Insights / Business

The Highs and Lows of Running a Digital Design Agency: An Inside Look at Southleft

Navigating the terrain of agency ownership isn't for the faint of heart. Explore the highs and lows, innovations and setbacks, that define Southleft’s story.
12 min read
A colorful abstract painting depicting high and low emotions
A colorful abstract painting depicting high and low emotions (Source: Midjourney)

Starting a digital design and development agency is a journey filled with loads of excitement and unpredictability. When you’re at the helm, as I am at Southleft, you experience a gamut of emotions that come with achieving success and facing challenges. In this candid narrative, I’ll take you through the highs and lows of running Southleft. From achieving remarkable growth to navigating potholes in the road, I’ll share my thoughts and experiences from my perspective on what it’s really like to run a digital design agency.

The Lows:

I’m going to start with the “lows” here in an attempt to end on a high note. Note that these lows are likely to be fairly common amongst agency owners and I’m aware that countless articles and workshops exist to remedy these challenges, but, in my opinion, they’re inevitably unavoidable.

General Challenges

The anxiety of the sales pipeline drying up, the unpredictability of the economic landscape, navigating the sales and marketing side of things, it all adds up. The worst parts are the ones that feel like they’re completely out of your control.

This year (2023) has been especially difficult and unpredictable. It just seemed like there was nothing we could rely on data-wise to predict or forecast how this year was going to shape up. Nothing seemed to add up. As a result, it was the first time in 10 years that we had to lay off team members. A gut-wrenching move I felt woefully unprepared for.


It’s bound to happen at some point over a long span of time. Not all relationships are made in heaven. Many require a substantial amount of work on both ends to maintain a trustworthy and respectable connection. This goes for all typical parties interacted with: the team, clients, and agency collaborations. Despite my best efforts to be candid, we’ve had partnerships go sour and faced internal struggles that led to uncomfortable confrontations. As someone who despises conflict, these instances shake me to the core. All I can do is continue to fall back on my morals to convince myself that, in that moment, I did what I thought was the right thing to do for the business and the team. And hopefully, I can use these uncomfortable moments to learn from in the future.


We’ve also had our fair share of train-wreck projects, the kind that set us back so far we end up funding them. These are hard lessons that need to be learned from. I’ve been guilty of letting too many of these types of projects slip by because the pipeline was full and the next project would help fill the empty bucket the previous project left. There are moments where I believe it’s in good favor to the client to give a little where appropriate as a sign of gratitude, but the line between graciously donating resource hours as a nicety and being taken advantage of can quickly get blurred.

Over the course of time we’ve tightened these reins. Where in the past I feared that if we didn’t make the client happy, even at the expense of our revenue, then we’re burning a bridge and that client would be left with a bad taste in their mouth when thinking of any future work with us. And since our main source of business is via referrals, I feared those clients would spread word that Southleft is a “difficult” agency to work with. We’ve since gotten over those fears and come to learn that clients (the good ones) respect our boundaries and sometimes need to be told/guided on what can and cannot fit into scope.

Stress and Burnout

Burnouts and high-stress periods have occasionally plagued the team. As much as we try to protect against it, it finds a way to seep in from time to time. The difficult part to identify and gauge is burnout from an individual team’s perspective. Not all burnout is created equally and multiple factors play into what can cause burnout. Also, people’s tolerance level to the limits of burnout differ from one another. It’s a three-dimensional moving target. But what we do know is, when it hits, the mental toll it takes is palpable.

In these times, I insist on the team taking days off to recharge. The hopes are with some time away from work screens, this will help with rest to recharge their batteries and help clear the mental muck clogging up cognitive functioning. Occasionally, for “all hands on deck” type of situations, monetary bonuses serve as an acknowledgment for their extraordinary efforts. These types of rewards typically coincide with some time off in an attempt to try and restore some balance to work and home life.


At times, the weight of the pressure I put on myself makes me question the path I’ve taken with Southleft. Admittedly, it gets very lonely in my position. I don’t have any partners or investors to answer to or reach out to for advice. I spent an abnormal amount of time thinking about projects, the team, and overall business strategy. I stress over the project pipeline when it’s low and I stress over the project pipeline with is full stressing over how to keep it that way. I worry about the team’s job happiness and fulfillment. Even when everything is coasting and there’s nothing to stress or worry about, I worry about why I don’t have anything to worry about thinking I’m missing something I should be doing to further the business.

Yet, even after all that, I circle back to the positives: the incredible people I’m surrounded by, both within Southleft and the wonderful people we have the opportunity to work with; the processes and decisions that got us here to a successful state; the audience we’re able to design and build products for; the whole front-end designs/development community; and this list could go on… I find solace and motivation in these things and it keeps me focused not on how hard the next obstacle is, but questioning with positive momentum, “how hard can it be?”

The Highs:

Initial Success

It’s a surreal experience, looking back at where I started with Southleft. In the beginning, it was just me, freelancing and dreaming of something more. I diddled in freelance here and there, but all while having the support of a full-time job. It was in 2013 when I left my position as Director of Front-End Development at Martha Stewart Living Omnimedia (MSLO) to move back to New Orleans, LA and officially start Southleft, LLC.

Fast forward 11 years – now, we’re a legit contender in the front-end design and development space, with multiple Fortune 500 companies in our client list and countless other projects and clients to be proud of. The breadth of projects we’ve tackled is staggering; from the tiniest brochure websites to colossal web applications that reach millions of users. That transformation fills me with a deep sense of pride that’s hard to put into words. I have a lot of folks to thank for this growth, but mostly my fellow colleagues at MSLO, for without their friendship and support, I never would have had the bravery and blind ambition to venture into this journey.

Team Growth

Then there’s the team. Ah, the team! Watching them grow both in overall size and skillsets has been a rollercoaster of emotions. From the early days of hiring our first developer to now managing a full-fledged talented unit, it’s been a wild ride. Those “ah-ha!” moments when they finally get it? Priceless.

We hired our first team member in 2016 and that was a huge decision (and she’s still with us to this day!). This was the “official” moment that took Southleft from just freelancing TJ to a full fledged “official” agency. Over the years, we’ve adopted some hiring best practices and have steadily grown the time to the 20-ish team members we are today.

It’s a reassuring feeling seeing the size of the team grow because that usually symbolizes project/pipeline growth, but timing new hires, though, remains an art form. It’s like walking on a tightrope between project demands and available talent in the industry. We’re still navigating the delicate art of when to hire, but feeling more and more confident with each round.

Client Satisfaction

We’re more than just a business; we’re a collection of people who believe in doing good. Often, we’ll go above and beyond for a client, even if it hits our bottom line. A lot of times it just ends up being an out of pocket expense for us, but morally it felt like the right thing to do. I understand businesses shouldn’t necessarily be based on morals, but I’m a firm believe that if you do good things, good things will be done to you.

The payoffs? Beyond monetary gains. We’ve forged friendships, received phenomenal referrals, and added more layers to our project phases—all because we decided to go that extra mile. The lesson learned is sometimes it takes a little giving without the expectation of any immediate return. Giving selflessly, but within means. It feels good and could have a potential added benefit down the line.


Being in this ever-evolving tech landscape is like being a kid in a candy store. New technologies sprout up daily, and our team is ever-eager to incorporate them into our projects. Most projects we start on we try to implement something new into them. Maybe a new front-end framework, or build system. Or maybe some project management software, etc… We’ve been working with native web components, an area not as explored as other front-end tools like React or Angular and it’s an exciting moment to be working with technology that’s so cutting-edge that it’s rapidly evolving as we’re rolling it out to projects. It’s this pioneering spirit that keeps the work thrilling.


The lifeblood of Southleft lies in its partnerships. I wrote an article more on partnerships here. We sincerely appreciate our partners and do our bet be an honorable and accountable partner to whomever chooses to work with us. Partnerships typically work best when we’re paired up with one or a few other agencies/contractors that offer complementary services to ours. We’re the Avengers of the digital world, each partner bringing unique superpowers to the table. When it clicks, it’s magic. We’re all committed pros, going beyond the money and vibing on a level that’s rare to find.

Personal Insights:

Leadership Lessons

I don’t claim to be a leader, but I often have to assume the role of a leader. While I don’t have any famous quotes or words of affirmation memorized from the dozens of business strategy books I should’ve been reading, these are a couple of lessons I’ve learned over the years:

  • Lead with your morals and trust those morals. Really take time to discern what a right decision would be taking all parties and time into the equation.
  • Have faith in your team. It may not always work out the way you expect it to work out, but the results will only help to make the next leap of faith a more successful one.
  • Don’t get caught up in the details. If you’re leading a team, show them the goal and the milestones that need to be achieved along the way, don’t blaze the trail for them. Provide helpful resources, don’t give them the answers.
  • Understand and really hone in on each team member’s method of learning. Some are highly successful when they’re thrown into a codebase they’re not familiar with and just figuring it out. Some are better when they’re paired with another knowledgeable resource to work with them. Some are better when studying up by reading books and watching educational videos. Figure out what works best for them and apply support.
  • Micromanaging is OK. If a team member could use some upskilling but lacks drive, it’s ok to give them personal attention to help boost motivation.

Work-Life Balance

Work-life balance is what you make of it. It’s a tricky concept, but I’ve managed to find a rhythm that works for me. I’m fortunate enough to have a loving wife who’s able to homeschool our three children. Southleft is fully remote and has been since day one, so the whole team, including myself, has the ability to work from virtually anywhere (as long as there’s a decent wifi connection). We have flexible hours so if I have day time appointments/errands, I can take them and put in a few hours in the evenings. I reflect on this setup often when I think about any negative thoughts or doubts about the decisions I’ve made along the way.

The Future

While the journey of Southleft has been anything but linear, I wouldn’t change a thing. Even the lows have taught us something valuable. They’ve forced us to innovate, to build stronger relationships, and to get a little more creative with our problem-solving. We’re still figuring things out as we go, but the one constant is that we’re always moving forward. And for a business, especially in the digital space, stagnation is the real enemy.

In Closing

I started Southleft to do what I love and to work with people I respect. The lows can be low, but the highs/benefits far outweigh them. When you work with great people, both on your team and in your partnerships, the journey is the destination. And what a ride it’s been.

Thank you for taking the time to read my story. Until the next chapter unfolds…