Chasing Your Dreams Doesn’t Have to be Reckless

I’m not sure where this all started but for some reason I feel like “chasing your dreams” has taken on new meaning.  When I was a kid growing up in the 80s I was always encouraged to chase my dreams.  I would be told “you can be anything you want to be.”  Now, that’s a good thing.  And I think that in general the youths of today are encouraged in a similar way.  But there’s something different about the way chasing your dreams is being marketed as we get old.  In particular, in this new time period of people wanting to become entrepreneurs.  It’s a mindset that I think people should  be extremely careful with.  Having been an entrepreneur for the last 15 years I can tell you that there are plenty of people you should not be listening to.  In particular, the people who are encouraging the chasing of dreams at too huge a cost.

For some reason people think chasing their dreams means having to leave their jobs.  Sometimes they think it means having to “risk it all.”  Leaving your job is fine but do you have a plan?  Do you have money to keep you afloat while you are chasing this dream of yours?  Do you really have to be buried in a ditch somewhere and kicked down by life 6,000 times before it’s time to chase your dreams?  Hell no.  And guess what?  You shouldn’t pursue your dreams in this way.  It’s completely foolish and reckless.  And often times it’s unnecessary.  Chasing your dreams should be a strategic, patient, and measured endeavor. Let’s take a look at how one might approach this:


If you truly want to go after something you need to assess whether or not you’re in a position to.  Don’t get me wrong.  Everyone has their own risk tolerance.  Some people are in fact willing to give it all up to chase their dreams but that’s not the kind of people I’m speaking to here.  Personally I don’t think it’s wise to do anything rash.  So let’s use an example.  Let’s say you have a job that you don’t like and you want to pursue starting your own business.  This is a position that plenty of people are faced with in the real world.  But are you prepared for it?  What does prepared mean exactly?  Have you asked yourself these questions?

  • Do you have enough money for 6 months to a year to push the business?
  • Do you have enough time to start this business and keep your job?
  • Will this money cover your life AND business expenses?
  • Are you mentally prepared for it?
  • Have you researched what you’re going into enough?
  • Have you talked to other people in the same business you’d like to start?
  • What’s your plan if it doesn’t work out?

These are only a few of the important questions you need to be asking yourself.  The point of the matter is that you truly need to define where you are and deduce whether or not where you are now is a good enough position to get you started on your journey to where you want to go.

Action Plan

Let’s say you’ve made an assessment on exactly where you are and you’ve decided that you’re ready to go after your dream.  What’s next?  You’re never going to make it without some sort of action plan.  I’m not saying you need an elaborate business plan with numbers and projections.  Perhaps you would need something like that if you were going after investors but that’s not really my game.  My game is just “going after something.”  And the best way to go after something is to start.  However, even I know that simply starting does require at least minimal planning.  And by planning I mean allocating time and resources to whatever your new project or dream might be. Here are some questions you might think to ask yourself?

  • What will my hours be?  Is this a moonlighting thing?  Am I quitting my job entirely (see first questions and make sure you have enough money)
  • What are my financial goals?  I.e. what do you hope to be earning within a year
  • What am I actually doing each day?  Have you created a calendar for yourself?  Do you know what your daily tasks are going to be?

I’m not as concerned with the “what” as I am the promise of “doing the things each day” because as your business evolves so too will the “what you do.”  You may find that things you were doing in months 1-6 can be outsourced.  But I will say this:  You 100% have to stick to a particular routine.  You need to know that “I’m making X amount of calls per day.”  You need to say to yourself, I’m going to hit 1 sale per day at the end of 4 months and if you’re not there you need to assess why.  The first year of a business is about the DOING.  Get into that habit above anything else.  Results should follow.

Rinse and Repeat

Chasing your dreams doesn’t have to be a one time thing.  It can be multiple dreams and at multiple times.  Once you learn the process it becomes easier to repeat the process.  In other words, dreams are nothing more than goals.  However, I would throw caution into chasing too many dreams at once.  Just because I said multiple times doesn’t mean that you should be multi-tasking with dream chasing.  It’s probably best to go after your “main” dream for as long as it takes to either achieve it or you decide it’s not worth the effort.  Once you achieve said dream,  you’ve got yourself a great framework to work off of.  Build the framework first.  Then you can take the next step of rinsing and repeating.  Get after it!

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