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Lessons from putting myself out there
Yes, it’s as cringey as you’d expect 😂
💌 What’s happening this week:
Lessons from putting myself out there
Journaling prompt:
If you can’t beat AI, might as well learn how to use it?
May Plan With Me (yes, one month late 😅)

“Lessons from putting myself out there - yes, it was cringey and sometimes I feel a fool”
Last Sunday, I…
Spent 10 hours outside
Under the Toledo sun
At the Rastro Literario, hosted by two community groups in the city
To sell…
Drum roll, please…
6 ITEMS 😂😂😂
wait, let me laugh a little more LOL 😂😂😂
Ok, now that I got that good chuckle out of the way…
I have more thoughts about this event, but I’ll be sharing them in next week’s vlog about my experience preparing for my first-ever market and what it’s like to sell in-person, D2C, and handmade…
👀 HINT: Very different than running an online, location-independent marketing and media agency serving B2B clients.
But what I wanted to talk about today are some of the lessons I learned from putting myself out there in a totally different setting than what I’m used to.
To give you some context, I have grown my entire brand around being ‘location-independent’, straddling the United States and Spain. I’ve also grown an entire business (and lived off of it!) strictly offering digital services and products that can be done anywhere in the world.
While I’ve also been living in Spain for a total of 10-ish years, in Toledo for almost 4, cultivating local community can be very difficult. I would say in Madrid it was easier to find community, although the majority of the people I did meet were other foreign folks who were also transplants to the city.
In Toledo, well… it’s a totally different game here.
Toledo is a smaller city than Madrid, it’s much slower-paced, and has a traditional rhythm to it… meaning, you gotta know people to know people, to do things, to meet people, and to integrate yourself.
While it’s been more of a challenge to integrate myself into local communities and take part in different initiatives, I’ve been really trying to put myself out there more and look a lil’ cringey all in the name of BELONGING (and yes, just trying new things and growing as an individual).
After my market experience, putting myself out there in a different setting reminded me of what it’s like to also put yourself out there to make friends (and as an adult, it’s awk)!
Here are the lessons I was reminded of after my in-person market experience:
🙈 MOST PEOPLE DON’T CARE
It was my first time being a vendor, setting up a booth, and even doing something so ‘front-facing’ in the community. I felt a little bit of imposter syndrome because I really had no idea what I was doing. I also felt like a fraud because “I’m not a maker, I’m a marketer”. But when I was standing there and talking to my stand neighbors, no one cared.
No one cared that I had ‘another job’, that this ‘was my first time’, or ‘I have no idea what I’m doing’. They were in their own world and just wanted to get to know me and chat! Most people didn’t care that this was my ‘first time, either; they were actually very encouraging and excited for me.
💡 BE PROACTIVE
Marketing online and not seeing ‘engagement’ in terms of likes, watch hours, clicks, or open rates is one thing. I feel like it still stings when no one sees your content or ‘buys from you’ when you launch a product, service, or course… but whoa, it’s a different feeling when someone comes to your stand, browses through your products, and then… leaves without buying and doesn’t even say “Hola” back! 😅
I learned that being proactive in both instances (marketing online and in-person) is HUGE. Being the first to say hello, engage in conversation, or invite someone in has helped me put myself out there, meet new folks, and even sell or get my foot in the door for opportunities.
🎀 MORE PEOPLE ARE SUPPORTING YOU THAN YOU THINK
More of a reminder than a lesson for myself! Sometimes I think we get in our heads about ‘putting ourselves out there’, like it’s so EMBARASSING... cringey… We’ll look a fool… no one will support us. And yes, sometimes, it is embarrassing and cringey! Sometimes, you will look like a fool because you just don’t know, and you’re doing something new!
But what I learned on Sunday was that more people are supporting you than you realize! People are watching and they’re taking note when you put yourself out there! I experienced this firsthand with my network and y’all, I FELT THE LOVE AND SUPPORT.
My partner supported my wild idea to be a vendor. He helped me bring all my supplies and inventory, picked me up, and stopped by midday to bring me lunch and hang out. I had friends stop by to keep me company during the 10hr shift, asking if I needed water, snacks, coffee… and a whole group of friends who hung out for a few hours behind my booth to chat, ‘fake browse’ to bring in clients (lol!), and even bought some of my handmade bookmarks. Aside from my close network, I had folks compliment my booth setup, wish me good luck after I shared that AI took my job (😅), and even more.
While I only sold 6 items last Sunday, I am proud that I put myself out there in a different setting, started building connections with local community, and had fun while doing it!
Allz this to say, putting yourself out there brings in WAY MORE than if you stayed in your head about something you’ve been wanting to try. What could you do this upcoming week to put yourself out there?
Oh, BTW, here are some snapshots of my booth at the Rastro Literario! I love how it turned out 😍
✍️ THIS WEEK’S JOURNALING PROMPT
“If I knew I could not fail, what would I do right now?”
Ah, a CLASSIC journaling prompt I turn to whenever I get in my head about trying something new, putting myself out there, or wanting to create some type of change in my life.
Well, if you knew you couldn’t fail… what would you do right now? And forget ‘how long it would take you’ to do that thing… if you knew you wouldn’t fail, would you try anyway?
💻 THINGS THAT STUCK OUT TO ME ON THE INTERNET
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🗓 PREPARING FOR THE WEEK AHEAD
📅 MONTHLY REVIEW & RESET This past week, we hosted our May Monthly Review & Reset inside the Plans to Progress Lounge. I love hosting these monthly sessions where the community comes together to share how the month went, what came up for them, and any notable things they’d like to remember or learn from! Here are a few questions I share with folks:
ahem, those are extra journaling prompts for ya 😜 In the Lounge in June, we’re having a mid-year reset retreat, a 3-day virtual retreat to review the 1st half of the year and plan for the 2nd half. Join us inside the Lounge to attend the retreat and all our community events! |
🌻 GOODIES YOU MIGHT HAVE MISSED
Plan with me in my bullet journal for May! 🌱🍒🌷 Originally, this video was supposed to go out beginning of the month, but life kinda happened… so really, it’s a chatty catch-up with me, while I plan and set up for the month in my bujo. You’ll get to see how I migrate important dates and tasks from one monthly set up to the next (:
🤝 HOW TO WORK TOGETHER
Want to work together to create time and space for intentional connections? Here are a few ways to do that through marketing support, journaling, and education.
📓PLANS TO PROGRESS MEMBERSHIP: A quarterly membership for big dreamers to intentionally plan each month with the accountability to transform your ideas into actionable steps and projects. Join us inside the Lounge here!
⭐ SIGNATURE BRAND & WEBSITE DESIGN + COPYWRITING PACKAGE: Get 2 brand strategists on your team to elevate your brand visuals, website, and messaging. We have 2 spots to start this summer. Learn more and apply here.
👀 WEBSITE AUDIT: DIYed your website copy and want to get an expert’s feedback and edits? Book a Website Audit and get feedback on what’s working and where to improve in just 2 weeks.
Can you believe we’re already in JUNE, friend?!
I don’t want to say “where did the time go?” But… really, where did the time go?! 😂
I can’t wait to share with you all of the things I’ve got planned for June, vacation included!! But of course, until next time…
💖 #stayfierce,
Cassandra
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