Our Top 9 Lessons Learned From 9 Years in Small Business.

“I can’t believe it’s been 9 years.”...“I’m proud of us for being in business for 9 years.” 

And Andrea (in perfect Andrea fashion) quickly followed up those sentimental texts with a GIF of Dawson’s Creek’s James Van Der Beek crying his eyes out.

But really, nine years, y’all! That is 3,285 days since we officially became business partners. Running a small business is no joke. Staying in business past the 5 year mark is a feat that only about 50% of small businesses achieve. We can honestly say that the last nine years have been full of some of our greatest challenges and sweetest blessings.

As our life seasons have changed (hello kids) our business has changed with us. We remember well the “boot-strapping” days of beginning our company when there was literally enough money in the business account to pay sales tax. We’ve run a six-figure business and also a business that has “floated” through seasons of less while having babies and chasing toddlers.

As we both reflect on the past 9 years, we can, without a doubt, identify some lessons and choices we made that helped us to, for lack of a better word, not fail. Honestly, the list is much longer than this, but as sort of a tribute to our nine years, we are sharing 9 business lessons that have helped us create work that is working for our life season. Our hope is that if you are starting out in the small business world that these lessons would help direct your next steps. We know it isn’t always easy beginning, but taking those first steps really can lead to incredible opportunities. 

  1. Start before you’re ready. 

    There is this old German proverb that we absolutely love. “Begin to weave and God will give you the thread.” 

    Whether it be a new endeavor inside your business, or taking the first step to just START your business, we have found time and again that the first step is usually the hardest. So, go fill out that DBA, or send that first reach out. Whatever it is, just begin!

  2. Aim for progress over perfection.
    We are both recovering perfectionists. We would venture to say that some of our greatest regrets in business are from being consumed with perfection in our art and business. It’s held us back at times from going after some of the goals we wanted to pursue. Having kids has allowed us (ahem, forced us) to loosen the grip on the reigns of perfect. Honestly, in this season there just isn’t time for perfect. And there is a lot of good to share with the world right now. If we waited for perfection in our school portrait program, or print shop set up, new brand release, etc. we’d still be waiting to launch.
    You’ve maybe heard it said, “If you aren’t embarrassed by the first version of your product (or service offering) you’ve launched too late.” We look back and cringe at some of our “firsts” in business. But, you know what...those firsts had to happen to get us to where we are now. There is always, say it with us, “ALWAYS”  going to be room for improvement in your business. Don’t wait for perfect, just start moving.

  3. Outsourcing is key to longevity. 
    There will come a point in any small business where you will need to start outsourcing. That can be an intimidating word for people. Of course when you outsource you’re going to have to spend money. But, we strongly encourage you to take a long hard look at your time. Is there a non-income generating task that is taking up a significant amount of time for you? Could you use that time to book more gigs or sell more products and pay someone else to do that task instead? For us outsourcing has looked different in different seasons of our business, but we’ve consistently outsourced bookkeeping and highly recommend you do the same if/when you can! 

    Other areas of outsourcing might be graphic design, album design if you’re a photographer, paying a virtual assistant to handle client communication, or bringing on an assistant to handle invoicing, scheduling, order preparation, etc.

  4. Pivoting is okay.
    When we started our business partnership as wedding photographers 9 years ago, we were going to be lifers in the wedding industry. We loved everything weddings. As we started families, and those families grew, our priorities changed. But, we had spent so much time building a wedding photography business we weren’t sure what to do next. At the end of the day, our work doesn’t define us...any of us. It’s what we do to support our families, to use our crafts, and to serve others. It really is okay to pivot, and change the way you serve people.

  5. Business growth isn’t always about more money.
    “Don't get so busy making a living that you forget to make a life.” - Dolly Parton

    Leave it to Dolly to call it like it is. We can become so growth focused that our work becomes our everything. There was this season about 5 years into our partnership that we were working a ton and on the verge of burnout. After doing a coaching call with a financial business coach we tweaked some things. 

    And you know what happened? 

    Our business grossed about the same amount of money the next year. 

    BUT, we worked about half as much. 

    For the first time in a long time we had margin.

    We’d say that’s a win.

    On the financial statements our business looked the same, stagnant if you will. But, the amount of time we were trading for money significantly decreased. Keep that in mind if you view success in dollar signs. It’s not always about more money. In fact, some of the best growth might come in different ways. 

  6. Email lists really do matter; yes, even for you! - ***This section includes a referral link!
    By far our biggest regret in our business is not using email marketing from the beginning. If you’re venturing into small business you’ve maybe heard “build your list” a time or two. But those same words may also sound completely foreign or overwhelming to you. 

    The problem with email marketing is that most people get overwhelmed at the design/implementation/list building, and daunting costs associated with building your list. But, now, thanks to Flodesk, there is a better way! 

    Do not, we’ll say it again, DO NOT sidestep the importance of an email list for your business. Even if you think you don’t need one, START building your list now. Our first marketing email sent to a very modest list of 20-ish past clients generated over $1000 in sales. OVER $1000 for a 10 minute email. What?!?

    Our biggest regret is that we started our email list 5 years into business. The thought of all the missed sales opportunities kind of makes us sick to our stomachs, but, you can’t go back right? Learn from our misstep here, and start building your list today! 

    Flodesk has made email marketing achievable for the small business owners! With drag and drop design customizations they set you up for success in communicating with your followers and subscribers. When you use code LOFTCREATIVE you will get 50% off their services for life. 

  7. Goals are necessary
    “The thing about goals is that living without them is a lot more fun, in the short run. It seems to me, though, that the people who get things done, who lead, who grow and who make an impact… those people have goals.” —Seth Godin

    It’s easy to have vision for an idea or a business, or where you want to be five years from now. But, nothing changes if nothing changes. Goals matter, they really, really do. Goals are where that vision for your work or life takes shape. Sometimes it can feel like your goals are too small (or too big) to write down. Write them down. Keep them in front of you. Committing them to paper really is half the battle. And, again, 9 years into working for ourselves we cannot stress this habit enough.

  8. Take a course or invest in a mentor session.
    This really is one of the best times to start a business. With the world at your fingertips via the internet you can literally learn about anything from your computer. We cannot stress this enough - learning from people a little bit ahead of you in business can save you thousands of dollars in mistakes. Taking a course of interest to you, or scheduling a mentor session can be like drawing the “Go straight to Boardwalk” card in Monopoly. If you are willing to dig in and do the work, this type of continuing education is a way to fast track yourself towards success.Our first investment in continuing education was $600. The next year was our business's first 6 figure year. We’d say that’s a pretty good ROI. ;)

  9. Network, network, network! 

    Networking is a vital part of running a small business. Most of the time you will not know the value of a connection until you’re months or even years into a friendship. Your first priority in networking should always be relationships. Don’t be focused on the sale, or the referral. Those will come with time if the connection is a good fit. Always put forth the effort to know and support other small businesses in your area. 


Welp, that’s it. There they are, nine of the most important lessons we’ve learned (sometimes the hard way) from running a small business. We’ve been celebrating nine years with grateful hearts. There’s a few more ways we are celebrating - if you see us in your inbox you know there’s a great print sale happening this week! Use the code HAPPY9TH for 50% off* all loose prints in the print shop this weekend only! *Framed prints not included in the sale.

We’ve also got a new free print up for grabs via this link, as a way to say “Yay, and thank you” to our followers, friends, clients, and fellow small business owners for supporting us, journeying with us, and being a part of helping us create work that we love!

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