From Loopholes to Launchpads: Transforming Entrepreneurial Excuses into Stepping Stones

Excuses are like *ssholes…..

This week’s blog is all about The Loopholes of Entrepreneurial Sabotage. Have you ever heard that saying, “Excuses are like *ssholes, everyone has them and they all stink.” Whether you still have yet to email your accountant for t*x season or you’re reading this email because you don’t want to email that client back - I totally get it…..

Last week on the blog, we talked about how some businesses and products were created because of loopholes - maybe your own business is a loophole kind of business. Now, it’s time to ask yourself if you’ve waited until the last minute to do your t*xes…and if you have, why? And if you haven’t, why not? 





The answer can be best summed up in….OMG, YOU GUESSED IT - A LOOPHOLE! 


F*ck these d*mn loops, I know it’s a whole thing I’m obsessed with and didn’t really realize how obsessed until we got to this 4th email on loops. Stay with me though, it’s a good one.   


This week is all about how loopholes impact our mindset, and luckily Gretchen Rubin, a NY Times Best Selling Author on Happiness and thought-provoking observations, of these so INSERT LOOPHOLE FOR ME - I didn’t have to do a lot of work on this one. She created 10 Loopholes that most of us have and most of us use that stop us from creating new habits. 

Read more below about how you might use each of these as an excuse!

10 Categories of Loopholes by Gretchen Rubin

1. False choice loophole - “I can’t do this, because I’m so busy doing that”

2. Moral licensing loophole - “I’ve been so good, it’s okay for me to do this”

3. Tomorrow loophole - “It’s okay to skip today, because I’m going to do this tomorrow”

4. Lack of control loophole - “I can’t help myself”

5. Planning to fail loophole - "I put myself in this place for other reasons, but now that I'm here, how can I resist?"

6. “This doesn’t count” loophole - “I’m on vacation”

7. Questionable assumption loophole - "It's impossible to quit sugar."

8. Concern for others loophole - “I can’t do this because it might make other people uncomfortable”

9. Fake self-actualization loophole - “You only live once! Embrace the moment!”

10. One-coin loophole - “What difference does it make if I do this just this one time?”


Did you read any of these and just go: YUUUUUUPPPPPPP

Here’s where I become a late-night infomercial host, “But wait! There’s more….” You would TOTALLY buy something from me right?

I’ve taken the liberty of evolving these loopholes into excuses you might use when applying it to your small business. So, let’s look at them from an entrepreneur’s perspective.



10 Categories of Loopholes - The Entrepreneur’s Excuses

1. False choice loophole - “I can’t go to that networking event, because I’m so busy finalizing my newsletter for tomorrow.”

2. Moral licensing loophole -  “We’ve crushed our sales this month, that means we can just relax these next few weeks and ride the wave.”

3. Tomorrow loophole - “It’s okay to skip updating my QuickBooks today, because I have to reconcile the end of the month’s books tomorrow anyway.”

4. Lack of control loophole - “Why bother with a social media strategy, the algorithm is always changing.”

5. Planning to fail loophole - "This month’s sales are going to be terrible since everyone’s on vacation, I might as well just take some time off too and work on all this later."

6. “This doesn’t count” loophole - “It’s the first time we’re offering this (product/service) so it doesn’t matter if we overspend a little on marketing - we’ll be on track on the next go round”

7. Questionable assumption loophole - "It's impossible for us to compete with the franchises and big corporations, they have ALL the answers already."

8. Concern for others loophole - “We can’t get rid of (product/service offering that isn’t doing well and you know you need stop offering it), a few of our clients really love it.” Or his another good one, “(insert employee name) will catch on eventually, there’s no reason to fire them yet…” 

9. Fake self-actualization loophole - “You only live once, I’m the owner and I say let’s just do it!”

10. One-coin loophole - “What difference does it make if we just take the entire team to lunch, it will be fine for our budget!”

So, I ask again…did you read any of these and just go: YUUUUUUPPPPPPP


First, remind yourself you’re not a bad person for doing any of these things. You are just a human doing a really f*cking hard thing called “Entrepreneurship.” 


FYI in these next “10 Lists,” you are just going to pick the ones that resonate most.and you’ll skip the rest.



Take a Reality Inventory:

Look at the list above and see which of those really stands out to you, you probably already know, and then look at the list below and match it with your Entrepreneurial Saboteur. Don’t worry, you’ll get a “fun” name. 

1. The Dichotomy Dude - This saboteur simplifies complex decisions into false dichotomies, convincing you that you must choose between critical tasks instead of finding a way to balance multiple priorities.


2. The Past Prodigy - This saboteur reminds you of your past successes to justify complacency or risky decisions in the present, discouraging consistent effort or caution.


3. The Procrastination Princess - Always suggesting that there's more time tomorrow, this saboteur encourages delaying important tasks for the allure of immediate ease or pleasure, undermining urgency and discipline.


4. The Trend Chaser - Thriving on the fear of missing out, this saboteur pushes you to jump on every new trend, often leading to scattered focus and resources, and a lack of strategic direction.


5. The Opportunist Oracle - This saboteur rationalizes poor preparation or lack of effort with the promise of unexpected opportunities, encouraging a reliance on luck over planning.


6. The Fiscal Freewheeler - Promoting a lax attitude towards budget and resources, this saboteur uses transitional periods as an excuse to bend the rules, risking financial health for short-term gains.


7. The Defeatist Diplomat - By assuming insurmountable odds against larger competitors, this saboteur advocates for inaction, discouraging innovation or effort in areas like sustainability or niche market exploration.


8. The Comfort Keeper - Preferring the status quo to potential disruption, this saboteur argues against changes that could benefit the business in the long term, prioritizing immediate team comfort over growth.


9. The Risk Romantic -  Cloaking impulsiveness in the guise of boldness and living for the moment, this saboteur tempts you to take uncalculated risks, bypassing due diligence for the thrill of the gamble.


10. The Pennywise Pretender - Minimizing the significance of small expenses or deviations from the plan, this saboteur undermines financial discipline by suggesting that minor missteps won't impact the overall success.


Each of these entrepreneurial saboteurs represents the internal voices that rationalize taking shortcuts, avoiding difficult decisions, or indulging in immediate gratification. Identifying and challenging these saboteurs can help you maintain focus, discipline, and a strategic approach to your business decisions… or at least they will make you aware of your go-to method for sabotaging yourself and your business. 

Here’s the thing, this is a behavior you’ve probably done and justified for a long time, so it will keep happening for a while, but at least you're now present to it. For me it’s about turning that saboteur into a sage with a quick little flip of loophole to possibility. 

So, your last lil’ list of 10 goes something like this…turn your saboteur into a sage of action.

1. If you fall into the False Choice Loophole and have been dubbed “The Dichomoty Dude” your new possibility is Opportunity Cost Recognition.

Opportunity Cost Recognition Action: Evaluate the opportunity cost of choices to prioritize actions that offer the greatest benefit to your business. This can help allocate time and resources.


2. If you fall into the Moral Licensing Loophole and have been dubbed “The Past Prodigy” your new possibility is Reward-Based Motivation.

Reward-Based Motivation Action: Set milestones and reward yourself upon completion. This helps motivate continuous improvement and goes all the way back to the loophole of continued, buildable progress. 


3. If you fall into the Tomorrow Loophole and have been dubbed “The Procrastination Princess” Your new possibility is Strategic Delaying.

Strategic Delaying Action: Deliberately postpone decisions because the idea can be developed further, so you can make better-informed decisions, make sure to really nail down the “why” of delay. 


4. If you fall into the Lack of Control Loophole and have been dubbed “The Trend Chaser” your new possibility is Delegating and Outsourcing.

Delegating and Outsourcing Action: If possible, delegate tasks to team members who are more skilled than you or can do the tasks faster and more efficiently (yes, I can read what I just wrote and I know it’s still totally not easy.) Outsourcing certain tasks can help you focus on doing the thing you really need to do.  


5. If you fall into the Planning to Fail Loophole and have been dubbed “The Opportunistic Oracle” your new possibility is Opportunistic Flexibility.

Opportunistic Flexibility Action: Another hard one, but take advantage of the unforeseen opportunities. Remember businesses started because of loopholes. You always have the option to pivot or punt when needed. 


6. If you fall into the “This doesn’t count” Loophole and have been dubbed “The Fiscal Freewheeler” your new possibility is Creative Breaks.

Creative Breaks Action: Take a 10-minute break when needed and maybe try scheduling them during the day when you need them most. These little breaks can lead to innovative ideas. 


7. If you fall into the Questionable Assumption Loophole and have been dubbed “The Defeatist Diplomat” your new possibility is Challenging the Status Quo.

Challenging the Status Quo Action: Let’s question the 'impossible. You are an entrepreneur, which means you can do just about anything! Question industry assumptions and even your own assumptions and ask yourself what’s been overlooked.


8. If you fall into the Concern for Others Loophole and have been dubbed “The Comfort Keeper” your new possibility is Empathetic Leadership.

Empathetic Leadership Action: How is what you’re holding on to impacting your business because you don’t want to “ruffle feathers.” But more importantly, ask yourself how is the concern for others holding you and your business back from its full potential.


9. If you fall into the Fake Self-Actualization Loophole and have been dubbed “The Risk Romantic” your new possibility is Experiential Marketing.

Experiential Marketing Action: Embracing the moment can inspire seriously great marketing campaigns. Create memorable experiences that resonate with your customers on an emotional level, strengthening brand loyalty. 

10. If you fall into the One-Coin Loophole and have been dubbed “The Pennywise Pretender” your new possibility is Incremental Improvement.

Incremental Improvement Action: Remind yourself small, consistent improvements and enhancements are key. Whether it’s slowly improving your operating systems, your products and services, or your staff training these can lead to big evolutions in your business and ultimately competitive advantages over time. 

So, whether you’re nodding your head with a knowing grin at each loophole-turned-excuse or found yourself confronting the saboteur you didn’t even know was leading the entrepreneurial rollercoaster this whole time, the key takeaway with all this loophole discussion is…AWARENESS. 

You know it, I know it, being an entrepreneur is thrilling, challenging, and sometimes makes you want to throw up - just like the loops on the rollercoaster ride. It’s so tempting to get off, be done, quit, and never get in line again… that’s exactly what your newly named saboteur shows up and loves to do…spoil the fun. 


Now, it’s time for your sage to come through. It’s time to take action against your saboteur and turn that loophole into a launch pad for growth. Sadly, I know you’re totally bummed at this fourth and final email all about loops, but remember this sh*t is hard and you’re not alone. Every one of us faces challenges, doubt, temptation, and fear, but what sets each one of us apart is our ability to push through and use the loopholes to create future possibilities. Just like last week when I talked about Airbnb and my virtual assistant, Jenn. 


Cheers to your next challenge in entrepreneurship, from loopholes of sabotage to sages of possibility. May the next email be free of loops, and instead, direct lines of information, because 4 emails of loops makes us all… a lil’ loopy. Stay courageous on the entrepreneurial ride, because you’re capable and have the strength to turn loopholes into possibilities! 

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