On being messy (Behind the scenes of the mindset challenges of entrepreneurship)
Sometimes when I write a post or an email for you all it's because I've got a very clear perspective on a problem that I’m seeing pop up for my clients (or generally other high achieving women with people pleasing and perfectionist tendencies) and a very practical set of recommendations on what they should do about it or an explanation of what’s going on the scenes with clear takeaways.
This is not one of those posts.
One of the most interesting shifts that has happened in my life since I've become a coach is this endless pressure to feel like I have all the answers.
In corporate America, even when you were increasingly senior (when I left, I was a Senior Director), you still had people above you giving you feedback and advising from their experience. It was entirely permissible to still be seen as having room to grow, or still being learning.
But now that I run my own business, and a coaching/education business at that, I’ve felt enormous pressure to project an image of being an expert. You’re offering solutions for people that they’ll spend their hard earned money on so there’s this pressure to make it clear why you know what you’re talking about, establishing authority and expertise in whatever area of focus you have.
This is exceptionally true in coaching. But I think it gets blown way out of proportion.
Especially because this pressure to be perceived by others as an expert begins to translate to holding yourself to the standard of always feeling like an expert. And if you don’t, it’s really hard not to feel like a fraud, like “why should they trust me when I don’t have xyz figured out?”
But here’s the thing: I don’t think any of my clients expected me to be perfect when they hired me. I know this because I’ve spoken to them about it and even more so, because when I hired my first coach, I don’t believe that she was absolutely perfect, evolved, never had any doubts or insecurities. In fact, some of the most powerful moments of coaching were moments of realizing “oh she’s just like me” which gave me permission to see that I could overcome certain thought patterns or behaviors just like she had.
Realizing that she was a work-in-progress didn’t make me trust her less, it made me trust her MORE because she felt more relatable and made my goals feel more achievable.
Holy hell, do I wish I had the clarity of that sentence 6 months ago. Because, my friend, I’m here in this post to talk about why I think we all need to be a little messier and that starts with me.
Because the last 9 months have been a JOURNEY for me. And as all journeys, they’ve had stages.
October - December: Doubt and Confusion
January - March: Pretending things are fine
April - July: Avoid Avoid Avoid
I’ve been thinking a lot over the past few weeks about my business, my lifestyle, what I want for myself long term. And I will admit that there were a solid weeks at least where I was considering shutting this business down and starting from scratch. I’m not at that place anymore, in fact, I’m quite optimistic about what’s to come for me, but I realized I’d be doing y’all a disservice if I wasn’t open about what’s been going on in my head as I’ve navigated the last 9 months and the biggest learning I’m working through personally because I know that you probably need to hear it as much as I did.
I hope me sharing this openly helps you accept yourself a little more, makes you feel a little less alone and makes your goals feel more achievable too.
Behind the scenes on a the mindset challenges of an entrepreneur, confidence coach and 30 year old woman (and how I’m working through them)
The pressure to get it right
If you’re anything like me, you’ve spent the majority of your life trying to get it right. This is obviously where so much people pleasing, high achieving, codependency, perfectionism and so on and so forth kicks in but more practically then that, if you feel like you’ve spent your life looking at a massive life-sized to do list and focused on year after year moving your way through them, then we have a lot in common.
For me, taking the leap of faith to start my own business and become a coach was a major diversion from the checklist I had been moving my way through and it felt like a profound signal - “I am no longer doing things to make other people happy. I am chasing my own fulfillment and satisfaction now.”
I wish it was that easy.
Because you don’t override a lifetime of caring what other people think and people pleasing with one form to the secretary of state filing an LLC. And it has been harder than I expected month after month, day after day, to tune out the opinions of clients, followers and peers about what I should be doing, what I should sell, what I should post, how hard I should work, and so on.
We are all familiar with that deep, almost existential feeling of “this isn’t quite right.” In fact, we should all be deeply grateful for it because it’s connected to our deepest intuition of what is right for us.
The problem with the “isn’t quite right” feeling is that it doesn’t give you the instruction manual to find what is.
Which means that when you’re approaching the end of your first year in business and feeling “this isn’t quite right” - you don’t get an instruction manual on whether it’s your process, the topic you’re coaching on, the structure of programs you’re offering, the business model or something entirely different and unknown.
So in the fall of last year, I started in earnest trying to figure out what it was.
I considered pivoting niches entirely and focusing on one of my other passions - negotiation or personal finance. I considered shutting down private coaching entirely and only offering group programs. I considered launching an entirely separate business focused on my love of travel or my experience with social media.
In all of these considerations, I was, as I always have been, searching for the right answer. One that made sense. I needed it to make sense to my audience, to the logic of how to run a business, to the long term vision I have for my life.
But I can now look back (and let’s be clear, this story is far from over) and realize that I felt so lost in trying to figure out a way to make it all make sense because I was playing an unwinnable game.
You see, the key piece about trying to figure out how it would “make sense” is to ask “make sense to who?”
To my clients? I understood that some of the people who hired me for dating coaching back in the day might not make this transition with me.
To my audience? Similarly, I logically understood that it’s normal to lose followers who only resonated with an older version of the business and this can be for the best to find your real true ideal clients.
To my friends and family? I had already moved through much of these fears (although they never fully go away) regarding my personal circle’s opinions of my business.
To me? Dun dun dun… there it was. The most obvious and difficult option. There was no outside opinion that could give me security that I was making the right call. I was going to have to figure out a way forward that felt right to me and the bar for it “making sense” was whether this next step in my business and my life (because in solopreneur world, they’re hard to separate) was authentic and sustainable to me and for me.
What kind of business would really be authentic to who I am? And for that reason make it something I could sustainably do for the long term?
These two things are so important because you hear over and over again when it comes to entrepreneurship, advise like:
Know your why, this is what will keep you going when things get hard
Don’t build a business pretending to be something you’re not because you won’t be able to maintain it
Focus on something you could talk about forever, otherwise you’ll get bored.
These pieces of advice further spiraled me into the doubt and confusion era. Why? Because…
We are not archetypes.
I am an eldest daughter (and niece and grandaughter, on both sides of my family). Responsible, a little (okay a lot) opinionated and always trying to be “the grownup” one.
I’m an enneagram 3 wing 2 and ESFJ. (Which if you consider the above makes eminent amounts of sense).
I’m a human design generator (which never really made sense to me before but I’m learning more to love my inner knowing and the importance of following my joy).
I’m a Sagittarius Sun, Libra Moon, Cancer Rising. For yeaaaaaaars, I rejected my Sagittarius self, believing I should have been born a Capricorn and everything would have made sense. I’m organized, highly motivated, a mature communicator but always caring a ton about the people around me (hi Libra!) and definitely more emotional and sensitive than a lot of people around me (hey Cancer!). I didn’t like being called impulsive or spacey… (little did I know I’d spend a lot of time embracing my traveler, sage Sagittarian side!)
Between Blair and Serena, I’m mostly Blair (other than the blonde) and a Charlotte with a dose of Samantha (uhhh… cause I have to be).
In my advertising days, I was a strategist and new biz (which told you a lot about me vs. being in creative or accounts).
In college, I was a Pi Phi - very distinct from the Thetas or Kappas.
But here’s the thing about all of these - they’re not who I am.
We love these categorization systems, these archetypes and in many ways, nobody loves them more than women like me who want a clear set of characteristics to embody that give us the keys to the life we want. If we fit neatly into an archetype then we can understand our strengths and get a roadmap to how to resolve our weaknesses. What works about us makes sense and the things that are holding us back make sense.
By fitting ourselves into an archetype, we make sense.
And as you know, I’ve been on a journey to try to make myself make sense so these systems were especially tempting this year.
But at a certain point, they become a cage.
Because when you identify as an archetype, there are things you do and things you don’t do. So what happens when you’re feeling an inexplicable pull toward an action or a behavior that doesn’t naturally slide into your identity?
Internal conflict. That’s what happens. Speaking from experience.
Because here’s the thing that has become very obvious over the past 9 months, the full expression of who I am (and who you are) never fits into an archetype.
If you feel like something about you is wrong or doesn’t make sense because it doesn’t cohere with who you feel you’re supposed to be, it might be the archetype that’s the problem and not the thing about you.
Humans are supposed to be dimensional. Full of contradictions. Complicated and ever evolving. We’re supposed to be messy. If for no other reason than the fact that we are emotional beings that don’t always act in complete coherence with maybe what we should do or what makes sense.
As long as we have our limbic, “lizard” brain playing a very large part of running the show, we’d be very well served to let ourselves a bit off the hook and allow for mistakes, incongruencies, contradictions, evolution and growth.
Throughout the last 9 months, but especially in January - March, I was putting on a front. For you all, for my personal life, and to some degree to my clients (but they might have gotten some of the most honest takes).
I believed that I needed to hide the messy parts of me that didn’t make sense, at least until I could make sense of them myself. I was scared that if I shared the things I hadn’t figured out yet or the parts of me that were still very much work-in-progress, you wouldn’t see me as an expert anymore. My clients wouldn’t want to learn from me anymore.
Let’s be blunt, I didn’t think you’d get it - I was worried I’d confuse you or scare you away.
In reality, I was confused myself and rather than have to show up not knowing the answer, I figured it was easier to pretend I had it.
Bitter pill to swallow when I realized this. But this is partially the journey of a coach, to constantly, over and over again, own up to the ways you aren’t living the advice you’re giving to your clients and learn how to hold yourself more accountable.
Because more than anything else in my life, I’ve felt my life was always a journey of unexpected combinations.
My parents, who divorced when I was 2 years old, were a story of opposites. I always joke: my mom likes wine, my dad likes beer; my mom loves theater, my dad loves sports; my mom is a planner, my dad is spontaneous; my dad is wise for her years, my dad is a kid at heart; my mom is sometimes a little to serious for her own good (you know it’s true, mom!) and my dad is maybe a little too playful for his own good.
And in my life, I’ve always straddled worlds - first and foremost, bouncing back and forth between their houses as a kid. In high school, I worked on plays and musicals and managed the basketball team. In my advertising days, the compliments I got most were “you understand the operations but also have an eye for new business.” After a few years of growth and one major promotion, my boss explained that in order for me to keep growing with the company, I needed to pick a track, I explained to him: “my biggest value is in both.” I’ve long been a translator between teams, worlds, perspectives.
When I decided to start a coaching business, I deliberated often - dating or personal finance/negotiation? I was passionate about both topics, had developed some armchair expert level expertise in both and felt like both were urgent and important for my ideal customer. But I couldn’t do both, right? Right. That wouldn’t make sense.
So I picked one. I could talk about dating and confidence for a long time, right? (Narrator voice: maybe not as long as she thought.)
It was the better part of a year before I came to terms with the fact that I couldn’t only talk about dating and confidence for ever. Why?
Because those topics were deeply interrelated with other topics and keeping things in clean little boxes just didn’t resonate with me anymore. Confidence was related to self-trust, which was related to habit-building, which was related to productivity, which was related to working style and career decisions and so on and so forth.
Because I was particularly passionate about another topic at the time and not talking about it felt like cutting off part of me in terms of my sharing. Social media is a funny thing and we all talk about being authentic and sharing both the key parts of your business and also letting your customer get to know you but then every. post. must. connect. to. the. business. Yeah, that’s harder than it sounds.
Because by not having these unexpected combinations, I was hiding that complicated, not-for-everyone part of me that is what makes me me.
And to put it lightly, I was struggling. Which leads me to…
Highlight reel vs. behind the scenes
Literally every single person on this planet has heard the quote: “Don’t compare your behind-the-scenes to everybody else’s highlight reel.” Or Reels, now that we live in the social media era. But you can hear the phrase out loud and still feel deeply deeply like a mess because you seeing people living their European Girl Summer or the engagement post or the promotion announcement. And somehow it feels almost impossible to believe that they aren’t as happy as they look.
We all logically know that not to be true and yet it’s really friggin’ hard in those moments.
As we entered into late spring and early summer, I truly felt like my life had started to fall apart. I’m sure I’ll probably share more specifics at some point about the events that were occurring in that time, but some are still ongoing and quite sensitive, so I’m going to stay rather vague for now - I trust you understand why it’s important I do some processing privately first.
But this is the part of my work that has been the hardest to figure out - I know sharing the feelings I was navigating, the thought patterns I was working to change and the topics I was tackling, processing and trying to move through were probably EXACTLY the thing that would be most helpful and healing for you all to hear.
You could probably have related to me on an even deeper level and felt more seen and understood.
And yet, if I were to share this stuff in its rawest sense, I’d have to be messy. I’d have to show up in my imperfections for all of you to see (this is when a follower count on social media starts to get scarier and scarier).
The more I’ve thought about all this, I realized that I was carrying all my pain, all my questions, all my “it doesn’t make sense” and I was undervaluing you all. Every single client I’ve worked with in Private Coaching and in my group programs has:
had a desire for growth and learning
has known how to handle nuance and see that things take time and nothing is perfect immediately
has been drawn to real humans to learn from, work with and relate to (real humans a.k.a. imperfect humans)
I had (or really until I hit publish on this post, have) a choice of whether I want to be able to be authentic with you all, deeply connect on the human level or present a polished, expert/authority level persona and have to hold back the parts of me that are the most real, work-in-progress, and messy.
I’ve made one choice for the last 9 months. And it hasn’t been working. My business has suffered, my happiness has suffered, my creativity has suffered, I’ve suffered for it. Because I was trying to live a highlight reel for my social media and in order to do that, I made the behind-the-scenes even harder.
So even though I’m a little scared and I’m not sure it’ll work, I’ve decided to make a different choice.
I’ve decided to be messy.
The most important reason, the biggest motivator for me to get over my own bullshit and make a different choice, honestly is…
Greater connection (including giving others permission to be authentic)
I want to create deeper connections with you (whether you’re a current, past or future client or a follower who will never purchase but just really enjoys the content - I’m happy to have you here too!) and with myself.
I know by being brave and willing to be myself more openly and more publicly, I’ll continue to live more of what I teach my clients - embracing imperfections, being a work-in-progress, owning what’s right for you over what’s popular, if for no other reason than I hope you’ll hold me accountable.
I also want more of those moments that I have in session with my clients and like I’ve had with my coaches over the years (including over the past 9 months as I’ve worked with some amazing women) - I want more:
“oh my god, I feel the same way.”
“Me too! It’s so nice to hear someone else going through the same thing, nobody talks about it.”
“I can’t believe you’ve been thinking that too. That makes me feel so much better.”
“I’m obsessed with it too. You need to try ____ next.”
“When you tried ____, how did it work? We have similar _____, so I trust your perspective.”
I also, more than anything else in the world, want you to feel more permission to be authentically yourself, authentically messy, authentically not making sense. And I want you to feel it sooner than I did.
Because I don’t yet feel it yet, but I feel in my soul that this is the best way for me to get there - by being brave and starting to show myself more work-in-progress. And I think it’s especially important to share this part because my hunch is that in order for you to truly embrace your own authenticity, it will require a similar leap of faith.
Which brings us to:
My promises to myself (and you) moving forward
1.I commit to sharing thoughts and insights when they feel important, even if they’re not perfect yet.
This means, it might be in the form of an Instagram story or a vent session on TikTok, because sometimes my thoughts aren’t fully formed enough to warrant a full post yet. I’ve spent too much time having a thought and going “ehhhh, I should wait until I’ve got my head wrapped more around it.” No more of that.
Practically, this means you’ll probably hear more “I’ve been thinking a lot about…” and “I’m trying to figure out…” I’ve decided that the types of clients I want to work with don’t need me to have it all figured out because they know that they also need to figure things out on their own. They want to hear not just what I’m figuring out, but the thought process of how I work through these things. They actually would benefit enormously from the draft version of a thought and seeing how it transforms.
2. I commit to sharing the things that authentically interest me, across my whole life, even if it doesn’t fully “make sense”.
My sense through my work thus far is that when women come into my world, they’re not just interested in mindset or confidence tips. I’ve shared restaurant recommendations with clients planning trips to my favorite cities and recipe picks with clients with similar dietary restrictions.
Of course, I know every client, reader or follower won’t be interested in every piece of my life (nor would I want you to be). But because I can’t know for sure which one of you needs what, I’m choosing to share openly and trust that you all are discerning enough to take what works for you and move past the rest.
Practically, this means that you’re probably going to see masterclasses and products that aren’t so tightly confidence, mindset or dating related. As with all things, you can take what appeals to you and leave the rest. I’m giving myself permission to really explore and this might involve sharing things that feel a little random as I figure out the balance a long the way.
3. I commit to celebrating my own progress and being honest on where I still have to go.
The most empowering thing of working with a coach is, as I shared earlier, often that moment where you realize your goals are more achievable than you realized if you can finally push through xyz thing that’s been holding you back.
Hilariously, the thing is usually (but not always!) more about mindset than logistics.
But I’m committing to sharing wins more openly, even if it feels a bit like bragging, and on the other side of the token, sharing where I’m still focused on my own improvement, because I know how beneficial it will be to show others how you can be both a work in progress and a masterpiece simultaneously.
So here we are. I might be slightly, a tiny bit, a little miniscule amount scared to hit post on this because of what I’m committing to do and the accountability that I’ll then feel held to. But in my heart I feel like this is the right step forward for my business and for me - I don’t know what it will evolve into or where things will go but I’m going to trust that it’s going to take me in the right direction.
And it’s okay if I’m a little messy in the meantime.
Normally, I mention a few ways we can work together at the end of a post, but today’s feels a little to vulnerable to really go there. So instead, I’d just ask you, if you aren’t already signed up for the newsletter, head down to the bottom of this page to sign up and if you aren’t already, follow along on Instagram so you are getting more sneak peaks into the real messy truth that is my life and sampills.co. Thank you for reading!
