DIY: The Entrepreneur’s #1 Enemy
If you’ve ever felt overwhelmed, trapped by an endless list of tasks, and stuck in the weeds, I’ve been there.
Spending hours on Wix trying to build your own website, or watching online courses on how to build your own logo are adding to that suffocating feeling of spinning your wheels. Freelancers can be a great, budget-friendly option to help, but often times add to the pain.
If left unchecked, getting stuck in trying to figure out how to do things can send you spiraling into a cycle of self-doubt and demolish forward momentum.
I know this because this is exactly where I was, at the point of no return, where I almost gave up all-together on my entrepreneurial dreams.
If you’re stuck spinning your wheels and not knowing how to execute, this is for you.
The Backstory:
I’ve always known I wanted to build my own business. Ever since I was probably 12 or 13, everything I pursued was an effort to chase this idea down. I was getting ready to graduate college, top of my class, with an economics degree. Although I was interested in the content, getting a job in this field, getting a 9–5, was as good as death for me. At this point, I had several “failed” businesses behind me, and nothing to show for all of my years of work and effort.
I was trying business idea after idea, everything from selling customized dog leashes, to drop shipping iPads, to network marketing. The problem was I was trying to do it all myself — I’d get an online course on how to build an ecommerce store, or how to run complicated Facebook ads, and I’d spend week after week learning and trying to bring my ideas to life. Since I’d dabbled in graphic design and art as a kid, I would spend weeks building the perfect logo and website. But I kept losing money, unable to make any sales or meaningful income, and I had nothing to show for all of this work.
I was desperate to prove to the world that I was capable of more, that I could be successful as an entrepreneur. To make things worse, I had no money, and was barely making rent between waiting tables and driving Uber. Meanwhile, all my college friends were having the time of their life, starting their careers and exploring the world.
The problem was I kept getting stuck in thinking I had to learn and be good at every aspect of building and running a business. I thought I was a fraud if I didn’t do the logo myself or if I couldn’t also write the copy and run ads that converted. I spent all my time and resources on the wrong things rather than on the growth of my business. As a I result, fear and uncertainty took over — I found myself putting on a brave face, always saying how well things were going, just to feel at odds with myself when I got home. This resulted in years of cycling in and out of depression, feeling worthless, and like I was destined to live a life of mediocrity — that I just wasn’t capable of doing something more with my life.
I’d racked up some credit card debt and was so tired of always having to grind month after month to make rent, and knew I had to make a decision. At the time, I was working in a low-level management position for a fitness company and started considering what that career path would look like. Self-doubt and anxiety ran rampant, as I was terrified that I was wasting years of what could be successful growth for my company. But I felt powerless, inferior, and resigned to following my current role as a career, even though I knew I’d look back on that in 10 years and regret it. Taking that route meant giving up on my dreams and throwing in the towel, living a timid, wasted life where I never even tried to reach my fullest potential. I was settling and I knew it.
Then, something happened that shifted my entire way of thinking and reignited the entrepreneurial spark…
Despite being in the middle of an unmotivated fog, something told me to grab Tim Ferriss’ The 4 Hour Workweek, which had been on my shelf for a couple years at this point, untouched. This was when I learned about the idea of hiring freelancers to help you design your logo, your website, and your ads!
It was now crystal clear to me that I needed to stop trying to design all the assets for my business myself, and that the ultra-successful entrepreneurs actually DON’T do this themselves! In fact, by hiring someone else, I could focus on the things I was actually good at and could focus on growing my business.
I also learned that the quality of the designs was so much better when I had an expert own the process, and I could overcome my own perfectionism that was holding me back for years.
As a result, I started moving forward with an idea I’d played around with early on in my entrepreneurial journey, but never knew how to bring it into existence.
My plan was to build a team to help not just me, but other overwhelmed and busy entrepreneurs bring their ideas to life with the websites, logos, and content needed to move forward. I started building the concept for my marketing agency. But I didn’t stop there — I learned all I could about hiring freelancers and how to leverage branding and great design to create the ultimate competitive advantage. Sooner than I expected, I got my first client!
But there was a big problem…
My first client needed several graphic flyers for his upcoming events. Right around this time, the entire southeastern United States was in a frenzy prepping for the largest hurricane on record, headed right to us in Florida. Nonetheless, I hired my first designer, sent him the instructions, and waited with excitement to see the finished product to turn over to my client. A week went by, still no flyers, and the client was checking in everyday to see where they were. I kept buying time. Finally, the morning after Hurricane Matthew had rolled over our city and taken the power and Wi-Fi with it, I got the email from my designer that he finished the flyers! Whew, we did it. I ran outside, full of anticipation, to the hot, muggy porch, trying to find an inkling of cell service to download the images. Nothing. After some time, they finally loaded!
As I scrolled down, my heart sank and I felt enormous pressure on my shoulders, as each flyer got worse and worse. They were terrible! Not a single good design. I’d already paid my designer and had nothing of value to send to my first client after 9 days of waiting. The business idea I thought would finally rip me from the grips of a lifetime of 9–5 was suddenly a nightmare.
The next 3 days were a frenzy of stress, anxiety, and hours of time spent on emails back and forth with my designer just to try to get one project right. I was finally able to deliver the flyers to the client.
There was no way this was scalable, if a couple of flyers were going to take us 12 days to complete. Things continued on like this for several months as I battled time constraints with freelancers, communication issues, trying to locate the right thread of emails in my inbox and keep up with the most updated files. With each new client came the fear that my freelancer wouldn’t understand the directions or be able to deliver quality work.
I wasted months trying to figure out the best way to sort through applications, interviewing, and hiring with “blind hope” that I could build a team of reliable and talented designers. To make it even worse, I was still trying to do nearly everything myself, handling all the day-to-day pieces of my business while trying to create and design content to publish. This was taking me away from truly being able to grow my business and bring in revenue.
To make things even worse, I was losing money (about $10,000 that year to be exact — which when you’re funding that with your day job, is a tough pill to swallow) because of bad hiring decisions or bad quality work.
I had a choice once again — give up on the thing I worked so hard to build and return to a day job or find a way to make it work.
I ended up getting so frustrated with all I’d been through that I decided to learn everything I could about systems, streamlining, and finding top talent designers. I wanted to create a system that would take only minutes to use and guarantee top-talented designers were at the ready so I could execute quickly in my business.
I chose to call it “Upperhand Creative”.
I thought if I could just create something that would make it possible for entrepreneurs like me to get out of their own way, and give them a significant competitive advantage over competitors with astonishing design, I’d be really happy.
After endless hours spent figuring it all out and money wasted trying to hire the right people that weren’t capable or ended up ghosting me in the middle of projects, I created Upperhand Creative.
I can now create an entire brand or business (website, logo, content, lead magnets) in less than 30 days and fewer than 2 hours of work for me, which used to take years.
Within a year, we’ve helped multiple entrepreneurs go from idea to execution, and build a powerhouse first impression, all while gaining some serious momentum in their businesses. We’ve helped them build a new level of confidence as we’ve added hours back to their schedules. We’ve built new apps, ecommerce stores, high converting creative, and so much more in a fraction of the time it used to take, saving entrepreneurs the pain and endless time-suck of having to interview, hire, and manage freelancers or figure it all out on their own. All of this was done without a huge budget or learning curve.
As for me, after creating Upperhand Creative, I was not only able to regain control of my self-worth and confidence, I’ve also been able to stop procrastinating and step out of depression and anxiety. I went from thinking I had no choice but to settle and take the easy route, to running 2 successful startups.
And in the end, all of this means I’m now able to help other entrepreneurs pursue their passion and carry out their dreams by building strong brands, without the crushing pressure of figuring it all out on their own and trying to find the right person or software to help.
