Just last week I was on Zillow looking at properties in the Northwest. Dreaming might be another word for it. My wife and I often talk about a time where we could live off the land. A remote place that could bring us back into another century. An escape from the speed of life and a place that would allow us to find our wild.

There it was. A 40-acre ranch nestled in the mountains of Montana. A fully functioning farm with everything we needed to make that dream a reality. My heart started beating quicker. My mind began to race with questions about feasibility and options.

That next morning, I’m on a call with the realtor. A hundred questions and answers that bring me even deeper. I’m looking at flights and having detailed conversations with those around me. My vision for the years in front of us begin to change. Everything is different and it feels amazing.

But then it hit me… This was an incredible dream, but not for us. At least not right now.


You see, dreams can be as addicting as heroin. And as lethal, too.



They can seduce us into a vision of a more desirable future. A place where life seems easier and more fulfilling. A place where problems go away, laughter increases, and money becomes easy.

As entrepreneurs, dreaming is a critical part of our careers. It’s the fuel to move us from one season to the next. But the quickest way to fail badly is to dream poorly. Not every dream is a good dream. The ability to discern the difference between the two will save you from the immersion in needless distractions simply stealing time from what’s truly realistic.



Those who don’t manage their dreams well will always work for those who do.



They key is to see the warning signs early. To hedge yourself against time lost and emotion spent. Below I have identified 4 critical indicators of a dream you shouldn’t be chasing.

1. You’re giving up what you want most for what you want now

Pursuing a dream before you pursue a plan often leaves people with a life they never intended. Before you fall in love with an idea, spend time painting the big picture. For my wife and I, it’s always been in the form of a five-year plan. It’s built of three simple questions.

  1. In five years, where will we live and why?
  2. Outside of family, what will be our chief focus?
  3. What needs to happen between now and then?

Without a plan, a dream can disguise itself as a shortcut when in reality, it’s a detour. The plan is the banks that your dream river flows. It’s the vehicle that takes you from one season of your life to the next. If we’re not careful, our unplanned dreams of the present can steal your planned dream of the future.

Critical Questions: Is your dream or idea sacrificing the big picture? Or maybe the timing isn’t right. Are you trying to force your river to go left 300 miles before it’s natural curve? Take a moment today to answer these questions.

2. You’re scratching someone else’s itch to relieve the pain

The romance of Silicon Valley start-ups making instant millions has certainly set high expectations for dreamers in the past 10-15 years. It’s given dreamers a false sense of reality and made something very complex appear simple.

A few years ago, I wanted to start a boutique hotel. In common entrepreneurial fashion, I approached the idea with pride. “I can figure this out”, I told everyone. It wasn’t until 90 days into the discovery phase that I realized the idea I was so infatuated with, was a dream for someone with more experience in hospitality to take on.


Knowing where your good is great. But knowing where you’re bad is even better.


The hotel itch wasn’t mine to scratch. I was a naive outsider under-simplifying a dream in an area that was over my head. Sadly, I see this happen all the time. People dreaming about apps with no web development background or those chasing down restaurant ideas simply because they love food.

By no means am I saying you can’t chase a dream or start an idea in an industry you’re not familiar with; however, people are typically more successful when they follow ideas which align with their experience. A parent inventing a new children’s product, a beer enthusiast opening a brewery, or a realtor starting a home construction company.

Critical Questions: Is your dream directly in your wheelhouse? Or are you sailing uncharted waters? Remember, it’s okay to be unfamiliar, just be sure you’re solving your problems, not someone else’s.