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My Inner Critics are assholes.

Since we’ve talked about Sponge Mode, it’s safe to say there’s a lot of material for reflecting during this process.


Journals full of pages of stream-of-consciousness, notes from calls, homework, all of it.

A few weeks ago, I found the article, “How Women Undermine Themselves With Words” and entered the rabbit hole that is Tara Mohr. I read through that post and lost my shit. Then I read another post by Tara, linked in the post about how we undermine ourselves, called “Why Women Criticize Each Other, Plus Ways to Play Bigger” – THEN I clicked through the link to her book, Playing Big. Instant buy.

In the book, Tara enlightens readers with the concept of your Inner Critic (and so much more, but we’re talking about Inner Critics today). That voice inside your head that tells you to take a step back. To not speak up, not publish that post, not talk to that person you want to talk to, or otherwise play small. There are journaling exercises throughout all of the chapters, but starting with the Inner Critic really gave me a new perspective.

Without getting too far into it (I highly recommend the book), the idea is to think about the voices that tell you “no” or “you can’t” or “maybe you should wait.” Then give them a personality. Where are they from? What do they do? Is it a male or female? Why are they trying to keep you from going for whatever you’re going for?

When I thought about this, I had two voices immediately. One female, one male. Taking a few pages from my journal that I’m keeping for “notes from books I’m reading” – I’d like to share a bit about the voices who have kept the best, most fully expressed version of myself locked in a little closet.

The female is a mid-to-high powered corporate type. Workin’ toward that corner office. She’s also a new mom. She wants to keep me in the boat, navigating the waters of office politics. I need to stay in the boat because the boat is the safe way to do things. The water is scary. She’s trying to look out for me, suggesting that I speak when spoken to, since entry-level peeps like me shouldn’t be speaking unless spoken to. Know your role. Keep a low profile. She sees my light, but that shit better be kept under control, I need to establish a reputation, a proper one, and maintain it, damnit. She struggles with her own light. She wants to be a “get shit done” type of high-powered CEO, like those who came before her. But she feels a tug toward taking more time to be a mom. Her expectations of herself – for me – are higher than the skyscraper she works in. It’s a constant battle between hustling to get that promotion (and the hours and travel that comes with it), and spending time with her family. She projects these fears about her career on me. I need to be vanilla. No sprinkles allowed. Lay low, work hard, do as your told, color inside the lines.

The male is an authoritative figure. He’s the sole provider for his family, and he is chasing the American dream of wealth, fancy cars, and all of the THINGS. He’s good at what he does, but it’s not what he really wants to be doing. He’d rather be doing something creative, or outdoorsy, or something that is not a corner office and a suit and tie. He tries to keep me from making “risky” decisions. His whole life has been made making the safe decisions, and he’s doing well for himself and his family, so I should do the same. When I want to pursue something that is a step back on the financial side (instead of going UP UP UP), he pipes up. He wants to make sure I have a steady paycheck, can contribute to my household, and hold my own. When I come to a fork in the road and the two paths are conventional or way outside of the box, he mocks my choices for going outside of the box, when really, he’s punishing himself for taking the “safe” route. “You better not do that, you’re throwing away a perfectly good career.” Safe is predictable and predictable is reliable. Stick with that route.

With these two personalities in mind – people with faces, names, a certain style in how they dress, and a whole life story themselves – the next step is what helps seal the deal on getting clarity on the fucked up stories I’ve been telling myself.

Hear the voice. Say “Hey (name of voice), I appreciate you looking out for me, but I’ve got this covered.”

Let it go.

Get my own voice back. The shiny one. Proceed with enthusiasm.



I spend 50% of my working time doing shit I hate (and I can fix that).

Yesterday, I established that my real unraveling isn’t so much tied to Sydney the ________, as it is looking back on the last 10 years and realizing I did a lot of awesome shit while operating as a very “grey” version of myself. I also mentioned I felt stuck about the direction for Planet Green Socks. How I’m procrastinating on taking action on creating more events.

Let’s dig into that.

Why am I so scared to move forward with events? If it’s not so much an identity thing, then what’s holding me back?

One of the women in my Boss School sister circle, Victoria, is in another program (because SHE’S SUPERWOMAN) and wanted to chat with me about some of the homework/exercises she has for the course.

We hopped on the phone on Friday after our Sister Circle call, and Victoria said:

“I want to ask you questions about your business, but I don’t want to pressure you, given everything we just talked about. If you’re not feeling it, it’s totally cool that we skip this exercise.”

I needed to participate. I didn’t know what kinds of questions she was going to ask, but I knew I needed to hear them and give myself an opportunity to answer them. My usual reaction would be: assume the fetal position, cry, and completely neglect an opportunity to maybe gain clarity. That needed to change.

“Well, ask the questions and let’s see if I can help you out with this.”

She asked me about what I do for an event, from original thought of “hey, this would be badass” to the final emails/thank yous/surveys sent out after the event is over.

She asked about my actual, literal, step-by-step process of how I set up the website, registration, participant profiles, emails, etc.

We used Sun Sessions: Oceanside as the example event. We estimated that I worked 30 hours a week for six weeks making that event happen – from initial ideation, conception, picking the venue, confirming a date, setting up the registration process, all the confirmations/questions/emails about the event, creation of promotional materials, driving out to Oceanside to scope it out before the event, actual promotion of the event, coordinating with the DZ, booking travel for the coaches, negotiating rates, getting participant profiles/registration confirmations, making the event agenda/schedule, sending out relevant information, to actual execution. Then all of the follow up time with paying coaches/the DZ, figuring out refunds, talking with the participants about their options, and finalizing the event.

So say, for 180 hours of my time leading up to the event, 50% of that is the manual checking of registration emails from PayPal, confirming that the participants signed up, then following up on profiles (if they did or didn’t fill it out), additional promotion to fill the remaining slots, etc.

50% of the process that it takes to make an event happen is stuff that I actually, legit, DO NOT like doing. I know it could be streamlined, but I’m all google-drived out and I have my little (free) system in place. Manual checks on EVERYTHING. What if I could streamline 50% of my process? How would I feel about that?

And then it clicked. 

I’m procrastinating on getting more events on the calendar because 50% of the process (and I’m currently a one-woman show on the pre-promotion, registration process, and follow-up), is stuff that is an absolute energy suck for me. It’s necessary, it’s part of it, I know that there are parts of every “job” that aren’t the most fun, but if 50% of the actual manual clicking and typing and moving things around on a spreadsheet could be automated – there is no more room for procrastination.

I know these tools exist. I just didn’t think that an event with 25 people would be worth the spend on any kind of software that could help. I didn’t think I’d be saving that much time (and at this point, time is MONEY for me), and it sounded too expensive.

You know what’s expensive? The amount of time worked on an event (and a small one, at that), and the actual amount of money made. When I did that math before I went through this exercise with Victoria, I was resenting the process. Resenting the system I had established for myself. This was nobody’s fault but my own, and I needed to see that and own it and be open to changing the process. Starting a business is an ever-evolving work in progress. No doubt.

I wasn’t getting to do what I wanted to do: connect with the people who are benefiting from this experience. I want to see their progression. I want to give high fives in the landing area. I want to hear about how they just had the most MEGA jump with the most MEGA coach and their lives are forever changed. Instead, I had set myself up with a “free” system that included a sheet of paper and a pen and keeping manual track of jumps and what load people were on and how many slots we had left and how much daylight we had left (and then inputting all of that into my handy-dandy spreadsheets so I had a permanent copy).

I wasn’t able to be fully present to get the greatest gift of all: seeing the smiles, high fives, and AH-HA moments that these events are SURE to create. 

This week, I’m test driving some event management solutions. There are some powerful platforms out there that do all of the database/registration/payment stuff in one fell swoop. And after actually talking through the process, realizing how much work actually goes into an event, and understanding how I can best spend my time to make these events magical for everyone involved, it’s high time I made some adjustments on how I set these events up moving forward.


I turn 30 in 31 days.

I’ve never really given a shit about how old I was. Actually, that’s kind of a lie.

I gave a shit when I couldn’t drive, couldn’t vote, couldn’t drink legally. I definitely cared about how old I was when I was 12 AND A HALF.

I had a “quarterlife” crisis at 25 – I had just discovered skydiving, it took over my life, and I eventually let go of the identity I had as “Sydney the PR/Marketing Agency Rising Star” – okay not all together, because a lot of my life has been Sydney the _____. Gymnast, cheerleader, rowing team walk-on, Jayhawk, USF Alumni, PR/Marketing Gal, Analytics Gal, Skydiver, Competitive Skydiver, Event Coordinator, blah blah blah. Lots of taglines.

So yesterday, right before I hopped on my weekly Boss School sister circle call, I found this post written by my friend Nicole.

For the past few weeks I’ve been all over the place. Breakthroughs. Breakdowns. Frustration. Elation. Both ends of the spectrum and everything in between. It’s like I’m on a see-saw and it’s either flying up, or floating back down to the ground. Both sides. All of it. Maybe because 30 is looming. Maybe because of the self-development stuff we’re working on in Boss School. Maybe because the universe is weird and the moon’s about to be full.

I feel stuck. I’m terrified to take action. I know that what PGS is all about is going to change from where it’s at right now. I’m not sure on the HOW yet, but the WHY is most certainly clear.

When I read Nicole’s post (if you haven’t read it yet, feel free to do so and come back so the rest of this paragraph actually makes sense), my initial reaction was as such:

If you replace “drinking” with “skydiving” – this post IS MY LIFE RIGHT NOW. I haven’t jumped since the end of last year, and before that, I hadn’t been jumping with any regularity since June, at least not hammering out jumps like I was when we were training/competing. So I’m creeping up on a year of borderline-uncurrency. So, for the sake of talking, I “quit” jumping. So I’m pretty much the “non-skydiver” in all of the situations where Nicole was the sober one. I go to the events. I hang out with all my skydiver friends. I MAKE events happen, but I’m not participating (which, by the way, has always been my preference). Is this scary because I’m done skydiving? If I’m done skydiving, what is my tagline? If I’m not “Sydney the Skydiver” – a part of my identity for half of my 20’s – some serious years of growth and development of who I AM – then who am I? Did I go through this when I left the agency world? I can’t remember. Fucking brain. 

This was my topic of discussion with my amazing Boss School sisters. Who am I? What the hell am I doing with my life? How can I give something that matters? What’s the next chapter? If I “officially” quit jumping, do I still have skydiving friends? Am I still fun to be around? Do I still bring value to my skydiver friends’ lives even if I don’t jump out of planes anymore? WHAT DOES IT ALL MEAN?

I feel stuck. Unable to take action with what needs to happen with Planet Green Socks. Procrastinating on taking action. Is it because I’m “done” with skydiving? Has this sport served its purpose for me? Is it time to let it go? Is that giving up or is that recognizing when something is no longer serving you?

My sisters heard me out, and gave me some clarity after vomiting the internal monologue above in one breath. They’re so patient with me when I’m on rapid fire mouth diarrhea.

“What if you’re just Sydney, and that’s enough?”

I let that sit for a bit. My brain started rapid-firing (29 years of conditioning to analyze, sort, and file information), so I took some deep breaths to slow it down.

Well, that certainly sounds doable.

Jess, one of the women in the group, also turning 30 this year, summed it up perfectly:

“I’m not so concerned about turning 30 and where my life is at vs. where I thought it should be by now. I’m more concerned about looking at my 20’s and wondering why I wasn’t comfortable being me.”


When I think about turning 30 in 31 days, I’m not uneasy about the number. My life has completely changed from the plan I had when I was a little girl, when I was in high school, college, my first job, after my first skydive, even in the last 8 months, it’s a completely different picture now than it was when I was thinking about what it’d be like.

I’m not worried about that.

Like Jess, when I think of 30, I think of a new decade. I look back at the last (almost) 10 years of my life and the only thing I can say is this:

I wonder how my life would be different if I hadn’t been shushed by others and shushed myself and dimmed my light and turned down the volume on my voice? 

I don’t stay in that place for very long, that place of wonder and borderline-regret. I focus on the things I’ve DONE so far. I made some BIG decisions in my 20’s. I moved to Florida (almost 20, but whatever), I chose to take a year off of college to work at Disney. I changed from Pre-Med to Mass Communications. I went to SXSW. I got a kickass job at a kickass agency before I graduated and moved to Chicago. I spoke at SXSW. I went skydiving for the second time. I let that sport take over my life. I moved to Austin. I spoke at SXSW again. I gave myself permission to make love a priority. I let skydiving take over my life some more. I moved back to Illinois, away from the security of a “real” job. I moved to California. I got married. I quit one of the best jobs in the industry to go out on my own.

I did all of that, completely muted. A grey version of my bright, shiny, sparkly self. There were brief periods of time where I let my light shine, only to throw that version of myself back in the dungeon under lock and key.

If I could do all of that in my 20’s without my true, fully expressed self/voice/light, I can only imagine what my 30’s will bring.

If all of that was possible when I was still holding myself back, and now I’ve committed to myself to let the light shine, turn the volume up and let my voice be heard, the next decade is limitless.

More importantly, this is something I want to share with women everywhere. My WHY is perfectly clear – I want to share this story, share these experiences, and let women everywhere know they are NOT alone. That the little voice inside that wants you to play bigger needs to be let out and be heard. That when you give yourself permission to be REAL – the world just kind of unfolds into whatever you want it to be – and everything around you changes, for the better.

So the WHY is clear. The HOW – now that’s the ticket. HOW can this get out there? HOW can I share this? HOW can more women get a voice and tap into the power they know they have but don’t feel comfortable expressing?

That’s what I’m open to finding out. For the first time in 29 years (or however long I’ve been consciously making decisions), I’m letting go of the analyzing/sorting/filing process – the part of my being that NEEDS ANSWERS RIGHT THIS SECOND. The HOW will show up. And I’m excited to see what that means for me, my expression, the people in my life, the way I fucking show up and give fear the middle finger, and inspire/enable other women to do the same.

30 sounds really, really, really good.




Sponge Mode: Activated.

I’m going to let you in on a little secret: Boss School is, without a doubt, the most insane experience of my life to date.

More insane than jumping out of an airplane.

Since the course started at the end of March, I have had so many lightbulb moments, so many breakthroughs, so many insanely powerful moments, and more than anything, a lot of confusion.

Stick with me here.

Sun Sessions: Taft was incredible. Everything worked out and we were almost at full capacity by the time the weekend actually came around. The event, overall, was a smashing success.

So why then, on Monday/Tuesday following the event, did I feel like complete and utter dog shit about what the hell I’m doing with my life? Surely this is all “too good to be true” and the Universe will all come crashing down, because there is no way that this could possibly be real life.

This is the story I’ve been telling myself, along with some other pretty fucked up stories. Without rewriting the pages of my journal verbatim, this is a quick dump of what went through my mind in the last couple of weeks.

Sun Sessions was a hit. YAY. Should we do it again? Yes. Do I like traveling? Not as much as I thought I would, at least not without Barry and the dogs. But you said “we execute professionally organized events all over the COUNTRY, not just Southern California” – you better hold up to your little tagline there, sister. You hyped up the fact that this was going to be a road show and now you decide you don’t really like going outside of your comfortable little bubble in SoCal, wow, you’re a hot mess. Here, call your mother and talk to her about all the times you’ve limited yourself, been “shushed” and didn’t let yourself shine. Wow, you have a serious pattern of self-sabotage – how does that feel to uncover? Oh, you mean you were raised in a loving home and really were taught that you can be anything you want to be – what kind of fucked up “friends” told you otherwise? More importantly, why did you believe it? You have a history of listening to people that actually, legit, mean nothing but harm for you, why are you so cool with that? Why do you tolerate it? WHO ARE YOU AND WHERE DID YOUR VOICE GO?

The exercises in Boss School have uncovered a whole slew of shit I didn’t know I was feeling, thinking, doing, tolerating, expecting, or putting out there. I signed up for this course completely sure that I’m a self-aware little lady and that by the end of it, I’d have a framework for the “how to run a business” side of running a business. But noooo, the first 4-5 weeks are all about the foundation of my business: Me. Sara wooed me with all the answers I need about legal and funding and marketing and financial stuff, and then was like, “Oh hey, by the way, we’re going on this journey into the depths of your (apparently long-time silenced) soul and we’re going to make sand castles in there and blow shit up, cool?”

YES, actually, it is cool, Sara. Thanks for taking me to places I didn’t know I needed to visit, because I didn’t know they exist.

I’ll spare you the details of what Brene Brown would call an unraveling from the last three weeks, and tell you this much: I’m in serious Sponge Mode.

Sponge Mode is what happens when I get fired up about something: working in restaurants, marketing, PR, skydiving, event planning, etc. The topic of Sponge Mode activation: this seriously deep inner work journey thing we’re doing.

With Sponge Mode, I want to do ALL OF THE THINGS related to the topic. I want the books, the experiences, the language, the jargon, the knowledge, and most importantly: THE ANSWERS. My brain goes into hyper mode and starts trying to analyze, classify, sort, and file all of the information, breakthroughs, lightbulb moments, etc. It’s a tidy office up there and we can’t have all of this clutter lying around.

Good news is, now I know that Sponge Mode is a thing. This is how I’ve always gone about my life. Absorb, absorb, absorb until I’m at max absorption capacity. Then I have answers. And then I make big life decisions. And then things always line up super awesome and tidy and I run, full-bore, into my new thing, whatever the new thing is. I now recognize this pattern of Sponginess and I can see it coming.

Sponge Mode is rad in itself as far as getting into whatever I want to get into – but the way my brain sorts through shit that I need to be wary of. I’m learning so much about myself in this process that I feel like it all needs to fit on this little timeline so I can draw as many over-analyzed conclusions as humanly possible.

I got a friendly reminder last Saturday at a workshop to just slow the fuck down. This whole thing is a process, a journey, and part of figuring out who I am, where I’m going, and what sweet sweet gifts I’m going to give the world before I leave it. If I could sum up this journey so far in a few words: I need to give myself permission to experience this. My brain keeps trying to get in the way because it’s been ruling my world and my story for FOREVER and I just need to sit down, shut up, and feel it out.

This isn’t a mess that needs to be cleaned up. This isn’t a stack of papers that needs sorting and filing.

This is the start of something new, powerful, engaging, and to be quite honest, terrifying.


The CSC-to-Elsinore crew, circa 2013.

Why I want to see you on May 16, 2015.

I’m going to be 100% real with you here. And it might be messy.

If you only come to one event that Planet Green Socks puts on, I want to see you at Skydive Elsinore on May 16th for Adam Rubin’s memorial.

Chances are if you read this blog (and THANK YOU FROM THE TOP MIDDLE AND BOTTOM OF MY HEART FOR READING), you already know about the influence Adam had on me starting Planet Green Socks.

If you don’t know, let me tell you. Adam’s death lit a fire under my ass to start this business. I used to feel borderline guilty for saying that, like if he didn’t die, I wouldn’t have started it, but I can’t be sure that I would have. His ripple effect is way bigger than I can comprehend.

Can you relate to any of this?

  • I am tired of doing what I’m doing.
  • I want to wake up and feel ALIVE – full-on, balls-out, ready-to-tackle this day ALIVE.
  • I want to to that one thing I’m fucking terrified to do – make a change in my career, have that hard conversation I know I need to have, try a new hobby, etc.

If you join us on May 16th, I can personally guarantee you’ll walk away with some kind of inspiration to do change whatever needs changing, fix what needs fixing, or keep doing what makes you awesome. The inspiration might show up in many forms:

  • Hugging Adam’s mom, Linda, and FEELING the love she had for her son and the love she continues to have for the skydiving/BASE community that took Adam in with open arms. Her hugs are legit, and I felt that the first day I met her, and haven’t forgotten it since.
  • Meeting Adam’s sister, Nicole, with her gorgeous blue/purple hair, SICK tattoos, and hearing her speak of how Adam made her feel and how he’s inspired her to chase her own dreams.
  • Speaking with his aunt, Kathi, and watching her eyes twinkle when she remembers his big megawatt shark smile.
  • Watching two of Adam’s friends, mentors, teammates and fellow skydivers, Eric and Don, as they plan and execute a beautiful memorial skydive. Seeing the raw emotion before and after that jump, as canopies join together in the skies to say farewell to one of the brightest shining lights to ever set foot on the grounds at Skydive Elsinore.
  • Seeing people join together from around the country to celebrate the life of a young man who was taken far too soon, but made a huge impact on the life of everyone he touched. That’s a special gift to have – to have everyone feel like your best friend from the second they meet you.

If you join us on May 16th, regardless of whether or not you knew Adam, I can promise you’ll understand why this is such a big deal. Why he is such a big deal. Why LIFE is such a big deal.

I started Planet Green Socks to change the fucking world. The events are here to serve to Adam’s legacy and are built on things he definitely enjoyed: Adventure. Community. Growth. Losing Adam was the catalyst to a major journey of self-discovery. Letting my light be seen and my voice be heard; two things that were beaten down, squashed, and hidden to avoid upsetting the apple cart. I wish I could have gotten that courage when he was still with us, but I am so thankful for the opportunity to call him a friend and have him be a part of my life. A HUGE part of my life.

So if there is one thing I can ask of you, just one, it’s to show up on May 16th, regardless of whether or not you knew Adam.

If you knew him, show up to tell Linda, Nicole, Kathi (and all of this friends) how much he meant to you. Tell a classic Adam story. Keep his memory alive and his legacy strong. Share what it’s been like for you. We’re all in this fucking thing together and there’s no right or wrong way to get through it. Share it. Give me a hug too, because I’ll be feeling ALL OF THE FEELINGS and can definitely stand to have some support as well.

If you didn’t know him, chances are you already know someone who did know Adam. Come to support those people. Show up for your friends who are (finally) able to gather and give him the skyfamily sendoff he deserves. If you take nothing else away, I know you’ll feel inspired to take a look at how you “live your dash” (click that link and read it) and impact the world around you.

We have a limited amount of time on this planet, so let’s use May 16th as the perfect opportunity to enjoy that time. To hug our people NOW. To tell someone how they’ve inspired you or how much they mean to you. Let’s get down with the messy and beautiful parts of life and just let ourselves be seen, for Adam. For our friends. For ourselves.

If you need another reason to join, my best friend and one of the people who helped me make it through 2014 in one piece, Katherine Humphus, will be cooking dinner for everyone that night at the DZ. We’ll be collecting donations for the Adam Rubin Memorial Fund, an account that Linda and I are working to establish with a facility that specializes in treating Crohn’s Disease. Even with insurance, the treatments necessary for Crohn’s patients to best manage the disease are several thousand dollars. With your help, we’ll be helping those patients get the treatments they need to live WITH the disease, and to live HUGE like Adam did. We’ll be collecting donations on site, but if you can’t make it to Adam’s celebration or you can’t wait, you can donate online by clicking here.

I look forward to seeing everyone come together to celebrate the life of one of the most influential people to ever walk into mine. If you want more information on the nitty gritty about the event, you can find that by clicking here.