A Roadmap For Following Your Heart

"While there are times when making decisions solely based on what you should do is totally appropriate, there are also times when it is not, times when living your life means abandoning what you should do to follow your heart."

Let’s start out with full disclosure. My academic, professional, and geographic history all attest to the fact that I am a bit of a wanderer.

Not the aimless type. I have always had plans.

But the poster child for staying in the same place and doing the same thing for years on end, I am not. I am a follow-my-heart-make-calculated-risks kind of guy.

Now that we have established that, we should also establish the fact that despite knowing this about myself, I have often struggled with accepting it. I have beaten myself up countless times over desires to live in new places, try new things, over leaving successful and well paying jobs to follow my heart. I have spent much of my adult life pining over the life I “should” be living instead of enjoying the life I felt compelled to lead. It did not matter that every one of those “non traditional” decisions ended up leading to a happier, healthier, more prosperous life.

This internal tug of war became a routine game until one day I found myself sitting in a therapist's office lamenting over all of the ways that I should be living my life if only my pesky makeup would get out of the way. After I droned on for five solid minutes my therapist looked at me and calmly said..

“Why are you always should’ing on yourself? You’re always worried about what you SHOULD be doing. What do you WANT to do?”

Why only focusing on what you should do with your life is a problem

Should is a word typically used to define an obligation, duty or expectation. This is not all bad as there are a number of things that we should want and expect. I should expect my dog not to attempt to eat out of the trashcan 5 minutes after he ate dinner. I should expect my friends and family to offer me love and support when I need it most. I also should expect most people to be moderately decent human beings.

The challenge with 'should' comes in when we allow it to influence how we moderate our lives to meet the expectations of others, or to maintain the perception of status quo. And it is particularly problematic when it causes us to choose a life of mediocrity over a life of fulfillment and passion.

While there are times when making decisions solely based on what you should do is totally appropriate, there are also times when it is not, times when living your life means abandoning what you should do and following your heart.

Deciding to follow your heart is not without its challenges

When I started BestLived.com in early 2017 it was a decision that most people thought was completely insane. Sure, they liked the concept, but the idea of leaving a very high paying job in corporate finance to create a start-up company devoted to inspiring people on the road to happier, more fulfilling lives? Many people had a hard time understanding how that made sense.

Fast-forward to today, 7 months later, and it has been one of the best decisions of my life. Sure, running a start-up company, in media no less, is not without challenges. But everyday we grow, and everyday I am reminded of how what we do matters.

A happy life in which you follow your heart is not necessarily a life without challenges, but it can be a wonderful one.

How do you live life on your own terms?

How do you move towards a life inspired by more of what you want to do?

What can you do to begin living a life that makes it possible to follow your heart?

For starters...

Spend more time connecting with who you truly are.

It is almost impossible to know what steps to take in life without understanding who you are and what makes you fulfilled. Consider journaling, making mindfulness a common practice, or making more time for your hobbies or creative outlets.

Whatever you do, make the task of self-reflection and self-discovery a priority.


Spend time understanding what you truly want for your life. A few important questions to ask yourself as you navigate this process are:

When am I my happiest self?

When am I my best, most alive self?

What types of situations make me feel like my strongest and boldest self?

What parts of my life are prohibiting me from being my happiest, best, strongest and boldest self?

Spend time answering these questions. Afterwards, jot down what you would like to see happen in your life over the next two to three years.

What next?

You have thought about what you’d like to see happen in your life over the next few years. Now think about which of those desires are good for you and those you love, and which ones aren’t. There are things that we may want which ultimately would be damaging to ourselves and those we love.

This does not mean that there are not times when what is best for us could result in hurting or disappointing others in our lives. It just means that anything that might damage our own wellbeing, or cause harm to those we love, should be heavily considered and approached with caution.

Time to make a plan

You have spent time reflecting, worked to understand what you want for your life, and looked at how your wants might impact those you care about.

If the end result is that you have decided it is time to let go of expectations around what you should do, and embrace what you want to do, then it is time to make a plan to follow your heart.

As you make your plan, ask yourself the following questions.

How long would it take to achieve what I want?

What financial or material resources do I need to achieve what I want?

What emotional and mental support do I need to achieve what I want?

Answering the above questions can help you identify  any areas in which you are lacking, and figure out ways to compensate for them.

Let go of always doing what you should do

Following your heart despite other people's expectations takes time, mindfulness, and courage. However, doing so can result in a life that is richer and more authentic than you could have ever imagined.