Human nature tends to take us down the path of safety. The path of the “tried and true”. A large number of people will live their life without ever stepping out of their comfort zone. They will never test themselves, take a risk and will continue to flow with what society expects.


Folks will say “Retiring Early is just a dream. I’d never be able to pull that off.”  Now, that thought process already has them defeated. They have just accepted it as a fact. In their reality that is now a hard and fast “rule”. They’ll be working to age 65 and possibly/probably beyond.

The hardest part of the battle is truly fought in the six inches between your ears.

As humans, we’re really good at putting obstacles in front of our dreams and goals. We’ll accept things as they are and defend missed opportunities as “they just weren’t meant to be” instead of working hard to make those dreams and goals a reality.

Let’s check out 5 obstacles that may be stopping you from Retiring Early 


You keep telling yourself that you want to but fear is holding you back.  Fear of the unknown, fear of running out of money, fear that you’ll disappoint someone, fear that you’ll be bored, etc.  In your mind, you might be thinking that you’re taking a huge leap into early retirement without a safety net.  Well guess what? Your first safety net is the plan you put into place.  However, if doesn’t work out for you, an additional safety net is that you can always return to working full time or part time in the field you came from.  You’re not walking across a tight rope over Time Square without a safety net where one mistake and you’re dead.  Determine what your fears are and put into place safety nets. Learn yourself and then build the fear-blockers! This is part of your planning process and a good plan solves for the unknowns while quelling fear. 



I created the DIAL into Retirement process which stands for Debt, Income, Assets and Lifestyle.  When you get these four items in sync, you can retire at any age. You’ve heard me say many times that sitting down with a financial advisor shouldn’t be a confusing discussion. You shouldn’t have to feel like you are following rocket science to get a grasp of your financial outlook. The DIAL system is simplicity at its best. By attending to each of the four parts of the DIAL, you get simple clarity, know what action to take to improve, and <click> the DIAL unlocks and provides your path to freedom.



Most people will be excited about your retiring early plan but don’t be surprised if some “friends” and family aren’t too supportive of your plan. In fact, it saddens me to say it, but you should probably expect some not to be. For some it is simply inconceivable to think outside of the frame work society has established.  Other times the negative comments might come from a jealous or selfish standpoint.  Don’t get distracted trying to prove things to others.

Stay focused on your plan and don’t let the needs and wants of others keep you from your dreams.

I have also seen grown children alter their parent’s retirement plans because they used their  financials as their safety net for their risks and wants. Do not let this happen to you! Of course we all want to make sure our kids are alright in the world, and of course as loving parents we often want to take note of their concerns and needs. But at the end of the day, this is your life and your plans.



Lifestyle is the true secret to retiring early. Many folks don’t realize that making some basic changes to the way you live and spend can dramatically improve your plans on retiring earlier. This can be troublesome for some folks who want that high life but also want to retire early, but perhaps don’t have the resources to do so. “I don’t want to give up my new BMW, big house and country club membership.” Well, I won’t sugar-coat it; you may need to keep on working to pay for all of that stuff.  The more frugal you live, the better the chance you’ll pull off a successful early retirement. Yes, there might be some sacrifices along the way when you retire at 50 versus 65 but it comes down to what is pulling you? Your Freedom? or Your Stuff?



Start with a plan. This is often seen as a daunting task and will often overwhelm people into putting it off. If this is you, start with the fun stuff.  How do you see life in retirement? Travel? Hobbies?  Relocating? Get excited and this will get you motivated. Have you ever noticed how different a task feels after you are already in motion – or even after just getting started? It’s the same here.  So get started on a plan!  Whether you seek out my help or your financial advisor, it’s time to get your plan developed so you can put it into motion. Sure, it might take a few years to get it all tidy and nice for your exit from the traditional working world, but that certainly beats working for another ten or fifteen years doesn’t it? 


When you start eliminating the obstacles in front of you, you’ll have a clearer path to seizing your freedom. Need help clearing the path?  This is why I’m an expert in helping people plan for both their lifestyle and financial retirement goals.  Think of me as your jungle guide, hacking away all the brush and clearing your path with you.

I offer a free 30-minute conversation to discuss your plans and see if I can help you. Drop me a line and we can chat.

Live free my friends