Note from Paige:

I absolutely L-O-V-E hearing from past students of my Square Secret™️ & Square Secrets Business™️ courses!

1) Because I’m genuinely tickled to hear that they are out there crushing it and totally owning their dreams!

Annnnd…

2) Because no two stories look exactly the same, and they are constantly blowing me away with unique nuggets of wisdom they’ve picked up along the way.

Legit so inspiring! And it would be crazy-selfish of me not to pass those bits of encouragement and advice on to you!

So in today’s post, we will be hearing from uber-talented past student and designer, Katelyn Dekle of Launch The Damn Thing!

But before I turn Katelyn loose…can we quickly talk about how she is already booked MONTHS in advance, and bringing in way more than what she did at her 9-5? (All while rocking her new-found locational independence & scheduling freedom!)

Oh, and how gorgeous are these recent designs of hers?

Dear web designer…

Playing it safe is keeping you from your dream life & business

By Katelyn Dekle

If you’re standing on the precipice, afraid to take the first step, –OR if you’ve been plugging away at this thing called “business” for too long and still not seeing any traction? Then I’m talking to you.

Yes, both of you –all of you, because you could be either OR both at the same time.

How do I know? Because I was there too and now I’m dying to be that reminder you need in order to get out of that headspace so you can actually start hitting your goals.

I started my freelance work –I won’t call it business, because that’s not how I thought of it back then– 6 YEARS before I actually left my full-time job.

And real talk: I only left because I got furloughed during the pandemic.

That furlough was the best thing that ever happened to this risk-averse, comfort-zone-expert because I’d been playing it safe. Like, safe-sex-is-no-sex safe, –or safe-risks-are-no-risks.

I kept the 9-5 while I was “building” my freelance business because the steady paycheck made me feel “safe,” and frankly, we just really couldn’t afford for me to just quit (queue: risk-aversion). That’s the normal, “correct” thing to do which everyone assumes is the right thing to do… (ie: don’t do anything stupid, like stop getting steady checks to pursue your passion!)

However, aside from helping us to continue paying all of our bills on time, it also sucked up my time, creativity, and energy, forcing me to work on or learn about freelance stuff during nearly ALL of my free time. For YEARS. That length of time in & of itself is not bad, but…

What’s the number one way to have marital problems & make your partner feel like your absolute last priority? Start your own business with a single-minded focus on it above all else, mostly ignoring him/her for months on end and simultaneously telling them that “it won’t be like this forever” even though it was obvious to him that it would be. #guilty

I did that because it truly felt like do or die to me.

I was and had been so miserable at my 9-5 that I knew if I didn’t make my freelance business a success, I could never leave my day job and become the person I desperately wanted to be: a much happier, less stressed, financially successful person.

I cried a lot during those years. I felt SO trapped. Stuck. Stilted. Unappreciated. Overworked. Undervalued. Misunderstood. Ignored. Confused. Overwhelmed. …Depressed.

I was burning out, pissing off my husband unintentionally, not taking care of myself, and what did I have to show for all of that? About $10k/year on a good year; all of which I was investing right back into the business to learn more because I didn’t know “enough.”

But the truth is? I wasn’t successful freelancing, because I was playing small.

I was playing NOT to lose, instead of playing to win –and there’s a BIG difference.

If you’re just playing well enough to make sure you don’t lose or come in last place, that is NOT the same level of effort required to win or come in at first place.


Let’s back up for a sec. I’m an Enneagram 6 (Loyalist) with a 9 (Peacemaker) and 3 (Achiever) wing, in that order. I’m a “White” in the Color Code personality test, and an INFJ-T (The Advocate).

Not into personality tests?

All of that means I’m a rule-following, risk-averse, loyal, high-achieving, peacemaker that LOVES my comfort zone and prefers to be in the background helping everyone else but herself.

That combo makes it very easy to play things small and:

  • To not want people’s attention on you.

  • To not want to risk scary things like not being able to buy groceries or pay your bills.

  • To not want to be a failure.

  • To not want the well-meaning critics/naysayers to have reason to say, “I told you so.”

It makes it hard to learn how to stand up for yourself and not take other people’s sh*t, too.

I’m not saying that being able to pay bills, rent, and buy groceries aren’t real things and I’m definitely not saying those things shouldn’t be a very real consideration because we all have to eat and we all have to have shelter. I get it.

But if those considerations are where you get stuck and you STOP there? You’re focusing on the wrong things.

Stop thinking about what you’ll have to give up or what might go wrong…

…and start focusing on what you could get and what might go right!

One thing I know: the law of attraction is real. We are what we think and do. Like attracts like.

If all you ever think about are the what-ifs of utter failure, then that is exactly what you will create for yourself. If that’s you, then you are spending all of your time and energy looking for ways to count all the negative things in your life, keep track of them and use them as excuses for why whatever you’re doing isn’t working or going to work. That also means you’re missing all the positives because you aren’t looking for them!

On the flip side, if all you ever think about are the successes you will have, the progress you are making and the growth you are experiencing, you’re actively looking for positivity in your life which means you WILL find it.

So if you think your only option is to play not to lose, how do you switch gears and start playing to win?

Ask yourself: “how would I act if I was already successful?”

If your kneejerk reaction was to say, ‘I have no idea’ then sit with this for a minute. What would you NOT do, if you were Oprah Winfrey?

  • Keep your 9-5 job for security reasons…

  • Be afraid to tell other people what you’re building, because you don’t want to be judged…

  • Be so afraid to fail that you never actually get started…

  • Don’t charge enough, because you don’t “know enough” yet…

  • Let your imposter syndrome guide your decision-making…

  • Be afraid to tell clients the price to work with you, so you always offer unnecessary discounts…

  • Hesitate to take challenging work because you didn’t think you could make the client happy…

Right? The successful Oprah that we all know & love wouldn’t dare do any of those things! She may have acted that way in the earliest of her career, but the key is to realize that at some point? She stopped doing all of those things.

So, read that list again (I’ll wait). Now, if you were ALREADY the best at what you do, would you still do any of it?

Are you shaking your head, “no?” Then why are you doing it? ‍♀️

I get it. It’s terrifying to do something new and unfamiliar and scary and risky…but the things we are MOST proud that we’ve overcome are never the things we did from our comfort zone.

I was never fully “proud” of my freelance work while I had my 9-5 because it was my comfort zone. I didn’t feel pride that I was in a concert band in grade school, because that was in my comfort zone. I felt ‘average’ about moving away to a college that was a hop, skip, and a step from where I grew up because it was in my comfort zone.

But I do feel proud of my business now that I’ve completely replaced my 9-5’s income within the first year I’d begun working full time in my business. I did feel proud of my flautist skills after I had successfully played several flute solos while in that concert band (the kind where everyone in the entire auditorium is looking at YOU and can only hear YOU). I did feel proud of myself when my husband and I moved 1,300 miles from home to a state, city, and house we’d literally never stepped foot in before, just because we wanted to try someplace new.

Get started by changing these 2 small words.

I’ve been reading (and re-reading) The Middle Finger Project, by Ash Ambirge. I’m not an affiliate for it or her, but it was recommended to me by a business coach friend of mine and I ended up devouring it.

I actually bought the Audible audiobook, …the Kindle book shortly after I started the audio so I could highlight the absolute hell out of it, and when I finished? I bought the hardback too, just so I could see it on my bookshelf in my office.

She said something in the last few pages that really smacked me in the face:

“The difference between someone who becomes a victim of their circumstances and someone who rises despite them, then, is that tiny little word right there: despite. Moving forward despite your past, despite your fears, despite your doubts, despite the struggle, despite it not being what other people think you “should” do. It’s the opposite of doing things because, which is how most of us live our lives. We do this because of that. We do that because of this. We don’t leave jobs we hate because we don’t know what we’ll do next. We don’t try new things because we don’t know if it’ll work out. …

…But what if you tried a different approach? What if you left the job you hate, despite not knowing what you’ll do next? What if you tried something new, despite not knowing if it’ll work out?” 

–The Middle Finger Project by Ash Ambirge, pages 269-270 (Kindle edition)

And as Ash says in her book, choosing to live your life and make decisions “despite” instead of “because” –it changes everything. You become “radically self-reliant” and start making decisions that WILL move you forward, instead of setting you back or keeping you stuck exactly where you are.

I know, I know.

I can practically feel your resistance to this right now, even though you don’t want to feel it. That resistance you’re feeling is GOOD though. Opposition is often required to be successful. Think about it: airplanes need both thrust and drag in order to fly, –and so do you.

If you’re thinking, ‘but I want to do it the right way’ and that’s what’s stopping you, then hear me when I say there is NO right way to do anything for everyone. There is NO perfect way for everyone to do anything.

Your website? It will never be perfect. Your business? It will never be perfect. Your knowledge or skill-set? It will never be perfect.

There is always room to pivot, grow, change, evolve, and develop.


For the love of all things holy, do NOT wait until you’re “ready” to start.

The quickest way, and the only way I can absolutely guarantee that you WILL FAIL is to wait until you’re ready. To wait until you know enough, are comfortable enough, have enough software, bought enough courses, developed enough confidence, have enough savings, have enough help, have enough time…

You either move forward, –or you don’t. It’s that simple. 

So if success is what you want, if growth is what you want then you CANNOT stand still. You CANNOT play small. You CANNOT be stagnant. You CANNOT wait until you’re “ready” because the truth is you may never “feel” ready.

When you take a step forward into unknown territory (yes, outside your comfort zone), you have no other choice but to rely on yourself.

You have no other choice but to learn and grow, and eventually? You will be more confident when you’ve done this enough times.

Ash grew her confidence as a copywriter by “sitting down and writing so many times you could no longer make a convincing argument that” she “wasn’t a writer. The same goes for you: do it enough times,” and you can be almost anything, “because success can’t outrun you anymore.” (The Middle Finger Project by Ash Ambirge, page 93 (Kindle edition))

I grew my confidence as a web designer by taking action, –messy action, at that– and learning from each experience. Instead of being scared to take this or that project, I started taking almost anything as long as I had a general skill set to do it and the confidence to navigate unfamiliar waters. –And yeah, I got into a sticky situation or two, but I handled it! And everything turned out fine.

–And that’s the part you need to latch onto trust that you can handle whatever situation that comes next. You don’t have to handle it perfectly, or even well, but you do have to trust that you CAN because “handling it” is how you build experience, expertise, and eventually confidence.

The sticky situation.

Once I took on a project to help a company migrate from one CRM to another because I love systems and processes and organizing in general, but also because she needed my help and I’d been a long-time user of the CRM she wanted to move to. Otherwise? I had absolutely NO idea what I was doing because I was a web and graphic designer, not a… well whatever that title should be.

As I began to go through the company’s client list, see the automated emails that had been set up, dig into their project management app to see the processes and timelines, and start moving things over,… I felt staggeringly overwhelmed to the point that I became terrified.

Suddenly, I KNEW. The kind of awful capital “T” truth realization that you don’t want to face. The “holy sh*t, I have made a HUGE mistake and I’m going to look like a fool when I inevitably have to own up to it.”

This wasn’t me being scared or feeling like a fraud, it was me accepting a work order to build a model rocket, that turned out to be a need to build a functioning rocket ship.

I was completely out of my depth here; I knew my limit, and this was it.

I knew I couldn’t make the software do what she wanted it to do and I also knew without a doubt that the new CRM wasn’t the answer to her problem, which was the crux of the problem. She wanted and chose that new CRM specifically, and then she hired me to move her content to this new CRM.

After taking a deep look, I now fully understood that for her business model & her needs, this software was absolutely the wrong choice.

I had 2 options:

  1. I could do what she wanted and migrate everything over (and I did try this, first) or

  2. I could have an honest conversation with this client and tell her to do what was best for her company, even if it meant admitting failure, in a way.

It made me so nervous I was hyperventilating. I was crying hysterically. It made me sick to my stomach, hands-shaking, voice-breaking, couldn’t-breathe, –scared to death.

BUT I knew I had to tell her the truth, so I drank a White Claw (true story!) and called her on the phone. Luckily for me at the time, we lived in such a rural area that our internet provider did not have the kind of big monthly data caps that would’ve allowed me to do video calls, so a Zoom call was never in the cards, and thank hell for that.

I told her the new CRM wasn’t the right solution to fix the problems she was having with the old one. I also told her that my expert opinion, such as it was, was that I was not the person she needed to do this job. That I couldn’t make the software do what she needed because it didn’t have the capabilities she needed, and since I didn’t know of any other software that could (which I also had personal expertise with) that she had to find someone else to get it done.

Then there was silence for a moment.

I was scared sh*tless! What will she say? Will she berate me? Yell at me? Will she leave me a bad review? Will she tell everyone I’m a fraud? Will she want her money back? Will she sue me? OMG, what if she does ALL of those things?!

Instead, she apologized to me for not providing more details upfront that would’ve helped me realize the scope was too large for me, for the new CRM, and for my level of expertise. She said she was sad not to continue working with me, but she appreciated me telling her the truth, knowing it was hard for me to do so.

I had offered her a full refund because I’d been so scared she’d be livid, but she turned it down saying she knew I’d spent hours on it so far and had seen results of the time worked, and wouldn’t accept a refund.

She’s good people.

It’s okay not to be ready (and do it anyway).

That experience taught me a HUGE lesson. It’s okay not to be perfect. It’s okay not to be good at everything. It’s okay not to know everything. It’s okay to fail.

We don’t get experience, and we don’t grow, from only walking into situations where we know everything and by playing small. We get experience, confidence, and expertise when we walk into hardships and we learn from them. When we play big. 

As a beginner, no one expects you to be perfect and know everything there is to know about anything. If you did, you wouldn’t be a beginner now, would you?

Stop focusing on what you DON’T have, and start focusing on what you want. Take action on that, and I promise you, you WILL make progress.

If you walked 1 mile in the same direction every day, eventually you’d reach the ocean, no matter where you started.

Staying small, avoiding all risks, and being afraid to take action will keep you exactly where you are. And you will miss out on your dream life in the process.

I know this because it’s what I did for the first 5 years of my business.

It wasn’t until I took a big risk by deciding not to go back to that 9-5 even when they were ready for me again (and they did want me to come back), that forced me to radically rely on myself. That’s when big changes started to happen.

I changed my business name from a stuffy ‘studio’ sounding design business name to an unorthodox, light-hearted, confident “Launch the Damn Thing!”

Then my audience changed, my written voice naturally changed, my confidence changed, and my approach to business changed. My inquiries changed too, and they began coming in more frequently.

People responded to my portrayal of confidence, even when I didn’t feel it yet. Eventually, when you show up every day and take action on ‘the thing’ (whatever it is), confidence can’t outrun you anymore! And neither can success.

Now I’m booked out for the next 3 months solid, and I’m still getting inquiries! 

Now I’ve made more this year than I ever had at my 9-5, and I’ve had time-freedom, and location-freedom while I did it.  

Now I’m happy doing work that fulfills me and makes an impact.

Now I wake up smiling and excited to work.

Now I’m proud of what I do and the business I’ve built from absolutely nothing even though I had no idea what I was doing most of the time.


Now? I love Mondays. ❤️

I’m not an anomaly.

If I can do this with a 15GB maximum monthly data cap on our internet usage back when I first got started, a college education on art (not business) and no clue how to start or run a business, limited time outside of work, and maybe a hundred other things going “against” me, –then you can too.

You CAN wake up every day and choose your schedule, choose your clients, choose your projects. You CAN choose your vacation time, your salary, your profit, and your location. You CAN choose how you show up, and how you don’t; which audience you show up for, and who you don’t. You CAN choose how often you work and how often you play. You CAN take the afternoon off to nap, or only work nights if that’s your thing.

Whatever it is that you want your work to look like, you can make it happen!

But you can’t play small, and you have to take the first step, despite.

Your biggest fan,

Katelyn

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Dear web designer…playing it safe is keeping you from your dream life & business by Katelyn Dekle