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Your Worst Enemy is You: Overcoming the 7 Signs of Self-Sabotage

Everything is hopeless…


Everyone around you is trying to get you…


Life is spinning out of control.


Does any of that sound like you?


If it does, know that you’re not alone.


As an entrepreneur, you’re up against a variety of challenges. Challenges that come from your business interactions and activities, but also challenges might not be entirely external.


We all have that little narrator in our heads - you know the one - spewing out commentary on our every move. In many cases, this commentary isn’t all that positive or helpful.


This little voice is the main driver of self-sabotaging behavior.


And believe me, I know it all too well.


Self-sabotage is a massive roadblock when it comes to achieving success, regardless of the industry you operate in. But more than that, self-destructive behavior can impact how to approach business relationships…


What is Self-Sabotage?


Self-sabotage is where you create internal conflict (knowingly or unknowingly) that undermines your own goals.


Now, this is a simplified definition because there’s a lot of different ones that mean the same thing. I like how social worker and Senior VP of Operations and Behavioral Health, Kelly M. Pennington, Ph.D explains it:


“[Self-sabotage is] the act of getting in your own way, i.e., creating barriers to achieving an intended or expected outcome.”

That’s the perfect explanation because that’s exactly what’s happening - it’s the internal obstacles WE create that keep us from building - or even starting - down the path toward entrepreneurial success.


So why do we do it?


According to psychologist Nick Wignall, there are two groups of self-sabotaging behaviors – conscious and unconscious.


  • Conscious self-sabotage is when we knowingly do things that are antithetical to our goals. For example, knowing we have a project to do but actively choosing to watch the latest season of a TV show, play video games, or scroll through social media instead.

  • Unconscious self-sabotage happens when we do things we aren’t even aware that we’re doing. This is where that little voice comes in – for example, you want a closer connection with a person, be it romantic or platonic, but instead you do the opposite and pull away as soon as the first minor issue arises.


Now, to be clear, everyone encounters self-sabotage from time to time, but some people may experience this phenomenon on an ongoing basis. As author Maureen Brady writes:


“Sometimes we self-sabotage just when things seem to be going smoothly. Perhaps this is a way to express our fear about whether it is okay for us to have a better life.”

That leads me to the 7 signs that you’re *SECRETLY* self-sabotaging.


Sign #1 – Focusing on what’s not working


When it comes to business, especially as a real estate investor, you’re going to have wins and losses. That’s just how life works – but, the difference is you focus on the losses and only the losses.


And because you’re so focused on what’s going wrong, you end up getting stuck in that mindset. You expect the worst to happen and when it doesn’t, you still end up looking at the downside.



This flavor of strong self-sabotage behavior can be particularly challenging to cure because it carries with it a whole mindset that you have to work to undo. Which, needless to say, can be difficult.


In this case, the first step you should take is to start documenting BOTH the wins and the losses…


Write them down!


Tell a friend!


Re-enforce your positive mindset by actively feeding it those positive stimuli.


Sign #2 – Comparing your success to others


Comparisons - the thief of all lasting joy.


A long, hard look in the mirror might reveal that you AREN’T as successful as someone you aspire to be like; your sibling, your coworker, or even a competitor. This is of course envy or jealousy, an unfortunate motive that most of us carry inside ourselves.


We see the successes of others and we envy their results. Ultimately, we may even begin to ignore the crowning achievements we’ve already won for ourselves.


This is where the concept of collaboration over competition comes into play; it’s the idea that you find more success by working with others instead of competing with each other.


Sign #3 – Fear is fear itself


Now, fear can be good.


Making changes in your life can be scary, but they can also be massive opportunities.


However if fear of the unknown - like the future - causes you to panic, then you’re likely letting fear control you. Fear can paralyze you and stop you from doing things because you’re afraid of what will happen.


For example, applying or asking for a promotion at work or even starting your own business cripples you because you don’t know what the future will hold. Worse, you envision a bleak future where the very idea of a new opportunity smells like failure to you.


Truth is, change (and even a little ambiguity) is good for you.


The best way to keep fear of the unknown at bay is to concentrate on the present.


This goes back to the first sign: make sure you focus on the wins you have! Your wins are based on you, no one else! So let loose and celebrate when you lose some weight or see your credit score increase.


Sign #4 – Feeling like an imposter


Do you ever feel like you might be an imposter?


Like everything that’s happening to you, especially anything positive, should be happening to someone else?


I’ll raise my hand to that one. Even now, despite all the successes I have in my life, sometimes I feel like I don’t deserve the success.


Imposter syndrome is a real condition, a condition where you believe that you aren’t deserving of the success you have or that you’re unqualified to receive such acclaim.


This is classic self-sabotage behavior where you doubt your own abilities, feeling as though you’re a fraud and worse, that others will realize it, too.


Just like the other self-sabotage behaviors I’ve mentioned, this is one that’s tough to really overcome. Like I said, I still have bouts of this, but again you have to focus on the present and the achievements you’ve made.


Sign #5 – Disorganization


On a normal day, our lives are chaotic.


We have kids, we have jobs, we have a bunch of TV shows we need to catch up on…


With so many things happening at once, it’s easy to get lost in the shuffle. Most of the time, this is just a normal result of a hectic week and we reset.


But being disorganized robs us of our focus – the focus to have set goals and to go after them. This is about more than just a messy desk; this is about having and chasing multiple things without having finished the first.


I call it ‘shiny object syndrome’.


The way to defeat this sabotage tactic is to hold yourself accountable to what you truly want to do. If you want to launch a new aspect of your business by the end of the year, for example, you have to set the goals and pathway to achieve that.


And then hold yourself accountable if you miss major milestones, like setting up important meetings or making calls. Do whatever you need to – set up alarms, add it to your calendar, put it in a planner, etc.


Anyone in the AstroFlipping community will know, we have accountability partners to ensure that we’re on top of tasks and are doing what we need to do.


Sign #6 – Procrastination


Procrastination goes hand and hand with disorganization because, let’s face it, sometimes we don’t want to do hard things.



You know you have to make phone calls or you have to set up appointments, but instead you start watching the latest binge-worthy show on Netflix. You put off that task until it’s down to the wire and now, you’re rushing through it in order to meet a deadline.


Like disorganization, procrastination happens from time to time and we’re all guilty of it; the difference is how we conduct the rest of our time. But putting off the things that are hard leads to us chasing things that are easy and fun.


Which leads to us becoming disorganized and going after every new, shiny object that we can.


There’s nothing wrong with taking time off – in fact, you should! – but the time off should be a recharge so that you can come back and focus MORE.


Sign #7 – Avoiding relationships


In business, as in life, relationships are everything.


As a real estate investor and a wholesaler, my relationships are a key component of my success. Making connections – with contractors, other investors, other wholesalers, real estate agents, etc – helps me build up relationships that will further my business success.


But when we're self-sabotaging, we either cut off our relationships or we start self-isolating. The reason being is that we believe we’re going to be hurt. I’ve certainly had business dealings that didn’t work out the way I wanted.


Society tends to focus more on the romantic side of this, which also counts, but there are many different types of relationships, from family to friends to business. As with being afraid of the unknown, withdrawing from relationships because of past hurts only deprives us of opportunities we can have in the present.


Going out and meeting new people means getting out of our comfort zone, but doing so offers so much value in return.


One Day at a Time


Self-sabotage keeps us small and stops us from achieving our potential.


But as Nick Wignall stated earlier, unconscious self-sabotage isn’t as easily seen as the conscious type. So how in the world are you supposed to stop this?


Well, it means you might have to do some homework.


I know, I know, you didn’t come to read this blog and leave with homework. But it’ll be good, I promise.



Your homework is to sit down and explore some of those conscious and unconscious self-sabotaging behaviors you might have. And it’s probably not going to take an hour or even a day, so when you start to feel something coming on, take note of it.


It will be challenging because there’s a lot of emotion involved with self-sabotage because you’re in the middle of it and you’re just thinking about what’s happening right in that moment.


But that’s where you have to take a step back and look at the actions you’re doing. How you go about this is up to you – maybe for you, it’s talking to someone you trust and having conversations about it; maybe it’s writing your observations down.


For me, I look back on the previous week and reflect. I make sure to highlight the successes and if there was a loss, instead of ruminating on it, I look at how I could handle things better and take it as a learning experience.


And that’s what you should remember from this – take these as lessons to improve and learn.


Lastly – you’ve got this.


I believe in you and I’m sure there are tons of others who do as well.


So go out there and be the awesome person you already are!


As always, if you need support or guidance, you’re welcomed at AstroFlipping.


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