Handling Naysayers When Taking a Leap of Faith

Sometimes, the naysayers really suck.

When pursuing anything new — particularly a startup — you will inevitably encounter psychological challenges. These challenges can be uncomfortable and may cause you to question whether you are really cut out to be an entrepreneur.

That said, some of the most psychologically difficult times come when you are about to start a startup. Some of those challenges are imposed by others — especially close family and friends — who cast doubt on our dreams. This is especially true if you are leaving a safe, secure job to become an entrepreneur.

So how do we approach this problem? How do we stoke our own enthusiasm and momentum for our goals while dealing with those naysayers shouting from the sidelines?

For the latest episode of The Power Of Bold, I discussed these issues with Tim Alison, the founder and CEO of Screw The Naysayers Productions. In his early 30s, Tim left his secure corporate job in Toronto to move with his family to a small fishing village in Nova Scotia.

You can find the episode on iTunes, Google Play, Spotify, or Stitcher.

By being bold and embracing action, Tim eventually started a multimillion-dollar educational software company. He now coaches entrepreneurs and wantrepreneurs on how they can build their businesses and create a life they love.

Like prior episodes, I’ve found it helpful to collect and share some of my favorite insights from the conversation. Those insights are below, but if you would like some more advice on leaving a secure corporate job to start a business, I would encourage you to listen to the whole episode.

Identify Your Values

Tim, like many young professionals, seemed to be on the fast-track to career success. In his late 20s, Tim was working in corporate sales and was racing up the corporate ladder.

By 27, Tim had a six-figure income. By 28, he was managing sales offices from Toronto to the east coast of the United States. Members of his sales team were ten to fifteen years older than him and Tim’s income kept rising.

Everything seemed great on the outside. But on the inside, Tim was struggling — at times, massively struggling.

Tim felt like he was following society’s playbook, yet he was miserable. Yes, he was being paid handsomely. But due to his work schedule, he wasn’t able to spend much time with his children. Eventually, he started abusing alcohol. Drinking a bottle of Pepto-Bismol every night didn’t cure his ever-present heartburn.

Things were not looking great.

Yet even though quitting seemed more and more attractive, he felt the tightening of the golden handcuffs. Tim had stock options in his company and didn’t want to leave them on the table. Along with that, he recognized that others would kill to have his job.

After about one year of agonizing whether to leave his job, Tim made his decision.

He decided to take a leap of faith.

In our conversation, Tim mentioned that he hit an infrastructure-rattling event. He needed to try something else because, in his words, he was either “going to be dead or divorced within the next five years. Maybe both.”

Along with this, Tim analyzed what really mattered to him. His list did not contain financial or material goals, but rather included things like spending time with my kids, being a present parent, and being around nature.

Ultimately, if you are in a job or career that you increasingly dislike (perhaps hate), one of two things will probably happen.

You may encounter an infrastructure-rattling event that may significantly affect your health. Your body will force you to do something else — and the consequences may not be pretty.

There is a much more pleasant alternative. You can sit down, determine what you truly value in life, and see if your current job or gig conflicts with your values. If you see a conflict, you need to do some more reflection. Think about whether you can solve the conflict at your current job or if you need to take more drastic action.

Ultimately, Tim chose the latter option. Your choice may be different.

But whatever your circumstances, it helps to sit down and take a look at things that you really care about. If you identify a conflict between those values and your current situation, you can’t sit back and be passive.

You should have a bias for rational, calculated action — whatever it is — to live according to your values. By doing this, you will be much happier, healthier, and in a better position to make more money in the long-term.

Delicately Handle the Naysayers

Once Tim was thinking of leaving his secure, well-paying job, he encountered resistance from those naysayers.

You’ve undoubtedly encountered them yourself. These are the people that tell you that your idea “will never work.

They may say “Well, if your idea is so great, why hasn’t anyone done it yet?

They may even be more upfront, saying “You’re simply not capable of pulling this off. You’re better off staying at your job and passing on that idea.”

Even today, we face naysayers when we’re about to take the leap and start a business. Naysayers are simply a part of life.

That said, Tim had it especially rough.

Tim left his job to become an entrepreneur in the late 1980s. At that time, entrepreneurship as a career was much less plausible than it is today. Not only that, Tim’s plan was to build his business in a rural fishing village rather than a large city with, presumably, more resources and talent.

Tim says his naysayers called him “every name in the book.” That said, he proceeded anyway and eventually created a multimillion-dollar educational software business.

If you want to take a risk in life or accomplish some large goal, there will be naysayers. There’s no doubt about it.

We all want to be liked. And it hurts to hear the negative opinions of others when we are trying to pursue our career goals.

Because of this, we need to have a game plan to deal with the naysayers.

To start, it’s important to identify the different type of naysayers. The first group includes the people described above. They are individuals who will simply cast doubt — sometimes significant doubt — on your goals and dreams. They won’t offer constructive criticism and will want to bring you down because of their own insecurities or doubts.

Luckily, it is easy to identify these types of naysayers. Often, it is in your best interest to ignore them.

There are other kinds of naysayers, however, who are deeply skeptical of your idea or plan, but aren’t simply shooting it down or disparaging it due to their own insecurities.

For instance, they may ask “What if they note a massive competitor, for instance, that is selling their product at half the cost that you intend to charge?”

In this situation, Tim recommends that you write down the criticisms and concerns. Ask yourself “Are they true?” And if so, “How can I mitigate that risk or challenge?

The second group of naysayers is much more constructive than the first group. That said, you ultimately want to construct a group of supportive, positive peers that will help you overcome the challenges within your entrepreneurial journey. The journey is hard enough: you want a group of optimistic peers rather than pessimistic peers.

This naturally leads to this question: what if a particular naysayer is someone I care deeply about?

This can be dicey. The biggest, non-constructive naysayer can be a close family member or a close friend. In that case, you may need to delicately shut down the conversation. You‘ll want to speak less about work and more about other topics.

Even if that close family member or friend believes they are looking out for your best interests, you need to avoid the negativity and focus on the positive. It may be painful, but doing this will maximize your chances of success.

Boldness Opens Doors

While Tim had this plan of becoming an entrepreneur, he wasn’t exactly sure of how he would build a growing, thriving business.

It’s like that Internet meme: take some step, then “?”, then profit.

There was not only deep uncertainty about his near-term career, but Tim was moving from the busyness of Toronto to the sleepy streets of a tiny Nova Scotian fishing village. Handling the culture shock, even though he had previously visited the village with his wife, would take time.

Having said all of that, Tim prioritized action.

He planted many seeds, testing his business ideas with local businesses and local government. As he was experimenting, Tim ran into a man named Roy who would later introduce him to a technology product on adult literacy.

While he had doubts about whether the product would sell in Canada, Tim acted. He ran with the product, made some modifications so that he could sell it in Canada, and eventually sold $10 million of that product, all while recruiting a team from his tiny fishing village.

It’s easy to be skeptical about the future if you are trying to create something new. And as discussed, those naysayers will come out of the woodwork and will try to keep you down.

But if you embrace boldness and embrace action, doors that you never envisioned will start to open. You just have to walk through those doors with the confidence that things will work out.

Granted, being bold isn’t about being reckless. Boldness involves taking smart, intelligent risks that maximize your chances of success.

It isn’t about sitting and contemplating the action you will take one day. It is about taking action now, seeing what works and doesn’t work, and iterating from there.

Boldness is about taking life by the horns. It’s about following your passions and dreams rather than simply settling for being “fine.”

The Beauty of the Small City

When hearing the phrase “high-growth startup,” it is easy to imagine a technology company with its headquarters in large cities on the east or west coasts. And granted, there are some advantages to building a startup in places like Silicon Valley or New York City.

That said, it’s not the only way to succeed.

Tim built a multimillion-dollar tech startup in a small city in Nova Scotia.

Tim leveraged several advantages of his location. First, a lower cost of living stretched his dollar and allowed him to invest more in his growing business — particularly by paying higher wages to his employees. Higher wages, along with Tim’s managerial style, led to more loyalty from those employees.

Tim was also able to find hidden talent, including a stellar technical support employee. This employee, who was thought to be incompetent by Tim’s partner corporations, eventually earned accolades and awards for his work. For his current work, Tim is able to leverage freelance platforms (like Upwork or Fiverr) to find some of the best talent in the world.

Last, but certainly not least, Tim was able to use his environment to improve his state of mind. When he needed some headspace, Tim could satisfy his passion for the outdoors by going on long hikes. By embracing the environment that he deliberately chose, he could return to work refreshed and ready to take on the day.

Therefore, if you want to start a business but are in a suburban or rural environment, rest assured that it can be done. It can also be done if you are living in a small or large city.

No matter where you live, take stock of the unique advantages of your hometown. From there, leverage those advantages to the maximum of your ability.

This Is Your Life

If you are unhappy with your current job and want to take the leap into entrepreneurship, you will, in all likelihood, come across naysayers. It can be easy to take those naysayers’ words seriously — especially if those words are from someone you love.

That said, life is short.

You have to live your own life — not your naysayers.
You have to live with any regret from foregone opportunities — not your naysayers.
You have to ask those dreaded “What if?” questions — not your naysayers.

Yes, the road to building a business is not easy. You will come across challenges that your naysayers may have even mentioned.

But stay true to yourself. Take bold, smart action when pursuing your dreams. And when you achieve your goals, don’t hold any grudges when the naysayers start knocking at your door.


Thanks for reading! Once again, you can access Tim’s interview on The Power Of Bold by visiting our page on iTunes, Google Play, Spotify, or Stitcher. If you’d like to read a full transcript of the episode, you can access the episode’s show notes here.

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