Financial Poise

Does It Pay To Pursue Your Dream of Starting a Business?

Throughout childhood, we all dream about what we want to be when we grow up. We imagine life as a full-blown adult, envisioning wild success and abundant comfort.

Yet by the time we reach adulthood, an onslaught of obligations and bills has mixed in with reality, painting a far less glamorous picture. Many of us eventually settle for simple, secure, and stable careers instead of striving for more. This is especially true for those of us who aspired to be entrepreneurs with our own businesses.

The Statistics on Giving Up Your Dreams

  • 72% of workers who aren’t working in their dream job regret it, and given the chance, 61% would trade in their current job for their dream job.
  • 61% of workers have an idea for starting a business, but 92% never follow through with it.
  • In contrast, 92% of entrepreneurs have no regrets about starting their business, and 45% of entrepreneurs started their business to escape the 9-to-5 grind.

Pursuing your dreams isn’t easy. Oftentimes, there are very good reasons why more of us don’t. However, if there is a part of you that still hopes to recapture some of your childhood motivation, then the following considerations may help you decide whether it’s time for you to chase after your dreams.

Calculating the Cost of Dream Pursuit and Diversion

At every turn, entrepreneurs are told to be ‘realistic.’ Ambitions are dismissed as the stuff of daydreams. Young professionals are encouraged to pursue steady income and benefits above all else. Discussions about uncertainty focus on downside risks instead of upside potential.

Launching a startup can be risky, but not pursuing your dreams comes at a cost, too. By understanding the advantages and risks involved with pursuing your dreams, you’ll gain perspective on whether you’re in a position to make a move.

Money

Financial concerns rank among the top reasons why would-be entrepreneurs put off pursuing their dreams. According to a 2021 Freshbooks study:

  • 35% of aspiring entrepreneurs fear losing consistent income.
  • 28% worry about not having enough capital or being overwhelmed by debt.
  • 27% are scared they will make less as a business owner than they do as an employee.
  • 20% have concerns about sacrificing their health benefits.

Despite these concerns, entrepreneurship also offers unlimited financial upside. Employees get paid for defined work in a specific period of time and at a set rate. Performance incentives like bonuses and commissions are usually percentages or dollar amounts relative to someone else’s measuring stick, and they may be capped at a certain level.

Those who own their business make money based on actual performance. You make money when your business makes money, which brings its own risks but also uncapped rewards.

Time

We’ve heard it before. Time is money. Money is time.

However, when considering pursuing your dreams, time takes on a different level of significance. Small business owners work twice as many hours on average as their employed counterparts, with 33% working more than 50 hours a week and 25% working more than 60 hours. Demands on your time will be especially high during the earliest days of your business.

Even so, entrepreneurs frequently cite time and flexibility as part of why they launched a business in the first place. You get to choose when, where, and for how long you work on any given day. This matters because the value of time is not uniform. An hour spent cleaning the office windows, for instance, is not as valuable as the hour spent at your kid’s soccer game.

Time also matters in the context of when you get started. The longer you delay pursuing your dreams, the less time your dreams have to be realized and generate returns. Putting off an investment in your entrepreneurial dreams yields the same kinds of results as delaying investing for retirement: diminished returns, or the time cost of money.

This cost cuts both ways. Innovators may also find time to be on their side. Despite private equity’s love affair with disruption, ‘first movers’ can put themselves at significant risk of being squashed by larger, better-capitalized, and more nimble brands.

Happiness and Health

All the money in the world doesn’t matter if you’re miserable. Happiness is where pursuing your dreams yields the highest dividends.

This doesn’t mean that entrepreneurs won’t face challenges to their happiness and health. The stress of running a business can take a significant toll on your mental health. Entrepreneurs, like everyone else, must proactively safeguard their well-being.

How To Start Pursuing Your Dreams

Let’s say you’ve done the math, and you conclude that starting your own business makes the most sense. Time to put rubber on the road, right?

That’s easier said than done. None of us have a magic genie capable of delivering our dreams with a bob of their head. Pursuing your dreams successfully requires thoughtful, measured preparation and action.

Step One: Define Your Dreams

We’ve all dreamt of becoming titans of industry, silver-screen starlets, scientific trailblazers, or athletic legends. The specifics on how any of that comes to pass often take a backseat to aspirations of grandeur.

In a business context, our dreams need to be more concrete. Maybe you’ve always wanted to open your own restaurant. Perhaps you’d like to start selling the paintings you regularly make. You might hope to launch your own medical practice. These dreams necessarily have more definition than the usual flights of fancy.

Fully wrapping your mind around the details of exactly what you want to achieve is a useful exercise when pursuing your dreams. They act as our North Star, a compass to help guide us through all the tough decisions we must make in the short term.

Step Two: Establish Goals

Once you’ve crystalized your dreams, it’s time to chart a course on how to get there. Even with clear definition, dreams are still just ideas. Planning is how you make them a reality.

Identify key milestones and set goals to help you get there. The best approach to goal-setting is the SMART approach, where your goals must be ‘Specific, Measurable, Achievable, Relevant, and Timely.’ This makes achieving your goals easier, which in turn makes realizing your dreams more likely.

Step Three: Measure, Measure, Measure

Your measurable goals need to actually be measured for them to provide value.

Tracking your progress serves several purposes:

  • It provides visibility on the pace of advancement, allowing you to identify and address bottlenecks.
  • It enables you to better manage costs and risks over time.
  • It helps you better manage expectations among stakeholders, service providers, and employees.
  • It can offer motivation as you see how far you’ve come.

However, entrepreneurs must carefully parse this data. The point of measuring progress is not to discourage you based on previous choices but to inform your future decisions.

Is Pursuing Your Dreams Worth It?

The answer to this depends entirely on you and the dream in question. Many variables will influence your perspective. You may wrestle with the costs and benefits as you try to make up your mind.

However, addressing this complexity in decision-making is a crucial challenge for the aspiring entrepreneur. After all, your choice will have massive consequences for you and those you love. Entrepreneurship is about more than building a business. It’s about building an ideal life. Deciding whether to pursue your dreams is perhaps one of the most important choices you could make in your life, and it’s crucial to approach it thoughtfully and strategically.


We think you’ll also like:

  1. 7 Steps for Building a Small Business Brand Strategy
  2. Startup Business Tips from Industry Leaders
  3. 10 Reasons Start-ups Fail

[Editors’ Note: To learn more about this and related topics, you may want to attend the following on-demand webinars (which you can view at your leisure, and each includes a comprehensive customer PowerPoint about the topic):

  1. Turning an Idea or Product Into a Business
  2. What Every Founder/Entrepreneur Must Know
  3. The Sales, Marketing, Advertising & Publicity Bootcamp

This article was originally published on May 7, 2023. This article was most recently updated by the Financial Poise Editors.]

©2025. DailyDACTM, LLC d/b/a/ Financial PoiseTM. This article is subject to the disclaimers found here.

Share this page:

About Tom Kirby

Tom Kirby is the founder of Chicago-based file sharing service PrepDD. Before that he was Vice President of Business Strategy and Director of Finance and Operation for VIN-specific auto marketing technology company LotLinx, also of Chicago. Share this page:

Read Full Bio »

Follow Tom Kirby on: