7 Ways We Self-Sabotage

How To Turn It Into Self-Mastery

Want to know what separates the great achievers in the world from the mediocre?

Winners and losers have the same goals. Why is it that only some win while most fail and stay down?

What separates them is simply…


The winners choose to play a different game from most. The winners choose a different mountain to master.

Most people think the problem in front of them is actually the problem they need to solve and master. The greats understand that the problem in front of them is just the symptom, and the true mountain to conquer and master is themselves.

There is nothing holding you back in your life more than yourself.

In the end, it is not the mountain that you must master, but yourself.

Brianna Wiest

So the name of the game here: how do you overcome all the ways you get in your own way?

We call this self-sabotage. In this letter, I’m going to break down:

  1. Why we self-sabotage

  2. How to overcome self-sabotage

  3. Ways we self-sabotage

When you understand how to choose the right game to play, it won’t matter what challenges or problems you face in the world… you’ll be playing a winning game from the inside out.

In the end, the mountain that is you, is the most fulfilling one to conquer.

Why We Self-Sabotage?

As Brianna Wiest explains in “The Mountain Is You”, self-sabotage is when you have two conflicting desires.

One is conscious, the other is unconscious.

On one end, you have a conscious desire to accomplish something, to move forward in your life in some way. This can be building a business, writing a book, getting into a relationship, or going after something you want.

On the other end, is an unconscious desire to fulfill a need.

It’s often a need you didn’t realize you have or did realize but neglected. Could be a need for safety and security. Or a need to feel acceptance, belonging, and love. As a way to cope with this need not consistently being met, you unconsciously create a behavior to feed it.

Self-sabotage is when that unconscious pattern gets in the way of your conscious desire to go get what you want in life.

A self-sabotaging pattern I struggled with was my resistance to publishing my writings.

On one end, my conscious desire is to write and share more value with the world, and one day publish a book or two. On the conflicting end, I had an unconscious need for safety, creating a fear of failing and being seen in my vulnerability.

The mountain that I had to overcome was not my writing but my conflicting desires.

It was way more fulfilling to conquer my self-sabotage than it was to see the vanity metrics that came with my published writing. While the metrics and compliments helped validate my writing, the real win was knowing I can overcome the ways I got in my own way.

Choosing the right game matters.

After helping over a dozen entrepreneurs scale their businesses beyond 7-figures, I can echo their sentiment that their greatest sense of accomplishment wasn’t their business but it was overcoming their fears and self-sabotaging patterns.

Choosing self-mastery and facing the mountain that is you is the only path to freedom.

How To Overcome Self-Sabotage?

Step 1: Build Awareness

The first step of the process is to understand deeply your self-sabotaging pattern and your needs.

  • What is it that you truly want in your life? (conscious desire)

  • How are you getting in your own way? (unconscious behavior)

  • What are your needs that you might not be aware of? (unconscious need)

Pull out your journal and reflect deeply on these questions: be honest, be real.

Write down specifically all the things you’re not happy with in your life. Every problem or challenge you’re struggling with.

The first step in healing is always to take radical responsibility, to no longer be in denial of the honest truth of yourself.

Step 2: Manage Your Emotions

The second step is managing your emotions and finding ways to process your emotions safely.

  • What feelings and emotions are coming up around your self-sabotaging pattern?

  • How can you validate and safely process these feelings?

  • What are these feelings trying to tell you?

The thing about self-sabotage is that you often don’t need to be told what to do.

You already know what you need to do and what you want to do. What’s holding you back is your fear of feeling the difficult feelings that come with self-sabotage.

You self-sabotage because you’re more committed to not feeling than you are committed to changing.

Validate your feelings. Make space to safely process your feelings by feeling them all the way through to completion.

Then listen to what your feelings are trying to tell you. Emotions carry wisdom. Your anger, sadness, feeling of unworthiness are trying to tell you something.

Slow down to the speed of wisdom and you’ll hear the needs that your feelings are pointing to.

Step 3: Meet Your Needs

The third step once you’re clear on your needs is to find healthier and more productive ways to meet your needs.

  • What are ways can you feed your needs productively and effectively?

  • What support from others can you resource to fulfill your needs?

Understand your needs. Meet the ones you’re responsible for. Then allow others to help meet the ones you can’t do on your own.

The less you fulfill your needs in a healthy and productive way, the louder your unconscious pattern (self-sabotage) will be, to feed that need.

Step 4: Take Forward Action

The final step is to keep taking action in the direction you want to go.

Knowing why you self-sabotage is one thing, overcoming it and taking action even when it’s uncomfortable is another.

You don’t hold yourself back in life because you’re not capable of moving forward. You hold yourself back because you don’t feel like moving forward.

  • How can you separate your feelings from your actions?

  • What systems can you create to keep you productively moving forward?

  • What support and accountability can you build in?

When you understand that self-sabotage is not actually a bad thing, but simply an inner cry for change. You’ll stop struggling with the symptoms and start tackling the one true issue in your life…

The misalignment of your values, desires, and needs.

Let’s break down some of the ways we self-sabotage and how to overcome them.

7 Ways We Self-Sabotage

Here are some of the ways we self-sabotage and examples of conflicting desires and needs.

1) Procrastination

This looks like not doing or avoiding the thing you need to do.

I’m talking about the fear-based resistance to doing, not the being lazy kind of resistance.

Unconscious Need: Safety or Certainty

Unconscious Pattern: Resisting or avoiding action to stay with what’s comfortable. Or resisting action because what you’re working on is not aligned with what you truly want.

What to do:

  • Get clear on what you really want and why you want it

  • Know what your vision, values and goals are (need help, check out my Strategic Vision Planner)

  • Make sure what you’re working on is fully aligned with what you truly want

  • Make your desires bigger than your fears

2) Playing Small

What this looks like in life and business, is staying with what’s comfortable instead of surpassing your limits and potential.

It’s being content when deep down you desire a much bigger and more expansive life or way of being.

Unconscious Need: Safety or Worthiness

Unconscious Pattern: Playing small and being content with your smallness because it’s safe and familiar (for you and people around you)

What to do:

  • Know what you want and know you’re worthy and deserving of it

  • Create micro-wins outside your comfort zone

  • Celebrate your wins and progress

  • Shift your baseline of worthiness to your new standard each time you win

  • Be ok with people no longer resonating with the new you

3) Chasing Shiny Objects & The Next Thing

This is when you’re jumping from one thing to the next without finishing or completing the last.

Always chasing a new chapter or the next thing and never fully showing up or establishing yourself in the last one.

This doesn’t just show up at work, it can also show up in relationships.

Unconscious Need: Safety

Unconscious Pattern: Chasing the next thing to avoid staying with or confronting the discomfort of the current thing

What to do:

  • Pause before running to the next thing

  • Confront the discomfort

  • Know what you truly want and if the current thing is aligned with it, lean in deeper

  • Explore your attachment styles and what it would look like to establish a secure attachment with the current thing

4) Perfectionism

This is wanting things to be perfect before you fully show up.

Or thinking you must get things right the first time, or every time.

It’s a self-imposed, and usually unrealistic, expectation that keeps you from simply doing the thing.

Unconscious Need: Approval and Acceptance

Unconscious Pattern: Needing to get everything right or having everything be right to avoid the possibility of failing or being wrong and not being accepted and loved.

What to do:

  • Focus on progress, not perfection

  • Measure yourself against your gains (from where you started), not your gap (where you want to be)

  • Celebrate lessons learned from your trials and error

  • Done is better than perfect

  • Focus first on doing the right things, then later optimize for doing things right

5) Over-complicating or overthinking

This is when you’re making things more complicated than it needs to be.

Spending more time and energy than needed thinking about something instead of actually doing it.

Overcomplicating and overthinking are the biggest enemies holding back most entrepreneurs.

Unconscious Need: Approval or Certainty

Unconscious Pattern: Over-complicating or overthinking things to get it right so you can avoid the possibility of failure or the discomfort of doing the actual thing

What to do:

  • Get really clear on what you want

  • Ask better questions to create clarity:

    • How can I make this simple? (use the 80/20 rule)

    • How can I make this easier or effortless?

    • How can I make this more fun or enjoyable?

    • What does done look like? (done over perfect)

    • What’s the first clear step?

  • Have a bias toward action, start with the first step

6) Staying with what you don’t really want

This can look like doing something you don’t really want to do and justifying it because it’s what others want.

It could be staying with a course of action, a project, or a relationship that isn’t aligned and justifying it to please others.

It could even be staying with something (or someone) because you invested so much into it already. It was once aligned and something you wanted but is no longer.

It’s an attachment that’s forcing you to want something you don’t truly want.

Unconscious Need: Approval and Acceptance

Unconscious Pattern: Staying with something or someone you’re not aligned with and justifying it to avoid disappointing others (or your younger self)

What to do:

  • Again, know what you truly want (your vision, values, goals)

  • Be ok with letting go of what isn’t aligned, even if it disappoints others

  • Know that disappointing your Future Self will hurt more than disappointing others

  • Create your own criteria for success instead of measuring yourself against other’s ideals

  • Explore your attachment patterns and create secure attachments in your life

7) Avoiding or suppressing feelings

There are 2 tendencies that keep you from building the emotional intelligence to get what you want in your life:

  1. You suppress your own emotions or avoid feeling them to stay comfortable

  2. You make other people’s emotions your emergency so you don’t have to deal with your own

Building emotional intelligence is a key stepping stone to overcoming all other self-sabotaging patterns.

Unconscious Need: Safety

Unconscious Pattern: Avoiding feelings and processing emotions to avoid the discomfort and vulnerability of the process

What to do:

  • Acknowledge and validate your feelings

  • Find methods and safe spaces to process your feelings

  • Learn to draw wisdom and lessons from your feelings

  • Separate your feelings from your desire to take forward action

Putting This In Action

You now understand what self-sabotage really is, why we do it, and how to overcome it.

You’ve gotten examples of ways you may be self-sabotaging and the possible needs and patterns.

Now let’s put it all into action using my 3-step formula for self-mastery:

Step 1: Define

  • Get clear on what you truly want: vision, values, goals (use this Strategic Vision Planner)

  • Write out all the ways you’re self-sabotaging

  • Follow the process in the “How To Overcome Self-Sabotage” section of this letter

Step 2: Decide

  • Pick one pattern you’re committed to work on

  • Don’t try to tackle them all at once

  • Decide, commit, and share your commitment with others for accountability

Step 3: Design

  • Design a game plan

  • Schedule in time to do the inner work (feeling your feelings and feeding your needs)

  • Schedule in time to do the outer work (taking forward action even if it’s uncomfortable)

  • Build in support and accountability

  • Schedule in time to reflect, realign, and plan forward

  • Practice self-compassion and mental fortitude

  • Keep it going until becomes your new way of being

  • Then pick a new pattern to work on and keep repeating the process of self-mastery

That’s it for this letter. Thanks for reading!

I know this letter is deeper on the inner work side and may bring up emotional triggers and resistance. If you need support with any of this work, please reach out to me.

Let’s keep growing and winning together!

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P.S. Whenever you’re ready, there are 3 ways I can help you:

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  2. I offer 1:1 coaching to help entrepreneurs systematize their business, overcome self-sabotage and buy back time so they enjoy more of their life

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