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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.

Freedom Fridays, vol. 9: why you should find a way to manage your self-doubt

Liam Carnahan of Inkwell Content Services

Liam Carnahan of Inkwell Content has been working in the content world for more than a decade. Starting out as a lowly writer on a content farm, he eventually grew to become the Director of Content at a major digital content marketing agency in Sydney. But in May 2019, he decided he’d had enough of his agency life and left his day job to run Inkwell Content Services. In addition, he also runs Invisible Ink Editing as he pursues his passion and talent for helping other writers improve their work.

What does freedom look like for you?

“Right now, freedom for me is centered around being “globally unchained.” I spent 10 years, before I started freelancing, handcuffed to various desks. Now that I’m a freelancer, I can go wherever I want, as long as there’s an internet connection. I’m kicking off my celebration of “locale freedom” in April with a trip through Asia.”

“…If you can find a way to manage your self-doubt, you’ll be on the path to freedom.”

Liam Carnahan

When did you realize freedom was important to you?

“If you want to go way back, I’d have to credit that to my parents, both of whom taught me the value of freedom by giving me plenty of it when I was younger. My father’s a minister and my mom’s a therapist… and I’m a gay atheist. Despite these circumstances, they always told me that I should be my true self through and through, and that’s the ultimate freedom—feeling comfortable in your own skin.

When it comes to working freedom, I’d have to say America taught me the value of freedom—but I’m not being as patriotic as I sound. Working in a world where you are limited to 8 days vacation and almost no paid sick leave really teaches you the value of freedom, because you don’t have it. When I moved abroad to Australia, where 20 days paid vacation each year is the legal minimum, my eyes really opened up to how restricted my freedom was back in the states.  “

What one piece of advice would you give to people that are in pursuit of their own freedom?

“You are worth it! A lot of people freeze up when transitioning to a less traditional working life, because it feels like an impossible and scary undertaking. Underneath this, there’s probably a whole heap of self doubt. You don’t think you’re good enough, or that you don’t deserve to live the life you’re dreaming of. But you do deserve that life. If you have a hard time believing that, start asking yourself why you think you don’t deserve it. Talk back to that little voice in your head saying you can’t/shouldn’t do it, and tell it to mind its own business. It will never go away completely, but if you can find a way to manage your self-doubt, you’ll be on the path to freedom.”

As leaders in their space, they are always learning – what have you changed your mind/perspective on?

“Email. Honestly, I thought email marketing was dead until very recently. I’m an email purist, so I very rarely subscribe to marketing newsletters/email lists. My inbox is sacred and for work-related emails only. I assumed most people were this way, but oh boy, I was super wrong about that. In fact, there are many, many people out there who love email lists and actually look forward to them in their inbox every day or week. I’m still coming around on my own subscription habits, but I now understand that building an email list is a very valuable practice, if you can get it right.”

Most influential book?

“Hmm, I know you’re probably looking for a self-help book, but I’m a fiction nerd, so I’m going to recommend the best book I read last year, which was The Power by Naomi Alderman. Not only will the book’s thrilling plot suck you in, it examines what power means in every sense in the world, and will make you rethink the current power structures that exist in our society. Go pick up a copy!” 

Freedom Fridays, vol. 8: why you should pursue your freedom relentlessly

Ally Lozano is no stranger to sacrificing freedom for career success, trading time for money as an over-worked attorney. But she’s relentlessly pursued her freedom and blazed her own trail, becoming a seven-figure law firm owner that now teaches others to run their firms like a business. Author of Be the CEO of Your Law Firm: Gain Control, Turn a Profit, and Reclaim your Life, host The Six Minute CEO Podcast, and business coach, Ally shares her thoughts on freedom.

What does freedom look like for you?

“Freedom means creating a life where I can spend my time only doing things I love. It means true control over my schedule, being able to travel the world, and pursuing all of my different passions.”

“Pursue your freedom relentlessly. The only way to do this is to release the need to be perfect and to live up to other people’s expectations.”

Ally Lozano

When did you realize freedom was important to you?

“I realized freedom was important to me when I completely burned out on the practice of law because of working in law firms and working for other people. I was a prisoner to doing things someone else’s way. I found those ways to be inefficient and archaic. I craved to redefine the practice of law on my own terms and to serve my clients in new and creative ways.”

What one piece of advice would you give to people that are in pursuit of their own freedom?

“Pursue your freedom relentlessly. The only way to do this is to release the need to be perfect and to live up to other people’s expectations. Once you decide you want to live freely, you are going to have to fight off your inner mean girl who tells you that you can’t do it. You must do it anyway. People will tell you that you are crazy for trying to break the mold. You must do it anyway. You only get one precious life. Embrace the fullness of who you are – free from boundaries, expectations, and others’ definitions of who you are.”

As leaders in their space, they are always learning – what have you changed your mind/perspective on?

“I used to think that marketing and sales were dirty and sleazy. I used to think that if you did great work, you would just automatically get more clients and that if you had to market then you were less of a lawyer somehow. I realized that I was so wrong. You do great work and people need to find it. If you don’t market, people can’t have their lives changed by your great work.”

Most influential book?

“Too many to name! I read 3-5 books a week that I have endless amounts of wisdom to pull form.  My most recent favorite is More Than Enough by Elaine Welteroth.” 

Freedom Fridays, vol. 7: why you should be flexible with the process

After feeling crushed by debt and overwhelmed with her finances, Maggie Gomez set out to learn all she could about how to gain control of that area of her life. It was a grind, but eventually she moved from just surviving to thriving and now wants to help others get there too. She quit her corporate job as a Financial Advisor, Stock Broker, and Certified Financial Planner to start Money with Maggie. She helps others learn how to get out of debt, save money, invest, and increase their income via her YouTube channel “Money with Maggie” and Instagram posts and stories. She believes that when you bring awareness and intention into your financial life, you can truly begin to thrive.

What does freedom look like for you?

“Freedom in my eyes is having the ability to choose how we spend our time and money.”

“…There is more than one path to your dream. [Know] your ultimate goals and [be] flexible as to how you reach them.”

Maggie Gomez

When did you realize freedom was important to you?

“I realized freedom was important after spending 8 years working in a cubicle setting. I felt like I had little control over the majority of my time and on top of that I didn’t make enough money to fulfill all of my goals. “

What one piece of advice would you give to people that are in pursuit of their own freedom?

“If fear is holding you back from pursuing something, play out the worst and best case scenario of what following that idea looks like. For me, worst case would be that my business never “takes off” I drain my bank account trying and then have to go back to the cubicle world. On the other hand if it works I could follow my passion, work for myself and make the money I want to make. The best case for me was definitely worth risking the worst case happening.”

As leaders in their space, they are always learning – what have you changed your mind/perspective on?

“I have learned that there is more than one path to your dream. If I try to pursue my dream one way and it’s not working out well, then I try another route. Knowing your ultimate goals and being flexible as to how you reach them has been an important lesson I’ve learned.”

Most influential book?

“The most influential book I have read is The Four Hour Work Week, by Timothy Ferris. He discusses an idea of taking “mini retirements” through life versus one giant retirement late in life. Also, the creative thinking shown to find ways to become more mobile in our jobs so we free up more of our time was incredible.” 

Freedom Fridays, vol. 6: why you should practice gratitude

Ashley Bennington, highly driven businesswoman, talks freedom.

Ashley Bennington is a highly driven and enthusiastic businesswoman with a history of personal success and a focus around creating a strong company culture that facilitates growth within an organization. She is a sales executive for a human capital management company, Paycom. Here, she partners with company executives to make a positive impact in the personal and professional lives of their employees. With a robust suite of products that includes payroll, time and labor management, talent acquisition, HR management and talent management, Paycom lowers labor costs, drives employee engagement and reduces compliance exposure. Ultimately, Ashley’s passion is directly growing the enterprise value of an organization. We asked her what freedom looks like.

What does freedom look like for you?

“For me, freedom used to represent financial freedom. I always wanted to know I had the ability to do what I wanted and could support myself financially in those decisions. “

“Work hard and be grateful for what you do have… if you see things as blessings and not burdens, you’ll always feel more free.”

Ashley Bennington

When did you realize freedom was important to you?

“Freedom has always been important to me. One of my first memories of a child was my dad and I sitting down and talking about the financial impact of receiving a college education. He taught me to work really hard so that I didn’t have to worry about repaying any debt once I finished school, and I was able to accomplish that for myself. “

What one piece of advice would you give to people that are in pursuit of their own freedom?

“Work hard and be grateful for what you do have. Success varies per person, but no matter if you think you’ve achieved it, or you’re still on the path to achieving success, you’re blessed with good things in your life. If you see things as blessings and not burdens, you’ll always feel more free.”

As leaders in their space, they are always learning – what have you changed your mind/perspective on?

“Quality of time. Time really is precious and I look at myself now as a 26 year old wishing I would have put less pressure on myself growing up. I thought I had to graduate college and be considered a tenure working professional right off the bat. Everyone’s journey is different, so enjoy where you’re at right now. ”

Most influential book?

“On the subject of quality of time…  Let’s Get Real or Let’s Not Play by Mahan Khalsa.  It’s good for anyone in business, I would highly recommend it.” 

Freedom Fridays, vol. 5: why you should make your own rules

Amalie Orrange, Orlando branding photographer and creative business owner, talks Freedom

Amalie Orrange is an Orlando personal branding photographer for joyful and driven female business owners that love big laughs and lots of color! She’s a Florida native, a wife of a firefighter who she’s known since elementary school, and a mom of two wildly creative teenagers. Just like us, she also loves dogs and has two of her own: Sophie, Chiweenie rescue pup, and Mattie, a Golden-Lab in the process of training to be a service dog. As if her love for dogs wasn’t enough, she shares our own obsession with Orangetheory Fitness as well! She is also an avid Cycle Bar fan and loves finding new fun activities to keep active and social. 
Besides being a photographer, she is also a creative business owner, a business coach and community advocate with a huge heart for helping others discover opportunities within their business, and building strong business skills to excel talents and strengths within their brand. She prides herself in providing a customized experience that gives her clients bright, joy-filled, true-to-life images that can be used in countless ways to up-level their business and brand. She wants to encourage and motivate other female entrepreneurs and makers to live out their dreams and to get their brand and business noticed and appreciated by their ideal clients! Working with creative business owners who have a BIG love for helping others with their services or products they have created lights her up inside! 

What does freedom look like for you?

“Freedom for me is being able to spend quality time with my family. Being able to take time off to enjoy family vacations, travel, and have date days with my hubby! “

Going along and doing what everyone else was doing… isn’t always going to work for you – blaze your own trail!

Amalie Orrange

When did you realize freedom was important to you?

“When I was working at my last job at Starbucks, I realized how important freedom was. I was working for a company that I loved for 8 years, but was growing increasingly tired of having to work on someone else’s schedule.  Being a mom of two kids under three, working at a job 30+ hours a week and then building my business for photography at night and in my free time…. I was exhausted. I realized I had to make the jump for more freedom with my time and schedule. It was a huge risk but SO worth it! “

What one piece of advice would you give to people that are in pursuit of their own freedom?

“Do not look at what others view as success or freedom, make it your own. Everyone has their own idea of what freedom is, be it financial or time; build your own freedom dream! Write down and speak your goals on a daily basis. “

As leaders in their space, they are always learning – what have you changed your mind/perspective on?

“I would have to say the biggest thing I have changed my mind on was that I needed to go the safe route in business.  I took a HUGE leap and shifted my business three years ago from photographing weddings and engagements to photographing branding sessions. I started doing a new type of photography that was pretty much unheard of at the time.  I saw a need for branding photography and styling with so many small business owners, makers, and entrepreneurs showing up in the online marketplace and realized that there was no one in town doing this type of work.  So I made my own path, my own rules, and set the standard. Going along and doing what everyone else was doing or has had success in isn’t always going to work for you – blaze your own trail!”

Most influential book?

“This is hard because I have a few. I would say my top two are Jab Jab Jab, Right Hook: How to Tell Your Story in a Noisy Social World by Gary Vaynerchuk and Love is the Killer App: How to Win Business and Influence Friends by Time Sanders. ”