Advice for New Business Owners

Bittersweet Design Boutique advice for new business owners. Story of failure.

When it comes to starting a business, having a brilliant idea is one small piece of the entrepreneurial pie. More and more people want a little taste of this so-called dream life as a small business owner, but there are a lot of steps that are required before you quit your 9-5.

We’ve learned most of these lessons the hard way, but here are a few things we wish we would have known a decade ago when we were young and clueless as to how to go about starting a business.


1. Failing Builds Character

The one thing successful entrepreneurs have in common has nothing to do with the time they wake up each morning or the number of books they read in a year…what’s more important than these things is the ability to fail, pick yourself back up, & try something new.

I’ve shared our journey to financial freedom before, but if you’re new to the blog, you might assume that our ventures were funded by one of our parents or that we had it all figured out from day one. This couldn’t be further from the truth!

Thomas started out in the restaurant industry as a dishwasher in his early twenties. His friend drove him to and from work every day until he saved up a few bucks to put a down payment on a car. He now had a job, a car, and a lot of debt.

I, on the other hand, was coasting along on a full ride in college when I had an epiphany. It was around 4:30 am, and I could barely keep my eyes open after waiting tables late into that evening. I was the only person sitting at a lonely booth in the student union restaurant called Crossroads (I couldn’t make this up if I tried). While staring crosseyed at a textbook for hours without absorbing an ounce of information, I thought to myself, “What the hell am I doing here?”

The next day (which was really just a few hours later, because it was the middle of the night), I met with my professors to tell them I was leaving. Right then and there, mid-semester with a 4.0 and 90-some-odd hours under my belt, I was doneskies. For good. My professors tried to talk me out of making such a hasty decision, but I’d already made up my mind.

To make a long story not as long, I dropped out of college, started dating Thomas, who had worked his way up from dishwasher to Front of the House Manager, and moved to Austin, TX, where I’d only visited once with a friend. From there, Thomas got promoted again to Assistant General Manager and eventually General Manager, while I was trying to figure out what in the world I’d just done with my life.

It was funny how quickly our roles had reversed. Thomas got his life back on track, and I was clueless as to where I was headed or why I hadn’t stuck with the plan that seemed solid for such a long time.

The faster you fail, the faster you are able to grow & evolve into something GREAT.

2. Trust Your Gut

When your stomach is upset, it throws your whole body off. The same can be said about intuition. When you sense something is off from the get-go, it’s probably true.

I always knew I wanted to be an artist. From the time I could talk, if someone asked me what I wanted to be when I grew up, I’d tell them I wanted to be an artist. Actually, I probably didn’t tell them anything and shot loving glares at them instead (yes, Griffin got this from me), but I’d tell my family members, “I want to be an artist when I grow up!”

By the time high school rolled around, I’d been talked out of doing anything creative, as “Art is a nice thing to keep as a hobby,” my brother told me (along with pretty much everyone else). My brother is a really smart guy whose words of wisdom have always carried a lot of weight in my book, so I was sold on the idea of going off to college to major in engineering, like he did.

This didn’t last long. I found my way back to the Art Department my sophomore year of college but still felt there was something to be desired. Cue the Crossroads incident. Right there, halfway through my fourth year of college, I called it quits.

I know a lot of you have done something similar, which is why I wanted to share this post. You are NOT alone in any of your failures - no matter how big or small they might be.

Images by Scissortail Stories

3. There Will Always be Detours

Once we got to Austin, I waited tables at a restaurant in the heart of downtown while working at a Section 8 apartment complex a few days a week. I applied at every design firm in town and heard crickets as a response. The one guy who was willing to meet with me (only out of the kindness of his wife’s heart, as she also worked for the company and obviously felt sorry for me), told me my work “didn’t make him cringe.”

A year or so later, I got a call from an art director who’d seen my portfolio and wanted to discuss a possible job opening at his design studio. I was ecstatic. It was just the job I’d always dreamed of, or so I thought…

Fast forward about six months, and I got talked into taking out a $10,000 loan to ‘secure my spot’ at this dreamy design gig. My first paycheck bounced after taking out a huge personal loan. Did I tell you that I was making $400 a month at this job? Oh yeah…so many red flags these Rose colored glasses refused to see.

When something looks too good to be true and smells too good to be true, it’s probably too good to be true. If only someone could hold up a ‘Caution’ sign when we need a little guidance…

If you’re wondering if this entire post is about doom & gloom, don’t worry. We’re about to get to the good stuff!

4. Do the Work

There was no silver platter & no Daddy Warbucks, so we were forced to figure this thing out on our own.

Since Thomas had a steady job, I continued working side gigs, which included a job I’d landed shooting weddings with a couple of local photographers. I ended up creating new branding materials for my new photographer friends in exchange for the confidence needed to start my own business. I did whatever was needed to get my foot in the door. I showed up to bridal shows, designed wedding albums, and tagged along to photo sessions in order to learn everything I could about the industry.

One thing became really clear - I wasn’t made to shoot weddings. Or be a photographer of any sort. As much as I love all things creative, I work best when there aren’t variables known as ‘people’ involved. Maybe it’s a designer thing. I was ready to design anything and everything I could get my hands on, though. What started off as a rebrand for my friends’ photo business quickly snowballed into dozens of real, live clients who were willing to pay me money to do the thing I loved the most.

You might be the complete opposite - if people are your jam, do something that involves face-to-face interactions on the daily. If you crave hustle & bustle, maybe your long commute and fancy-pants office is the perfect fit for you! Each of us is completely different from the next, so find what you love, and put in the work until it starts to pay off.

5. Fake It ‘Til You Make It

When clients called to speak to ‘the designer within the business,’ I’d try to make my voice sound really professional as I discussed the ins and outs of ‘our’ business. “Yes, we can definitely do that for you, wink wink.”

Whatever project they dreamed up, I’d deliver. If a bride wanted triple-layered wedding invitations printed on metallic paper, I’d run to Best Buy to purchase a laser printer (that I’d later take back) and pull an all-nighter with my X-Acto knife to get the project done. It wasn’t a very efficient way to run a business, but it paid the bills.

Soon enough, I decided it was time to break up with my $100 printer and beloved X-Acto. When I printed, trimmed, and assembled every piece by hand, the profit margin was huge, but what I wasn’t accounting for was the amount of time it took to design, print, and put everything together. Slowly, but surely, I found trusted vendors who did an amazing job at printing things like business cards and wedding stationery, and I raised my prices to offset the cost of using a professional printer. To this day, I still print all of my press products through Miller’s Lab, in case anyone is looking for a printer that has great quality products & incredible service.

If you can focus the majority of your time on doing the things you love while relying on a team of people to help you out with tasks that aren’t best suited for you, you will eliminate a lot of unwanted stress in your business.

6. Learn to pivot, when it’s needed

The best advice I can give you is to constantly grow & evolve. If you are afraid of change, your business will become static.

After outsourcing all of our printing, I realized I was still spending a significant amount of time doing things I wasn’t crazy about - like going to the post office every other day and re-working the countless revisions I’d allow clients to send over with each project.

I eventually got to the point where I realized that a lot of my clients wanted the same thing: beautiful pricing guides, magazine templates, and a website design to showcase their best work. In an attempt to bridge the gap between expensive, custom design projects and cheeseball templates, I started creating my first line of high-end wedding templates for photographers. It took years of building up a library of customizable templates before this idea really took off, but if I’m really passionate about something, I have an insane amount of patience.

My point is that if you believe in yourself and whatever idea it is that’s in your head, give yourself permission to unleash that creativity. As long as you’re not relying on your parents, your loan officer, or anyone else to get the job done and your bills paid, at the end of the day, I say GO FOR IT. You just might look back and wonder why the hell you didn’t make your move much earlier.