Making friends with failure

This F-word is losing its stigma, as professionals learn how to turn a fail into future success.

Bruce Densmore, founder of Densmore Consulting Services Inc. in Halifax, recalls the first time he experienced failure as a would-be professional accountant in the early 1980s. And the second time. “The first time I tried the Atlantic School of Chartered Accountants tax course exams, I was very close to passing but fell just short. The second time I burned out from excessive study and ended up with a far lower mark and possibly the lowest mark in Atlantic Canada.”

Fortunately, a chance encounter with a friend pulled him out of his failure mode. “He told me, ‘There are people who are not as smart as you who are passing. You’re doing something wrong — figure it out and fix it.’ I got the tough love speech,” says Densmore. “I figured out this wasn’t random — there were patterns. Instead of brute-forcing the exam I took a much more systematic approach to preparing for it.”

After speaking with successful candidates about their exam prep, Densmore’s new study plan included reviewing five years of prior exams, creating an exam prediction model and using those old exams and other tax questions as his primary source. “I walked into the examination rested, confident and ready to destroy whatever they threw at me. I ended up with the second-highest mark in Atlantic Canada.”

That experience led him to his life’s work — helping future accountants who are struggling with their exams. As Densmore discovered, failing can sometimes be beneficial because it forces you to reassess the status quo, possibly take risks and come up with great solutions.

This positive view of failure is now catching on in the corporate world. Traditionally viewed as a shameful experience that should be avoided at all costs, failure is beginning to lose its stigma, thanks to a growing stack of academic research and high-profile cases that prove failure can lead to great success.

While research conducted in the 1970s supported the prevailing wisdom that people who fail once are more likely to fail again, a groundbreaking 1994 German study showed that people who are more action-oriented (in other words, more likely to take any kind of specific action rather than simply ruminate) succeed more easily in the future.

More recently, psychology professors at the University of Kent in Britain published a paper on recovering from failure. They found that students who experienced a small failure or setback but subsequently put a positive spin on the ordeal — accepting it and laughing about it — bounced back more easily than those who used other coping mechanisms such as denial, venting or self-blame.

Another factor contributing to the shifting attitudes on failure is the glorification of individuals who have overcome it. Indeed, some of the greatest business success stories of our generation are of failures gone right. Steve Jobs, for example, was ousted from Apple in 1985 but returned years later to turn the company around, while J.K. Rowling, the highly successful author of the Harry Potter series, had her first book turned down by 12 publishers before landing a deal. Moreover, these failures on the road to success became a kind of badge of honour indicating tenacity, hard work and perseverance. As Jobs famously said, “Sometimes when you innovate, you make mistakes. It is best to admit them quickly, and get on with improving your other innovations.”

The modern failure movement, however, really took off in 2008, when charitable organization Engineers Without Borders Canada (EWB) created a failure report to examine and learn from its mistakes. Each year, its engineers catalogue their failures — everything from poor performance in a new position to underestimating funding needs. When EWB tried to bolster local farmers’ groups in Burkina Faso, for example, it failed to develop an appropriate marketing strategy. EWB has even gone so far as to establish a website,, where other organizations can share — and hopefully learn from — their failures.

Around the same time as EWB began its failure reporting, the tech industry embraced failure as a necessary part of growth and discovery, says Ashley Good, founder of Toronto-based Fail Forward, which helps organizations learn from their missteps and create room to try new things. “In Silicon Valley, they’ve promoted a lot of fail-fast mantras, which allow you to test quickly and cheaply and learn from what works and what doesn’t and move on.”

Failure is so ingrained in the tech world that in 2009 the notion spawned FailCon, an annual conference in San Francisco for startup founders to study their own and others’ failures and improve upon outcomes. Ironically, it was such a huge success that it led to similar events around the world, including France, Spain, Brazil and Israel.

Want to join the ranks of the failure movement? Here’s how you can capitalize on your own catastrophes and embrace the benefits of failure.


The first step in dealing with failure is, of course, admitting it. But that’s a lot harder than it sounds. Failure on a personal level can be embarrassing and sometimes even soul-destroying. Nava Jakubovicz, a career and educational coach in Toronto, says you have to give yourself time to deal with the pain of failure, whether it’s a setback at work, being fired or laid off. “It can be a kind of grieving process. People who give themselves time to feel upset, figure out what to take from it and speak about what they’ve learned will move forward more quickly,” says Jakubovicz.

That was the case for Jean MacKinnon, CPA, CMA, who bounced back from a bad situation with a family-run distribution business in 2001, when disputes over succession and the direction of the company became intolerable. “It reached a level of frustration where I quit. Dealing with it was a lot like the seven stages of grief — it was like a death.”

But after MacKinnon got through the full range of painful emotions, she was able to view the ordeal as a new beginning. Recently, she started her own firm, Blue Sky Governance Consulting Inc. in Dundas, Ont., and has found greater job satisfaction. “I’m stronger for it and I’m happier,” she says.

Jakubovicz offers the following suggestions to move you through the grief of failure:

  • Acknowledge your feelings of shock, anger, sadness and disbelief — they’re real.
  • Talk with a trusted friend, family member or counsellor who can just listen; be present in the moment; feel your feelings.
  • Make a list of your character strengths and skills, and write out stories demonstrating your accomplishments. “This exercise alone will help begin rebooting your confidence,” says Jakubovicz.
  • Don’t blame others, even if there was nothing you could have done to prevent the setback. Faulting others keeps you focused on the past, rather than thinking about how to move forward.
  • Don’t blame yourself either, even if you could have done something to keep from failing. Instead, look for lessons learned and how you can grow from this setback.

It’s also important to look critically at what you’re doing, rather than criticize yourself as a person, says Densmore. In his dealings with students, for example, he tries to pinpoint whether their difficulties stem from unbalanced study, poor time management or not winding down properly after studying. “We tell experienced writers they’ve got the ability; they’re just doing something wrong,” he says.


One of the least examined failures companies make is “opportunity failure” — or not taking a chance, says Good. To become more comfortable with risk and the fear of failing, she advises setting a goal of simply trying something risky, even if you think there’s a good chance of a negative outcome. That way you’re rewarding yourself for taking the chance and not the outright success. “The willingness to continue to change, taking that feedback along the way, helps you have small technical failures rather than big operational failures that are harder to get up from,” she says.

MacKinnon agrees that having had an opportunity to recover from a setback has made her more accepting of risk and potential failures. “I think I’m willing to take reasonable chances more than other people because they’re so locked into that fear of failure,” she says. “They’ve never had the opportunity to say it’s OK to fail. If you do everything perfectly, which we know we don’t, then nothing can improve. It’s like a muscle you become stronger for using.”

Ananth Koovappady, CPA, CMA, a franchisee with Instant Imprints in Mississauga, Ont., is a firm believer in embracing risk, even when it takes him out of his comfort zone. He was working for a large multi-business conglomerate in India when he decided to quit and head for Canada, where he landed a finance job in four months — a major risk that paid off. Years later, when his employer was acquired by a much larger US company and offered him a buyout package or a chance to move to the US in a lesser job, he risked it all again.

After researching for about 10 months, he purchased the printing franchise. “I knew I was going from finance to sales and marketing, which was very different from what I’d done. I still remember doing my cold calls and getting the door slammed in my face. I would ask myself what the heck I was doing,” he recalls. “But with each rejection I learned something new. Three years down the road I may not be an absolute salesperson like normal salespeople are, but I’m not afraid to barge into offices or pick up the phone and cold call people, which I do at least two hours a day.”


Astronauts, such as Canada’s Chris Hadfield, habitually anticipate failure and prepare a plan of action so they have the skills to deal with potential problems when they occur. “We practise things going wrong all the time,” Hadfield told a TED Talk audience, adding that when he started flying in the space shuttle, the odds of a catastrophic event were one in 38. “One of the things we say in the cockpit all the time is, what’s the next thing that’s going to kill us? Let’s focus on that and how we can keep it from happening or how to react when it does happen and then let’s go on to the next thing.”

Most failures in the business world don’t involve life-and death stakes, but the process of mapping out possible failures and drafting a plan of action for each scenario is sound risk management, says UK accountant and University of Oxford MBA student Michael Tefula, whose book Graduate Entrepreneurship: How to Start Your Business After University will be published later this year. “To find these failure points, research how other people fared on a particular venture or project,” he says. “Don’t look for just the success stories either. Seek out failure stories too. This will give you a richer understanding of your chances and help you craft a more intelligent strategy.”

Koovappady, on the other hand, chooses to visualize success rather than failure. “I play a bunch of self-affirmation tapes every night before I go to sleep. That’s always worked for me in life.”


Even if failure can be viewed as a positive, a surfeit of setbacks can be counterproductive.

“Too much failure can damage confidence because a lot of self-belief comes from past successes,” says Tefula. But he’s quick to qualify that repeated failures are less harmful for those who have the wherewithal to persevere. “This could be mental or even financial. For instance, if a person has a significant amount of cash savings they can continually invest in their business development and survive a few failures without being wiped out financially.”

Good agrees that sometimes failure isn’t just an obstacle to overcome, but a true barrier that should be heeded. If you’ve invested a certain amount of time and not seen any return or indicators that something might be profitable, you have to stop, she says. “If you draw your risk line before you start, it leaves you less vulnerable to a big failure.”

“We always read about the entrepreneur who failed multiple times before winning big. What we don’t read about is the entrepreneur who failed multiple times and got wiped out,” says Tefula. “Not sharing this narrative — however uninspiring it might be — deprives us of other equally worthwhile lessons and contributes to a more laid-back approach toward risk-taking.”

In most cases, however, once you get past the hurt, a failure will likely make you stronger, says Good. “The greatest failure is not to get up. It’s easy for me to say but it’s incredibly hard to do.”

As Prime Minister Justin Trudeau said in a 60 Minutes profile that aired earlier this year, recalling his famed 2012 boxing match with Senator Patrick Brazeau, the recovery is more important than the knockdown:

“People think boxing is all about how hard you can hit your opponent. It’s not. Boxing is about how hard a hit you can take and keep going. That ultimately is much more the measure of a person than someone who says, ‘Oh, I’ve never been knocked down,’ or ‘I’ve never been punched in the face.’ Well, you know what? Maybe you should have. You might learn a few things about yourself.”


The language of failure         

While failure may be viewed more positively these days, the terminology surrounding it still makes some people squirm. Words such as obstacle, challenge, stumbling block or lack of success can pack an emotional wallop when they’re used to describe failure.

That’s why exam-prep consultant Bruce Densmore works with students to change their vocabulary in regard to failure. For example, he uses the phrase “experienced writer” to refer to those who sat for the exam and failed — and the distinction isn’t simply semantic in his view.

“Experienced writers actually have an advantage over first-time writers because they’ve been through the process. They’re advantaged, not disadvantaged. It’s positive as opposed to negative,” he says.