck in a business that’s struggling, or a project that needs to ship , I think about my long-time business partner Alex McAulay, who always says, “What are the conditions of satisfaction, and define what ‘done’ looks like.”

The light tinkering on your work  can make things worse. In the case of the film, it made it better. In the case of Kosan’s best-selling Go Travel Dress, it made the dress worse. When we first launched, we had a dress that people liked and it was good enough. We thought we could make it better, so we changed a bit here and a bit there and many of our customers thought the dress didn’t fit as well as the first one.

So, to end with a popular Steven Covey quote, “Begin with the end in mind,” and define when your project is done.

Original Raising Global Citizens Film Project started in 2008


With all that said, I’m brought back to our film. Throughout these many years we’ve worked on the film, not only was it one of the best ideas we’d had, but it was the one I was most passionate about; I felt that more opportunities could blossom out of, even if it wasn’t a smashing success. Time and again, we went through some or all of these questions, and time and again it felt right to keep going.

So, we stuck with it. And after all those misfires at film festivals, an entire (not to mention expensive) re-cut, and some initial disappointment with potential content distributors who don’t accept unsolicited film submissions, we’ve signed with an agent who believes in us and our project.

Needless to say, I’m glad we didn’t quit. It is not lost on me that the reason we didn’t probably had something to do with the inspiration of friends in Lebanon, and around the world, whose spirits inspired us to keep going, and whose stories we wanted to share.

Thanks for reading,

Be well!

After re-starting Raising Global Citizens Film Project in 2016

Stop Being Safe. Be Creative.
What Do Women Really Want in a Man? Here are the Top 5 Things Our Female Team Said: