• Damon D'Amore

The Biggest Mistakes People Make When Setting Goals

The three biggest mistakes I see made when setting goals are:

  1. Individuals lack proper motivation to do the work necessary because they think of outcomes in terms of accomplishing their goals instead of the consequences of not accomplishing them.

  2. Lack of defined filters to determine if a goal is in fact a goal and if so is it the right goal they should be pursuing.

  3. The ability to embrace making tradeoffs in pursuit of goals.


1. Proper Motivation

One of the best definitions of a goal that I have read is “The purpose of a goal is to manage future regret.” (Morgan Housel)


Instead of focusing on the gold at the end of your goal-chasing rainbow, think of the consequences and very specific emotions associated with not accomplishing that goal – both for yourself and for whoever may be impacted by the positive outcomes of the goal (recipients of philanthropy, your family, customer experiences, etc.).


In the future when you look back and recount your accomplishments with pride and joy, those feelings will always be less impactful in relation to the regrets you will have for the things you set out to but failed at accomplishing, because you cannot create or buy more time.


You never have time, only intentions.



2. Creating Filters

In order for a goal to be worthy of pursuing and therefore worthy of your time, energy, and whatever tradeoffs you will need to make in pursuit of that goal it should meet three fundamental criteria. Is the goal:

  • Binary – Is there a definite and specific outcome? If you accomplish or fail will it be clear without question?

  • Measurable – Are there ways to measure your progress along the way? Can the goal be broken into smaller steps to both allow for accountability to yourself or a mentor/stakeholder and keep you motivated as you progress through the steps?

  • Actionable – Are you capable of accomplishing or at least beginning the work to accomplish that goal? Do you currently have the necessary resources? And, if not, are you able to acquire those resources?


3. Tradeoffs

Thoreau famously said, “The price of anything is the amount of life that you exchange for it.”


What tradeoffs in time, resources, comfort and short-term rewards are you willing to make in pursuit of accomplishing meaningful goals? Tradeoffs should be specific and include any consequences for your stakeholders by sacrificing current results for the potential of greater future results. Know what you are trading off and what the cost is for doing so.


If you are going to embark on the journey of accomplishing meaningful goals and what matters most, take the time to properly define them and create a personalized plan which will provide you the greatest potential for success.



Damon D’Amore has spent 15 years working directly with C-Suite leaders in Fortune 500 firms. His work at Legacy Mentor focuses on psychological performance and storytelling to gain stakeholder advocacy. Damon speaks internationally on legacy, personal development, resilience, mindset, and applying the lessons of entrepreneurship to corporate environments. He founded multiple companies and is an active board member and advisor to multiple international companies. Half of Damon’s clients are female leaders in the C-Suite.


For information on the next cohort of Damon’s mastermind for female entrepreneurs and female coaches visit www.legacymentormethod.com


Join his newsletter at www.damondamore.com

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