A COO’s Guide to Taking Messy Action as a Recovering Perfectionist

Are you a recovering perfectionist? The terms Messy and COO (Chief Operations Officer) don’t seem to go hand-in-hand. As COO I pride myself in my organization, thoroughness, and technical abilities. They are undoubtedly strengths in my line of work. “Messy” may have had a place in my college art studio, but when it comes to systems and processes, we want streamlined and polished. 

Perfectionism lends itself well to the COO life, but at a cost. Over the years this cost has arrived differently but ultimately it impacts my happiness, well-being, and even my success in all aspects of my life. 

Let’s frame this conversation with a story…

When my daughter was born, a little over 5 years ago, I left my 9-5 job

(which was honestly an 8-7) and jumped into the stay-at-home-mom life. I loved the opportunity to parent her in this way and truly enjoyed this precious time as a new mom.

As she got older, I connected with more and more moms for playdates, birthday parties, and school events. I quickly saw a part of myself step into the picture. 

My perfectionist side. 

It was easy to fall into a state of comparison. As if parenting were a competition and something I needed to be “good” at. I wanted the best for my little girl. So, when I saw other moms throwing amazing parties, packing Bento box lunches, and baking the perfect cupcakes for school bake sales, my perfectionism decided these were things I needed to be doing too. 

At first, my perfectionism pushed me to try harder. I felt I had to be the ultimate “Pinterest mom” to keep up. So I stayed up later than I’d like to admit icing cupcakes (and throwing away/eating any that didn’t look just right), and planned themed parties that left me exhausted. I was doing it all and still, it never felt like it was enough. 

Ultimately, I quickly burnt out. No matter how hard I tried, I felt I wasn’t living up to some crazy expectation I had set for myself. There was always a “better” party or a more delicious treat. The other part of my perfectionism came through, telling me, “don’t even try! You’ll embarrass yourself!” This “why bother” attitude left me feeling like if it couldn’t be just right, I shouldn’t even start. It pulled me away from trying at all. My perfectionism kept me from creating moments that definitely wouldn’t have been perfect, but would have been fun, memorable, and exciting!

I tell this story because the pushes and pulls of perfectionism impact all parts of my life, including my business. As a mother I’ve become more aware of them and where the unattainable standards I set aren’t serving anyone (least of all myself). In my business, I’ve noticed where my perfectionism can be helpful, but where it is also unsustainable, harmful, and limiting. 

In this blog, we’ll explore how to acknowledge perfectionism for the good it does in our lives while also digging deep into the darker side of this mindset. I’ll offer advice from my own experiences on how to resist the tempting pushes and pulls of perfectionism that can keep us from taking action or push us past our limits. 

My Perfectionism Journey

I grew up a complete perfectionist. Let me paint a picture…

  • straight-A student
  • honor roll
  • graduated with high marks 
  • attended the “perfect college”
  • & headed off to my dream job.

I’ve always been a high-achiever. Someone who would set goals and accomplish them no matter what. Sometimes that meant I moved through life with tunnel vision. Sometimes that meant passing on things I might have enjoyed but didn’t attempt because they weren’t going to directly contribute to the goal.

Can you relate?

Over time, I realized that while I checked all of the “boxes” I had created for myself, I also missed out on a lot. Because I had a one-track mind, I didn’t try anything outside the box. I may not have been any good at these things, but could have loved or grown from them if only I’d given them a try. I was so uncomfortable with not being GREAT at something, that often I just skipped it altogether.

This mindset around perfectionism carried into my business and entrepreneurial journey…

All these qualities I cultivated to protect myself, please others, and meet expectations, actually caused me to:

  • wait over 5 years to start my business! I started down the path 6 years ago but scrapped it when things got uncertain. I let the fear of struggling or not doing it perfectly stop me.
  • put off my first hire for probably 6 months because I was afraid of choosing the wrong person for the job (spoiler: I didn’t! ) and someone relying on me to consistently bring in the $ to pay them! (which hasn’t been a problem).
If these experiences resonate with you, you’re in the right place!

I have good news for you… because both of those stories had a happy ending. 

  • I started the business and hired the team. All because I got out of my own way, took imperfect action, and trusted myself and my journey. 

This self-proclaimed “recovering perfectionist” is proof that with the right tools, support, and mindset you can accomplish your goals AND maintain your mental health.

I hope that by sharing my story, acknowledging the positives of perfectionism, and bringing to light the dark side of this personality trait, I can inspire you to take a look at your habits, goals, and actions. Because I want YOU to believe that you can create a business of your dreams and challenge yourself to dream bigger than your perfectionism could ever allow!

The Pretty Side of Perfectionism

Every “fatal flaw” has a plus side. In storybooks and real-life, fatal flaws serve to protect us from someone or something. It’s our armor that helps us feel in control. It carries us through this uncertainty that we call life! So I like to take a moment to appreciate perfectionism (both mine and yours). 

Perfectionism helps me…

  • Produce neat, organized, high-quality work
  • Maintain high standards
  • Cultivate a strong work ethic
  • Notice the details others overlook
  • Stick to deadlines and maintain my commitments
  • Go above and beyond in my client experience

There is a lot of GOOD that comes from this part of me. The key has been to balance this with healthy boundaries so that the darker side of perfectionism doesn’t become harmful to me, my self-worth, and the longevity of my business.

Journal Prompt: What does your perfectionism protect or help you do in your life and business? 

The Pushes of Perfectionism

In the online entrepreneurial world, it can be all too easy to get sucked in by comparison. We are bombarded by Instagram posts, emails, and videos that are meant to celebrate the accomplishments and ambitions of our peers. But if perfectionism has anything to do with it, these forms of media quickly become standards that we feel we must ALSO achieve. 

Our to-do lists grow and grow and our vocabulary is full of “shoulds” and “musts” that leave us drained. Not only is this exhausting, but you might wake up one day and realize that none of the many actions you’ve been taking are aligned with what you want. Instead, you are “doing” on autopilot because you have tricked yourself into thinking that more equals better and that if everyone else seems to be pulling it off, you should be too! 

I’m here to tell you, this is FALSE!

Tip #1 from a recovering perfectionist:

If you feel like you are on autopilot, take some CEO time to pause and reflect. Reconnect with the Vision and Core Values of your business. 

Start with vision-casting so that you can make sure the actions you’re taking are building on what YOU want, not someone else’s version of “success”. When vision-casting, these journaling prompts are helpful:

“To me, success looks like…” or “I know I am being successful when…” 

Then, focus on your Core Values. Once you’ve established 3-5 values that feel empowering and aligned, sit down with your to-do list. Are the things on this list supporting your values? If not, is it possible for you to let them go? How does this feel? Take some time to journal, talk to a business bestie, or reach out to a coach or mentor you trust. This is not a quick fix, but making sure your actions and your priorities are in line will help you manage your time and energy in a way that brings you TRUE success and fulfillment from your work. 

ACTION→ This week, try to take 1 thing off your to-do list that comes from a place of obligation or comparison. 

The Pulls of Perfectionism

Perfectionism in business also comes in the form of imposter syndrome that pulls us away from our goals. If you are a creative entrepreneur, you may have felt this at one point or another. It’s the hesitation to take action because we wonder if we are worthy, good enough, or ready (hint: you always are and always have been).

It may show up as struggling to make a decision or take action, avoiding challenges or failure, and/or dwelling on mistakes. If this sounds familiar, know you are not alone!

Again, our perfectionism works overtime to protect us from the perceived threat of embarrassment, disappointment, or being in over our heads.  But failure and mistakes are what help us grow and evolve. We need to start seeing these challenges as opportunities instead of threats!  

As entrepreneurs, not taking action is the killer of dreams! We chose to blaze a trail, but if we freeze up at every challenging moment, we limit what we can accomplish, create, and achieve in business. As a “recovering perfectionist”, I am constantly doing the work to develop my relationship with failure, learn from it, and welcome it as an opportunity (yes, easier said than done). 

Tip #2 from a recovering perfectionist:

Take imperfect action and get out of your own way. If you identify as a perfectionist this can feel impossible at first (in fact, it can even be paralyzing). We tend to align the quality of what we produce with our personal value. While it is healthy to have pride in your work, there must be a balance. It’s important to honor this part of you while challenging yourself to bust through the perfection tendencies that are holding you back. You can practice taking imperfect action by starting small and with people you trust. 

Action → Start small. This could look like the following:

  • Send over an email within 3 minutes of writing it (ditch overthinking, tweaking, and obsessing)

  • Jump on a Clubhouse or Instagram live with a trusted business bestie. Doing hard things is easier with people you respect and trust. The live aspect stops you from re-recording until it’s juuuust right!

  • Publish the first draft of that freebie or blog post you’ve been thinking about for months. Show up and serve your audience! Remember, you can go back and refine it after you get it out into the world if you still feel you need to. But the scariest part…putting it out there, is over! 

  • Braindump a social media post on a topic you care deeply about. Set a timer for 10 minutes. At the end of 10 minutes, post it. No going back and re-wording again and again. And if you find a typo after you posted…it’s not the end of the world, that’s what the “edit” button is for!

3 Reasons to Ditch Perfection as an Entrepreneur

With the opportunity to reflect on the pushes and pulls of perfectionism in your business and some ideas to inspire you into aligned, messy action, let’s dive deeper into your WHY. 

Without a true understanding of what’s on the other side of our limiting perfectionism, it can be hard to commit to moving past our habits and out of our comfort zone. Here are the 3 reasons why I regularly practice ditching perfectionism as an entrepreneur!

#1 To grow you have to get uncomfortable

It’s not fun to be uncomfortable. It’s easier to stay somewhere predictable and familiar where we can feel in control. But I’ve come to realize this limits us in so many ways as creative entrepreneurs. I’ve made a concerted effort to get uncomfortable, get into the messy, and take the chances…

…and you know what?! It’s better living at the end of your comfort zone. I’ve learned to lean into the uncomfortable feeling. I’ve learned to take the chance. But it’s still SO hard. And is something I have to work on constantly (hello mindset work!).

# 2 There is clarity in action

I’ve been trying to embrace messy action because (while I love planning) I’m a firm believer in the fact that clarity is found through action.

Over the last two years, I’ve discovered this to be true for myself.  I cannot predict the clarity I will stumble upon in my personal and business growth until I put myself out there. Honestly, some of my best offers and ideas have come without planning and when I least expect it! Many of these pleasantly unexpected offers went over way better than the offers I planned to the nth degree and flopped! 

I am and always will be a planner at heart. However,  I’ve come to understand there is ALWAYS the possibility of analysis paralysis. I still like to have a plan A, B, C, D, E, F… (I’m not trying to change WHO I am, but how I respond). But, while staying true to my nature, I have also learned to be definitive, make a decision, and play it out without a guaranteed outcome. Knowing that nothing is set in stone and it can always be changed is hard but healthy. I am slowly but surely learning that the backup plans aren’t so bad. 

COO tip: for super anxious people like me, here is my best advice for taking messy action (the kind where success isn’t guaranteed). Think of the worst-case scenario. Let’s be honest, that probably won’t happen, but dream up how it could all go wrong. Decide how you would handle it if it did. If you can develop a plan for that…it might help settle your anxiety and get you to take action.

# 3 You never know unless you try.

If we stay in our comfort zone, we know the result: status quo. But I know you didn’t take the leap and start a business for things to just stay the same. So now’s the time to ask yourself: do you want to be left wondering… “what if?”

In the words of Wayne Gretzsky, “You miss 100% of the shots you don’t take.” If perfection is pulling you away from taking action, you already know the outcome. But if you decide to just get started, allow yourself to be messy, and welcome mistakes, you open up so many amazing possibilities!

We’re in this together!

Growing this business and stepping out into this world of entrepreneurship has not been easy. It’s been hard. It has hit on some of my deepest insecurities, been one of my biggest challenges, and I’ve had to compromise and sacrifice sometimes to make it work.

I’ve cringed when things weren’t perfect but I could count them as done. There’s a reason I’m still a RECOVERING perfectionist. I’ve learned, in this world, sometimes DONE is better than perfect. If we wait for the perfect time, the perfect opportunity, the perfect fit, the perfect offer…we’ll be waiting forever. 

Nothing is perfect. And that’s what makes it beautiful and interesting a lot of the time. But it took me a long time to be ok with “not perfect” and it is something I will continue to work on every day.

And I’ve come to appreciate it.

So, if you are someone who has perfectionist tendencies, please know I totally get it, you are not alone, and we probably need a support group for recovering perfectionists (just kidding, but seriously my inbox is always open)!

I know so many high-achievers, who exist in this space, who struggle with this too. And I think it’s important to talk about, acknowledge, and keep cheering each other on as we take one imperfect step after another. 

If you identify as a recovering perfectionist, I encourage you to share your story in the comments below. We can combat perfectionism every single time we see and hear that others aren’t perfect either. These reminders help us stay grounded, realistic, and connected on this entrepreneurial journey!

I’ll leave you with two questions:

  1. What’s one thing you can take off your to-do list (AKA stop keeping up with the Joneses)?
  2. What’s one thing you can do IMPERFECTLY today? 

Cheering you on!

Help someone else who is a recovering perfectionist! Pin this to Pinterest:

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