Startup Weekend Unwind

I’m sure you can quickly recall a moment when you didn’t feel prepared, or were worried about being good enough to pull off a big project. This is a story about that.

This summer our office attended a Startup Weekend. About a week and a half before our departure, our fearless leader (Jason Sasso) emailed an itinerary to our office. I read through it all with enthusiasm and an eye for detail.

A phone call to Jason went something like this:

Me: Ohmygod I think I’ve gotten myself in too deep, this seems really intense, this is a bigger deal than I thought. What should I be researching, what books do I need to read, how can I cram before this?!

Jason: Cool your jets, you’re gonna be fine. You have more to offer than you give yourself credit for. You bring wonderful and new perspectives to every project. You’re gonna be great.

Me: But, but, but..If you say so. *mumbled sounds of worry*

At Camp BluSky

After arriving to Camp BluSky for our event we chose teams and settled in. I quickly realized my team really didn’t have the skillset we needed in order to pull together a full business proposal by the end of the weekend. As I researched our proposed gadget I found it already existed. As I tried to improve upon the current design, I realized I had no idea how to do that. I had chosen a cool idea to hop on board with, but we just didn’t have what we needed to make it work the way I wanted or expected.

Jason was great. My coworkers are amazing. Always positive, always giving me gold. Always making wonderful suggestions. The mentors for the weekend were doing the same.

My brain was spinning, I was feeling overwhelmed and worried about flopping. Admittedly, I was making a bigger deal out of this than what it needed to be. But uh… that’s what happens when you’re a perfectionist. For better or worse, you put that pressure on yourself. I went to bed quite worried about how the rest of the weekend was going to pan out if I stayed with the team I had chosen.

What I Learned

You know what I learned? I learned it’s okay to know your limits, take a break, and decide to leave. It’s totally ok to switch teams, because it’s really important to be matched with people that can utilize your strengths and help bring out the best in you. I greeted the morning with determination. I respectfully switched to a different team. This is totally kosher, and happens a lot.

Camp BluSky Startup Weekend


My new teamies greeted me with smiles and love. They were lively, full of ideas, eager to do the work, AND had done startup pitches before. Yesssss! It is amazing when you find your fit. I felt a lift in my step when I found a better team for myself. The people you surround yourself with, the energy you gather from your team (in all areas of life), impacts the way you work in the most outstanding way.

You guys, this is a metaphor for life. When you come into any situation (whether it’s in work, school, a relationship) and it feels scary, you feel unprepared, you feel like a doofus… it’s good to put in your best effort. And, it’s good to know your limits. Take a deep breath and surround yourself with environments that bring out all the best in you! Because, I think you’re probably more awesome that you even know.

Finishing the Pitch

Time management can be a beast in normal life but this event really takes it to a whole new level. When you’re put into a large group with wonderfully intelligent thinkers and idea-havers, sometimes it’s tricky to stay on task. I sometimes felt like I was herding squirrels in a peanut factory. I was often reminding everyone of tasks at hand and the ever waning countdown to final pitches. At other times felt like I was a student amongst a tribe of gurus. I was often taking back seat while they organized financials and created in CAD.

All in all, the spirit of this group was just phenomenal. We’d found a dance and a balance with one another that allowed us to have fun in the midst of a difficult project. I once read that a characteristic of lasting relationships is being able to laugh in the middle of a big fight. The ability to see that even though this might be hard and stressful, there is definitely a happy end in sight. Everyone was so supportive of one another, upbeat, a real “we can do this!” attitude. I have to admit, I was the Negative Nancy more often than I would have liked. Because, you GUYS, we’re running out of time!

During the final countdown I was asked to present the final pitch for our idea. Honestly, in that moment, I was hesitant that we’d actually be able to pull it off and have a decent presentation by the time we needed to. My teamies praised me for helping everyone stay on task, and by golly, by the skin of our teeth, we totally pulled off our pitch. We totally did it. (And yeah, I helped pitch it.)

Coming out the other end of the weekend, I feel completely humbled. I feel bigger, and stronger, and braver for it. My team, my office of humans that see me for so many hours every week, have now experienced a version of me that I think a lot of us work to hide. There were moments where my anxiety was pretty high and I was totally checking out. In my head I was questioning whether I could be successful at this. I knew they could see it on my face. I don’t know if they realize it, but this event was hard for me and I felt so vulnerable to have these humans see me on the ride.

But uh..real life is a ride. We want our offices to be places we come to be experts at things. We are “Social Media Marketing Gurus” and “Executive Directors” and “Designers” and “Specialists”. We have our lives together, and these lives don’t impact the work we do inside the office walls. In this space we have answers, we have solutions, we finish projects, we meet deadlines, we don’t have problems, we don’t have issues. Or at least that’s what we strive for and want everyone to think, right?

But let’s remember that we’re real live humans. We can be honest and real about the fact that sometimes our separate worlds impact one another. And guess what? Even when there are bumps in the road, everything still works out just fine. Projects still get finished, pitches still get made, and the camaraderie that’s born out of working hard together is completely priceless.

If you sometimes feel worried about being good enough and pulling off overwhelming tasks here are some more suggestions from a successful newbie:

  1. Research your project! But, give yourself a limit on how much time you’re willing to put into your research before starting in on whatever your project is. If you’re like me, the more you know the more you’ll realize you don’t know and you’ll get totally overwhelmed. At some point you’ll have to jump in, but having a toolbox of information to draw from might be helpful. Also, know that there will definitely be others there to help you. You can always lean on a friend or coworker for extra input.
  2. Set your intention! Are you here to learn? Are you here to win? Are you here to party? Taking a moment to prepare yourself for what you’re coming into, and what you’re hoping to get out of it will help you feel more prepared to greet whatever comes your way. Now, throw half of that down the drain and just go with the flow. Take a deep breath, and chill out. Let go of hard expectations. Like they say, “You make plans, and the universe smashes them.” … or something like that.
  3. Be less cool! Better yet, just be yourself. When choosing a team, friends, new job, partner, or anyone else you’re going to surround yourself with, think less about how cool they are and more about how your skillset, knowledge base, and the things that make you unique will be utilized toward success. Will you feel appreciated, smart, well utilized? Will you feel like you can be the best version of yourself? Will you be welcomed for who you are? Sometimes we realize we’re just not a good fit, and that’s great! Because then we get to continue our adventurous search for the good fit.
  4. Mindset and attitude! When a project or problem feels overwhelming, reframing it in your mind can make all the difference. At Startup I pretended I was back in school. It felt like I had left my entire semester project to the last minute and had 36 hours before it needed to be presented to the prof. and entire class. With that mentality, somehow, everything felt totally doable.
  5. It’s okay to peace-out for a minute! Seriously. I’m someone that wants to always plow through issues and work that comes to me. I don’t want to leave a situation until it’s resolved. But, sometimes you just have to. You have to get up and go for a walk. Get up and have a beer. Get up and tell a joke. Relax. Deep breath. And then get back to it.
  6. Know that you ARE good enough. Or, fake it until you make it. There’s something to be said about Bill Murray’s tactics in What About Bob? Telling yourself, “I feel good, I feel great, I feel wonderful!” or something similar, actually does help your brain believe it. Google it, there’s empirical evidence to prove it.

SWELL team goes to Startup Weekened

(That’s me. Pitchin’ like a pro.)