Is Entrepreneurship Right for You? What to Know Before You Start a Business
- Roger Pierce
- 2 hours ago
- 5 min read
Almost everyone knows someone who dreams of starting a business. Most never do it.
A Dartmouth study reveals that 70% of Americans say they want to work for themselves. Yet figures from the U.S. Bureau of Labor Statistics indicate only 6% of Americans are self-employed.
In Canada, while roughly half the population says they are considering entrepreneurship, startup activity has actually declined over the last two decades.
Some are held back by money. Others by fear. Many simply don't know what entrepreneurship is really like.
That uncertainty is what Roger Pierce explores in his new book, The Unsure Entrepreneur, and in a recent episode of The Unsure Entrepreneur Podcast, where Leigh Mitchell turns the mic around and interviews Roger about why he wrote it.
Leigh is the founder Women in Biz Network, host of the ChangeMaker Leader Podcast, and an entrepreneurship educator at York University and the University of Guelph Humber.
In the interview, Roger says his book is written for people who are thinking about starting a business but are not sure if they should.
Leigh understands that uncertainty firsthand. Growing up, her father owned a resort, and she witnessed the emotional and financial strain entrepreneurship placed on her family. That experience later shaped the cautious and deliberate way she approached business ownership — a story she shares in The Unsure Entrepreneur.
"I made a very conscious decision when I started my business that I would be more conservative about how much money I was willing to invest up front," Leigh says.
The decision before the business plan
In the interview, Roger says much of the advice out there aimed at entrepreneurs starts after the decision has already been made. It focuses on writing a business plan, finding customers, building a website, pricing the offer, and marketing the business.
Those things matter, but Roger argues there is an earlier and more important question: should you start a business at all?
“I wrote the book for people who are on the fence, unsure, thinking about it, considering entrepreneurship, and want answers before they take that leap."
It's a familiar place for many aspiring entrepreneurs.
They may have an idea they have carried around for years. They may imagine leaving their job, becoming their own boss, and having more control over their time. But they may also worry about money, failure, timing, family pressure, and whether they have the temperament to handle the uncertainty.
That hesitation is not necessarily a problem. It may be the beginning of a better decision.
In fact, Leigh says reading the book caused her to revisit her own entrepreneurial journey. "It got me going back to the drawing board and really thinking about some of the reasons why I got into business, what is keeping me there, and some of the challenges I still face to this day."
What changes when you become the boss
Roger talks about one of the first shocks for many new entrepreneurs is the sudden weight of responsibility. “The typical path to entrepreneurship is someone coming from working in a job," he says in the podcast.
In a job, there are systems and people around the employee, he explains. Someone else may handle payroll, fix the technology, manage the books, process invoices, or deal with the printer when it stops working. In a small business, all of that can land on the owner.
The transition can be jarring because a new entrepreneur is suddenly salesperson, marketer, bookkeeper, customer service representative, recruiter, strategist, and janitor.
Some people enjoy that level of control and variety. Others find it overwhelming. Neither reaction is wrong, but it is important to know which one is more likely to describe you.
For more insights about self-employment, subscribe to Roger's newsletter called Almost A Boss.
With all those new responsibilities and an endless to-do list, Leigh says it's quite common for entrepreneurs to get burnt out. "Burnout can happen in the early stages, during growth, or even when you're preparing to exit. We're never really at a stage where we aren't striving and achieving, and that can feel overwhelming."
The emotional risk is real
The emotional side of entrepreneurship is another theme in the episode. Business books often focus on financial risk but they do not capture the full experience.
Beyond money, Roger says he wants aspiring founders to know how entrepreneurship affects physical health, mental health, time, identity, confidence, relationships, and family life.
Emotional risk is largely overlooked — especially stress
Consider for example the stress an entrepreneur feels when money gets tight.
While an entrepreneur certainly feels ongoing pressure to make enough money to feed their own family, a business owner with employees has an added obligation. Employees must be paid first — and that responsibility can create a kind of stress many new entrepreneurs are not prepared for.
There is also the stress of not knowing if the business will achieve income targets for next month, the pressure of selling to customers when the owner maybe doesn't feel like doing sales that day, and the loneliness of making decisions.
None of that means entrepreneurship is a bad path, says Roger. It means the decision deserves respect.
Not all businesses carry the same risk
Leigh and Roger discuss how an entrepreneur's choice of business model can significantly impact the level of financial gain, stress, and personal risk they may face.
For example:
A service business is less expensive than starting up a retail store or factory. "Service businesses can be a good entry point for people who are more risk averse," says Leigh.
Starting a side business is less risky than quitting a job.
A solo consulting practice is less risky than hiring a team.
A home-based business is different from signing a commercial lease.
One of the key lessons in The Unsure Entrepreneur is that the best business for is not necessarily the one that sounds the most exciting or impressive. It's the one that aligns the founder's skills, goals, financial situation, family commitments, and tolerance for risk.
The rewards are real too
Still, the episode is not meant to discourage people from starting a business.
Entrepreneurship can create freedom, income, confidence, and control. It can give people the chance to build something that belongs to them.
“As an entrepreneur, you get to make all the decisions," says Roger. "Other benefits include freedom and flexibility. I mean, being able to go and watch your kid play baseball if you need to knock off early or take your kids to swimming lessons, to weave in your family life to your small business life, that is a true benefit.”
That may be one of the strongest arguments for entrepreneurship. Not freedom from work, but freedom to shape the work. There is a difference. Entrepreneurs work long hours, but they have greater control over when, where, and how that work gets done.
The goal is a better decision
Near the end of the interview, Leigh asks Roger whether he would still consider The Unsure Entrepreneur a success if someone read it and decided not to become an entrepreneur.
His answer is simple: absolutely.
"Not everyone should start a business," Roger says. "The important thing is understanding what entrepreneurship asks of you before you commit."
The world needs more entrepreneurs to dream, create, innovate, and lead. It also needs entrepreneurs who understand what they're getting into.
Leigh sums it up well. "Entrepreneurship is a great path, but it is not a casual decision. People often underestimate what is required. For those who are prepared, it can be incredibly rewarding," she says.
If you're thinking about starting a business, the advice is not to abandon the idea. It is to slow down long enough to ask better questions. Look at your money, skills, support system, family life, and appetite for uncertainty. Then decide.
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