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Surviving Self-Doubt & Imposter Syndrome in the Entrepreneurial Wilderness: A Sarcastic Guide for Women


Surviving Self-Doubt & Imposter Syndrome in the Entrepreneurial Wilderness: A Sarcastic Guide for Women

Welcome to the jungle, ladies – where the wild world of entrepreneurship awaits, armed with its fair share of challenges, pitfalls, and the occasional man-eating beast. Strap in, because we're about to take you on a sarcastic yet authentic journey through the treacherous terrain of entrepreneurship, especially for the women who love a good challenge – or at least that's what we tell ourselves to keep from keep from crying into our morning coffee.


The Elephant in the Room: Self-Doubt and Impostor Syndrome


Let's start with the elephant in the room: self-doubt and impostor syndrome. Ah yes, those delightful little demons that whisper sweet nothings into our ears and make us question our every single move. Because nothing says "entrepreneurial success" like the crippling voice of self-doubt, am I right?


These two formidable foes, which often intertwine, aren't just buzzwords; they're real challenges many of us face. Impostor syndrome convinces us that despite our achievements, we're frauds undeserving of our success and accolades, while self-doubt amplifies our insecurities, casting a pall over our abilities, decisions, and worthiness. Together, they create the perfect storm of anxiety that can paralyze even the most accomplished among us.


Did you know self-doubt and impostor syndrome isn't picky about who it visits? Yep, it's got a free pass to everyone! But guess who's leading the charge on this not-so-fun rollercoaster? You guessed it – us ladies! A whopping 60% of women hold off on their entrepreneurial dreams because of this sneaky phenomenon. For lack of a better word, we're our own worst critics.


From Tiny Daredevils to Doubtful Adults


As adults, we're sometimes plagued by these two unwelcome guests that can take up permanent residence in our minds leaving us feeling broken and deflated. But rewind to our childhood days, where these insecurities were about as common as a unicorn sighting and confidence flowed as freely as the juice boxes during recess. Remember some of those carefree moments when we were little?


We danced like nobody was watching, played dress-up with our mother’s heels and lipstick; we spun around until the world spun with us, and belted out tunes with gusto, pretending we were the stars of our own MTV music video.


For any Gen Z readers wondering "WTF is MTV?"—imagine YouTube, but on an old-school TV network that only played music videos and reality shows where people fought over trivial things like who ate the last slice of pizza. But whether you knew MTV or not, the point remains: we were fearless little risk-takers, gleefully stomping in puddles and tasting snowflakes without a second thought, while chasing after our dreams with reckless abandon.


Now here we are, trading in our daisy crowns and crazy dance moves for spreadsheets and boardroom meetings, Googling "how to adult" while simultaneously contemplating quitting and becoming a professional Netflix binge-watcher!


But let's get real for a moment. You might be wondering, "What does the boundless confidence of children have to do with my current struggles of self-doubt and imposter syndrome?" The truth is the contrast between the fearlessness we once embodied and the inadequacy some of us now feel is striking. As children, we were unabashedly ourselves, oblivious to the fears of failure or the judgment of others. Life was a grand adventure, and we approached it with a sense of curiosity and wonder, unafraid to dive into new experiences with wide-eyed excitement.


Kids, despite lacking the understanding of calculated risks, possess an innate adaptability that allows them to navigate new experiences with enthusiasm and resilience—a trait that is especially valuable in the unpredictable landscape of entrepreneurship.

Upon entering adulthood, some of us find that our once unshakable confidence can waver, like a tightrope walker feeling a sudden breeze—momentarily unsettling, yet a reminder of the delicate balance we strive to maintain.


It’s that never-ending narrative where we feel we must morph into a boss babe juggernaut, flawlessly balancing a booming career with a family straight out of a Hallmark movie, settling down with a dream partner so ripped they could rival Greek statues, all while being the proud owner of a 12-bedroom mansion that could outshine those seen on an episode of Selling Sunset. Because clearly, nothing screams "living your best life" like channeling Bridget Jones, chugging down a bottle of Chardonnay, flaunting a “perfect” Instagram façade and then secretly ugly crying into your pillow at night. It's like starring in your very own rom-com, except instead of Hugh Grant showing up at your doorstep, it's just another Amazon delivery of impulse-bought self-help books and a notification from your plant-watering app, shaming you for neglecting your leafy companions again.


How Society Convinced Women We Should Be CEOs, Supermoms, and Social Media Stars All at Once



How Society Convinced Women We Should Be CEOs, Supermoms, and Social Media Stars All at Once

Okay, so the above portrayal might’ve been somewhat exaggerated (just a tad), but it does underscore a significant truth: self-doubt and imposter syndrome are pervasive issues that largely stem from the crushing weight of societal pressures bearing down on us like a bad hangover after a night of questionable decisions. Coupled with the pressure to excel in every facet of life, this creates unrealistic expectations that can lead to feelings of inadequacy and fear of failure. The perpetual quest for “perfection” often masks the underlying issue—that success does not equate to self-worth and attempting to "have it all" is like trying to fit a square peg into a round hole – it’s exhausting and ultimately futile. Nor is it mentally, physically, or spiritually healthy to pursue such ideals.


So, you know what Ladies, let's just blame society for setting the bar impossibly high and convincing us that life should be a flawless highlight reel, when in reality it’s more like a blooper reel with occasional flashes of brilliance.


For now, let’s recalibrate those unnecessary expectations by laughing in the face of the "have it all" chaos, because honestly, who needs that kind of pressure? If you’re someone who is grappling with self-doubt and imposterism, then keep reading to discover some helpful techniques you can apply to self-manage those feelings.


Dare to Crawl, Walk, and Run: Techniques to Becoming a Confident Powerhouse


As an old proverb wisely says, you must learn to crawl before you can walk, and walk before you can run. The journey to conquering self-doubt and impostor syndrome is just like that – it's not a quick fix, nor is it a one-size-fits-all adventure. It's a gradual process that demands patience, time, and a generous dose of self-compassion. You'll need a mix of creativity, resilience, and unconventional strategies that resonate with your unique strengths and aspirations. So ladies, let’s take this journey together, one step at a time, and help you transform into the confident powerhouse you were always meant to be!

 

But before we dive into the self-managing methods and techniques, let’s circle back to that brave little spirit within you, just waiting to break free. Now just to be candid, this isn’t about recapturing your youth but adopting the childlike archetype that this article has touched on. Think of it as reclaiming your inner mischief-maker whose imagination ran wild and free and believed anything was possible. That resilience, that "nothing can stop me" attitude, is exactly what we need to summon. So, grab your metaphorical band-aids, slap on your superhero cape, and get ready to rumble your way through the entrepreneurial wilderness with the same enthusiasm you had when you were ruling the playground.

 

1.    Embrace Curiosity: Turn Doubts into a Learning Expedition


Approach challenges with the curiosity of a child exploring the world. Instead of viewing obstacles as insurmountable, see them as opportunities for growth. Ask questions, seek advice from mentors or peers, and remain open to new ideas and perspectives. Instead of keeping a traditional journal, start a "Curiosity Log." Document every question, idea, or interest that pops into your mind, no matter how weird it may seem. Some of the craziest and simplest ideas led to multi-million-dollar ventures, such as the sleeved blanket and the sticky notes.

 

Create a ritual where you explore one curiosity each week, whether it’s learning a new skill, attending a workshop, or speaking to someone who inspires you. This approach transforms self-doubt into a quest for knowledge and personal growth, while turning uncertainties into opportunities for exploration.

           

2.    Be Authentically You: Craft Your Brand Story


Remember the unfiltered authenticity of childhood? Embrace that same spirit in your entrepreneurial journey by developing your "Personal Brand Storyboard." Just as a child fearlessly expresses their uniqueness, use visual elements such as mood boards, sketches, and mind maps to illustrate your journey, values, and aspirations. Instead of trying to fit into a mold or imitate others, celebrate your quirks, strengths, and personality traits instead of conforming to societal expectations. Authenticity is magnetic. Read that again – AUTHENTICITY IS MAGNETIC! It builds trust with your audience, clients, and collaborators. Whether you're an introvert, extrovert, or somewhere in between, your genuine self is your greatest asset in navigating the entrepreneurial wilderness.

 

3.    Practice Self-Compassion: Hug Your Inner Kiddo


This is a BIG one. Kids are often forgiving of their mistakes and shortcomings, whether they understand it or not; it's all part of the learning process. Stefanie Stahl, clinical psychologist and bestselling author of The Child in You: The Breakthrough Method for Bringing Out Your Authentic Self, highlights that developing self-compassion is crucial for healing. She says, “self-worth is the epicenter of our psyche while our self-esteem is expressed in our beliefs.” In other words, “It’s not facts that make up our sense of reality, but rather our interpretations of those facts." This quote from Stefanie Stahl perfectly encapsulates the importance of how we perceive ourselves.


When negative self-talk throws you for a loop, this is the time for you to be extra kind to yourself. Just as kids need positive reinforcement, adults need it too. Be mindful of the inner dialogue you have with yourself. Treat yourself with compassion and understanding, reminding yourself that setbacks are a natural part of life. Therefore, acknowledge your accomplishments, celebrate your progress (no matter how big or small), and remember to express gratitude for your efforts as often as possible. And for those moments when imposter syndrome rears its ugly head, Cheri Beranek, CEO of Clearfield, has a nifty trick up her sleeve - The BRA Technique. Yes, you read that right. And no, it’s not the surgical method for perking up saggy boobs, but it’s equally supportive. It stands for Breathe, Relax, Allow – like giving your mind a little lift. Here’s how you can apply it:


1. Breathe: Take a deep inhale, hold it for a sec (don’t turn blue!), and then exhale like you’re blowing out the candles on a super-sized birthday cake. It’s amazing what a little oxygen can do for the old noggin.

 

2. Relax: Unclench your jaw, drop your shoulders from where they were practically grazing your earlobes, and release that tension like you’re tossing a heavy bag of worries off a cliff.

 

3. Allow: Give yourself permission to be imperfect to have those moments of doubt without letting them define you. Every stumble is a step towards growth so cut yourself some slack and recognize that perfection is a myth. Instead, focus on progress and self-compassion. As the wise Mark Twain once said, “Continuous improvement is better than delayed perfection.”


The BRA technique isn’t just a fun handy acronym; it’s a reminder to be present, to tune into reality even when it feels like you’re wading through quicksand. It’s a practical, effective way to manage those moments when imposter syndrome tries to gate-crash your entrepreneurial party. For more on Cheri Beranek's BRA Technique, check out the original article on Entrepreneur.


4.    Build Your Dream Team: Cut the Toxicity and Find Your Cheerleaders


Just as kids rely on their support system for encouragement and guidance, it's crucial to surround yourself with a positive, uplifting crew. First things first, cut the toxicity from your life. Anyone that doesn't serve you psychologically might mean you’ll need to distance yourself or cut 'em loose altogether. Yes, it’s harsh and painful, but sadly, life can be a cruel reality filled with the fakes and snakes of the world who feed on the misery and downfall of others. That’s why it’s important to examine your circle; who has your back and who doesn’t.


Toxic friends or even family can chip away at your self-esteem. If being around someone consistently makes you feel drained, anxious, or bad about yourself, then chances are they’re probably toxic. But be sure to make an assessment before making any drastic decisions to protect your well-being. On the flip side, there are tons of great and amazing human beings out there, so don’t hold back from meeting those gems!



Build Your Dream Team: Cut the Toxicity and Find Your Cheerleaders

 Now for the fun stuff: building your dream team! Just like kids naturally form playgroups, you need your squad of mentors, peers, and fellow entrepreneurs. Don’t hesitate to reach out for support. Join networking groups, attend workshops or seminars, and dive into online forums. Picture it as recess time – you’re not just there to play but also to learn, grow, and find your tribe. Surround yourself with a supportive network that offers valuable insights, encouragement, and reassurance during challenging times. Schedule regular check-ins with your support system to discuss your progress. Share your experiences and seek advice on overcoming professional obstacles. Think of these interactions as your entrepreneurial playdates – they’re essential for keeping your spirits high and your motivation soaring.

 

5.    Get Your Ducks in Line: Embrace Structure Without the Overwhelm


Just like how kids thrive with routines and structure, entrepreneurs can benefit from clear goal setting and strategic planning. Setting goals using the KISS framework (Keep It Simple and Sweet) can prevent overwhelm. Instead of bogging yourself down with detailed milestones, set monthly or quarterly goals that are straightforward and manageable. Here’s how to apply it:

 

Set OKRs (Objectives and Key Results): a roadmap for personal and entrepreneurial success. For example, aim to boost physical fitness to compete in a marathon: run 4 times a week. For professional OKRs, dive into this article: Harnessing the OKR Blueprint for Success.

 

Top Three Priorities: Every day, identify the top three tasks that are high priority. This keeps you from getting lost in an endless to-do list and ensures you’re making steady progress.

 

Regular Check-ins: Schedule regular check-ins to assess your progress. Adjust your goals as necessary to stay on track without feeling overwhelmed.

 

Why It Works:


  • Reduces Overwhelm: By breaking down your big dreams into manageable tasks, you’re less likely to feel suffocated. This approach helps in tackling self-doubt by providing a clear path forward.

  • Boosts Confidence: Achieving small, regular milestones can boost your confidence, reducing feelings of imposter syndrome.

  • Maintains Focus: A structured plan helps you stay focused on your goals, minimizing distractions and self-doubt.


Tools That Help:


  • Project Management Apps: Tools such as Trello, Asana, or Notion can help you organize your tasks and track your progress.

  • Time-Blocking Techniques: Allocate specific times for focused work to ensure you’re consistently moving towards your goals.


6.    Nourish Your Inner Kiddo: Balance the Hustle with “Me Time” 


Maintaining peak performance as adults demands more than just a greasy cheesy burger and an IV drip of Red Bull to power up. It requires a holistic approach to health and well-being. Just like kids need their nutritious meals to grow big, strong, and healthy, we adults need our own version of TLC. A healthy body equals a happy mind, and though it’s a cliché, it holds true.


Your mind is the HQ of creativity and problem-solving, deserving your utmost care. It isn't a physical object you can see, touch, or measure in the same way you can with your body, but it's where your dreams and thoughts take shape. Neglecting it is like forgetting to water your plants—they might survive for a while, but they won't flourish.

 

So, how do you keep your mental garden blooming amidst the hustle and grind? For starters, it's about enjoying life's simple pleasures—the kind that soothes your soul and makes your inner child do a happy dance.

 

Look for the Bare Necessities…


“The simple bare necessities, forget about your worries and your strife…” Can you guess which


Disney classic these lyrics are from?


That’s right, The Jungle Book! As cheesy as the song is it has a point. Embracing the bare necessities isn’t just about survival; it’s about thriving in the jungle of modern life. Just like Mowgli needed Baloo's laid-back wisdom, we all need our own version of downtime and simple pleasures to keep our sanity intact.


Whether it’s hitting the gym for some endorphin-fueled fun, savoring fresh juices (sorry, cocktails!), hydrating with plenty of water, getting our beauty sleep, and eating well, taking care of your body is like duuuh! Experts have been drumming these simple facts into our heads for decades and there’s plenty of information online than you can shake a banana at to guide you, so no excuses. Don’t “Bridget Jones-it” by diving into that delicious tub of Ben & Jerry’s or waiting until January 1st to slap a nicotine patch on to your forehead.


Limiting alcohol? Yeah, that’s right up there with trying to tame Shere Khan with a feather duster. Sure, those spur-of-the-moment pleasures might feel like a wild escape, especially when you're drunk swinging from the chandeliers. But let’s face it, the aftermath of knocking back one too many isn’t exactly a party favor – think more balance, less buzz.


Savor the Little Things


In challenging times, it's crucial to appreciate the small joys in life. Whether it’s the tantalizing smell of freshly baked banana bread wafting through your kitchen or the warm embrace of the sun on your skin during a stroll—these moments matter.


Incorporate moments of relaxation and joy into your entrepreneurial journey, much like the playtime kids enjoy. Have an early night. Sleep in if you don’t need to be up early! Take regular breaks to recharge your batteries and prevent burnout. Engage in activities you love outside of work, whether it's taking a spicy salsa class, indulging in a good book, or spending time with friends and family. Pay attention to the things that genuinely bring you happiness and make a conscious effort to incorporate them into your life to stay positive and grounded.


Try a Digital Detox


Step away from screens, phones, work platforms, emails, and prioritize self-care. Nothing beats a good ol’ pamper sesh! Get a mani-pedi, book a heavenly Thai massage, sink into a nice relaxing bubble bath or get a blowout – whatever floats your boat. Just be sure to switch your mind off in those moments and enjoy the present. A refreshed mind is better equipped to tackle challenges and overcome self-doubt. Remember to schedule regular “playdates” in your diary because (as the L’Oréal motto declares) you’re worth it!


Conquer self-doubt and impostor syndrome


And there you have it, Queens! A mildly sarcastic, empowering guide to conquering the beasts of self-doubt and impostor syndrome, straight from the entrepreneurial jungle playbook.


Embrace curiosity like a kid on a quest for adventure, stay authentically you in a world of copycats, and shower yourself with the compassion of a forgiving child. Seek support like you're forming your own Avengers team, and don't forget to add a splash of structure to your schedule.


Taking breaks and having fun is not just a suggestion—it's a mandatory lesson in the school of life. As you adopt these habits, you'll not only learn to transmute those intrinsic feelings of uncertainty into sources of strengths, but also fearlessly execute your business endeavors.


Spoiler alert: our next HerStorytime blog will delve into the thrilling topic of execution! Stay tuned for more adventures, laughs, and lessons.

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