Financial Poise

Does It Pay to Pursue Your Dreams?

Throughout childhood, we 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. 

But by the time we get there, an onslaught of obligations and bills mix with reality to paint a decidedly less glamorous picture. We settle for simple, secure, and stable careers instead of striving for more. This is especially true when talking about entrepreneurship

Over 74% of professionals regret not pursuing their dreams, with 92% of those who do falling short of their goals. If you hope to land on the other side of these statistics and recapture some of that childhood motivation, start here.

Calculating the Cost of Dream Pursuit and Diversion

At every turn, entrepreneurs are told to be “realistic.” Ambitions get dismissed as the stuff of daydreams. Young professionals get 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.


Financial concerns rank as some of the top reasons would-be entrepreneurs put off pursuing their dreams. According to a 2019 Freshbooks study:

  • 34% 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 

But entrepreneurship also offers unlimited financial upside. Employees get paid for defined work in a specific period of time at a set rate. Performance incentives like bonuses and commissions usually take the shape of certain percent or dollar amounts relative to someone else’s measuring stick and may be capped at a certain level. 

Those who own their own businesses make money based on actual performance. You make money when your business makes money. Period. As a result, entrepreneurs make an average of 50% more than their employed counterparts. 


Yes, we’ve heard it before. Time is money. Money is time. We get it.

But 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 on cleaning the office windows, for instance, is likely 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 get realized and generate returns. Putting off an investment in your own business dreams yields the same kinds of results as delaying investing for retirement: diminished returns, or the “time cost of money.”

But this cuts both ways. Innovators may find time on their side. Despite private equity’s love affair with the notion of disruption, “first movers” 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. This is where pursuing your dreams yields the highest dividends. Consider:

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.

What Pursuing Your Dreams Looks Like in Practice

Let’s say you’ve done the math. On balance, you think 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 has 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

Dreams reflect desire. We see ourselves as titans of industry, silver-screen starlets, scientific trailblazers, athletic legends. Details on how any of that comes to pass take a backseat to frothy visions of grandeur.

In a business context, dreams get a little more concrete. Maybe you’ve always wanted to open your own restaurant. Perhaps you’d like to start actually selling the paintings you regularly make. You might hope to launch your own medical practice. In any case, that dream necessarily has more definition than the usual flights of fancy.

Fully wrapping your mind around the details, though, proves a useful exercise when pursuing your dreams. They act as our North Star, serving as 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 ideas. Planning is how you make them a reality.

Identify key milestones and set goals on how to get there. The best approach is a SMART one – meaning setting Specific, Measurable, Achievable, Relevant, and Timely goals. This makes achieving your goals easier, which in turn makes realizing your dreams more likely.

Step Three: Measure, Measure, Measure

Those goals you made sure were measurable? You need to actually do the measuring for them to provide value.

Tracking your progress serves several purposes:

  • It provides visibility into the pace of advancement, allowing you to identify and address bottlenecks. 
  • It allows 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.

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

Is Pursuing Your Dreams Worth It?

The answer to that question 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.

But this complexity benefits the would-be 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 a life. Pursuing your dreams allows you to shape that life into something that would bring a smile to the face of your younger self.

Interested in learning more about how to supercharge your business? Check out our Startup/Small Business Webinar Series on demand. You can view the recordings at your leisure, and each comes with a slide deck for later reference. Topics include:

  • The Basics of Forming a Business
  • The Ins and Outs of Raising Capital
  • Essential Lessons for Founders

For more information about our on-demand webinar series, click here.

This is an updated version of an article from 2020. ©2023. DailyDACTM, LLC d/b/a/ Financial PoiseTM. This article is subject to the disclaimers found here.

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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:

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