How To Break The Cycle Of Giving Up On Your Goals

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I'm Jen -  A web designer and strategist who has made it my mission to equip and inspire entrepreneurs to build a brand and business that allows them to live life on their terms.

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You would probably agree that the feeling of letting someone down is not a pleasant one. It’s the dreaded anticipation of wondering what they think about you, and why or how you could have disappointed them. So many situations in life lead us to striving to meet the expectations of other people. Yet we often fail to meet our own expectations, and unfortunately, it seems as if we do so pretty easily. We let time pass by, along with our goals and we shrug off the failures without any immediate consequence for doing so. 

I bring this up, because to me, goal setting is about so much more than jotting down a quick intention on a piece of paper. It’s about making a promise to yourself. The goals we set for ourselves come from somewhere deep within. They have meaning and purpose, and yet they can be so easy to ignore. As someone who loves to plan for the future, I know how discouraging it can be to struggle with goal setting and more than that, failure. It feels as if we live in a society that encourages big dreams, but then fails to make room for achieving them in a realistic way.

Over the years, I’ve really considered this problem as I’ve reflected on what I did or didn’t accomplish and why. And I’ve pieced together a few tricks that allow me to plan for the future, while also making room for the good stuff to happen in between. In fact, when it comes to conversations around goal setting, I think that’s a great place to start. How can we set realistic goals that set the standard for growth and improvement, while still making room for the joyfully unexpected aspects of life.


While it might feel painful at first, the first step is often looking at the past with an objective point of view. You didn’t get here by chance. Just like accomplishing a new goal takes time, so does consistently failing to meet one. It’s within the day to day actions we take that promises are held or broken. Over time, when you fail to keep promises to yourself, you trust yourself less, and inherently give yourself less responsibility and therefore less expectation. Your outward behaviors become viewed as internal character traits. You see yourself as a person who quits, fails, or struggles to do hard things. And so the die is cast, so to speak.

As you settle into this pattern, eventually you find yourself in a place where you’re stuck. You’ve created a habit of letting yourself down, and set a precedent that it doesn’t matter.  The only way to get “unstuck” is by taking it one step, and one day at a time. But first, you need a little reality check to get out of that place. Let’s be honest, goals on paper are bright, shiny and filled with rainbow colored promises. But actually taking the steps to achieve those goals? Well that’s filled with early mornings, afternoon challenges, and a long, difficult journey that you’ve convinced yourself in the past you’re unable to make.

Now it’s time to reframe that past, acknowledge the failures that belong there and move on with simple, actionable steps forward. If you want to change your life, one small promise at a time you have to acknowledge that it is you and only you that has held yourself back up until this point and then decide that you’re going to do things differently from here forward. You can do so by reframing those past failures into something positive.

  • Acknowledge the behavior, not the trait. Failing to meet a promise is not who you are, it’s something you did.
  • Shut down the excuses you’ve used before. For example, if you told yourself you didn’t have enough time, examine how you spent that time instead and analyze if it was worth not accomplishing your goal.
  • Use your past as inspiration to do things differently, not an indicator of future habits.


You make the choices you do in life for a reason. And failing to meet a promise or take action on a goal is a choice. You’ve acknowledged the past and what it means, but it’s also time to let go of it in order to make room for a different future. Instead of analyzing every action, you need to have a thorough understanding of what motivates you to take them. This part of the process is so important, because it allows you to develop the consistency you need to move forward. 

I love and often rely on a few personality tests that help me gain a better understanding of myself before I sit down to any goal planning session. (If you’re not familiar with personality tests, a few of my favorites are Enneagram, Clifton Strenths Finder or 16 Personalities.)

Based on my personality results I have a habit of focusing on creativity and visionary thinking – making my decisions on emotional aspects of things that I enjoy, rather than realistic ones that consider the demands of daily life. On the other hand, I also know that because of this, I thrive under routine and it allows me to make room for the flexibility and freedom I always crave. 

Basically in the past, I made decisions based on feelings, and those feelings often lead to failure. If I didn’t feel like working out that morning, I wouldn’t. If I didn’t feel like writing a blog post that day, I didn’t. I’ve learned that I can’t use my feelings as a source of support. Instead, I need to commit to routine and productive habits that allow me to connect to the “real world” so to speak, on a daily basis. 

  • What problems have you faced in the past that got in the way of your goals?
  • What are strengths that you can focus on to reach your goals, rather than weaknesses?
  • What needs to change in order to stick to commitments in the future?


With the internal work done, it’s time to start taking practical steps to actually achieving your goals. This is where keeping promises to yourself becomes challenging, because it means acknowledging the truth that there is no magical formula from where you are to where you want to be. Instead, it’s committing to one small promise at a time, that compounds on one another.

You’ve done the deep work, now it’s time to do the hard work and just start. The trick is in starting small. If your goal is to start a blog, then start by writing a blog post. Sounds obvious, right? Unfortunately, the first place we think we need to start is often halfway through the process and is what causes us to become overwhelmed and to quit before we achieve any real momentum. If you tried to build a new website and blog without any experience, then became overwhelmed by the technical aspects, and never even made it to the part of actually writing blog posts – you’re further behind than if you had just started writing and publishing on a pre-built platform.

You can take the time to research, plan and improve after you’ve gotten started. The focus in the beginning is to simply take action. Action creates momentum, which creates small wins, which creates consistency. Just be realistic about what you can actually accomplish. 

  • Start with small promises that are easy to keep, like reading a business book for 10 minutes every night before bed.
  • Set goals that you’re naturally interested in and that serve you well. If you set a goal that doesn’t align with your life, it’s going to feel forced trying to keep it and you’ll end up back in a routine of failure.
  • Reward yourself with more responsibility. As you build back trust in your successes, start to take on larger commitments that you know you can keep.

Keeping promises in life may feel difficult when you have a pattern of failure, but they become more attainable when you realize they’re actually just built on small, everyday choices. Goals don’t have to start big. They can be whatever size you need based on your season of life. The most important thing is that it aligns with your intentions, that it provides you with a quick win to keep moving forward, and that you have the opportunity to create routine in order to make it happen. Consistently choose what feels right for you, and that will support your ability to keep moving forward and growing in your goals, one day at a time.

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Hey, I'm Jen

I'm so happy you're here - let's collaborate on something good.

My husband calls me Jennifer, but everyone else calls me Jen.
I started my first online business and blog way back in 2015, when I just knew I wanted to do life differently. I've always had a notebook full of scribbles and really big dreams. While my business has shifted a bit along the way, my love of this online industry has stayed the same.

And I have the skillset of being able to build a strategic website to thank for that. I truly believe that with anything is possible with a domain name, and a little web design magic.

Meet Jen


Inspirational content for the dreamers and the risk takers. Inspired by the simple things in life.