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Oh Sierra


5 Things to Know Before Growing Your Creative Agency

We help creative leaders harness the potent power of community (online and IRL) with content strategy, education, and events.








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Back in 2017, we started Oh Sierra as a catch-all freelance creative studio, saying yes to any project that came knocking.

Copy? Sure. Social media? Mhmm. Photography? Let’s try it.

…Sound familiar?

It took YEARS to get clear on what we really loved, excelled at, and where we could best serve our clients. Years of ups, downs, mistakes, and lessons.


Once we finally felt comfortable in our capabilities as a studio of two, we hit the tipping point: stay small and cozy, or seek something bigger.

So, we started hiring.

First an Ops Manager, then a designer, then a strategist… We grew our humble husband-wife duo to an agency of 6 talented creatives, expanded our offerings, raised our rates, and chased our big agency dream at full speed. We fostered a community of incredible, inspiring clients. We hit record high monthly revenue numbers.

It worked… For a while.

Then, like clockwork, came the lessons.

The digital entrepreneurship culture has us constantly hearing promises to the tune of SCALE — but what rarely gets discussed is how your life looks on the other side.

The reason we chose to *grow* was to create more space to *live* but turns out, that isn’t how it works.

It was a wakeup call that more isn’t always the solution.

Just like saying “yes” to every obscure creative ask that came our way didn’t get us any closer to our dreams in our early days, making hasty strides towards growth didn’t magically grant us access to our ideal lifestyle, either.

If you’re finding this post with aspirations to grow your agency beyond a solo studio, there are 5 lessons that we wished someone had told us before we started growing Oh Sierra.

We share these lessons with the complete understanding that everyone’s path looks different, but in hopes of ushering you with some preparedness towards a more inspired, aligned next chapter of building your creative business – and we’re getting there, too.

Scaling is a Myth

No hate to that “3 Steps to Scale Your Design Biz!” listicle that you saved on Pinterest, but your current business model – with its existing systems, financial ratios, profit margins – may *not* be scaleable. That doesn’t mean growth isn’t possible, but in our experience, it’s much more realistic to look at your next phase as a new iteration of your business, rather than just a blown-up version of your existing one. That might mean overhauling the whole damn thing, from systems, to rates, and beyond. A creative agency and a freelance studio don’t operate the same way, so instead of thinking, “how can I sustain MORE of what I already have?” start asking yourself, “what do I need to REBUILD to sustain where I want to go from here?” 

The Systems Aren’t Cheap

Software, as a line item. Right before we started expanding our team we had saved countless productivity apps and set out to research all of them to decide which one was right for us. Turns out, none of them – and thus, all of them. And HELL YES, it’s been worth it – but the number of systems we had to suddenly juggle came as a shock to our brains and our bank account, not to mention the additional support we hired from experts to help us learn the systems more quickly so that we could adequately lead our team. Keep an eye out for hidden charges for extra team members, storage, and don’t rush to implement a new app until you’re SURE the ones you’re already using couldn’t do the same job. Perform regular audits to avoid under-using apps that may have released new features, and don’t be afraid to release a system that doesn’t serve you.

Teamwork is A Two Way Street

Obviously, right? But if the first time you’ve led a group of people happens within your own business, it’s a SHIFT to realize that it’s not just your orbit, anymore. Just as new personalities on your team will impact your work/life balance, joy, and creativity, YOUR energy is also becoming a part of someone else’s day. This means putting in effort to listen and learn from them, ask for what they need, and show up in a way that makes them feel confident and inspired even, and maybe especially, when you don’t feel like it. I’d like to defer to Brene Brown for the remainder of this lesson.

Leadership Hours Are Billable

With business growth, you won’t always be the one handling the deliverables – but there’s still a value for your time to manage, delegate, direct, communicate… the list goes ONNNN. We highly recommend starting to use a time-tracking app like Toggl as you step into a leadership role within your business. I tried this for a few weeks and was astonished at how many hours of my day were dedicated to managing project-specific tasks that weren’t accounted for in the client’s proposal.

With Higher Income Comes Greater Responsibility

…And that’s an understatement. While your earnings may grow, the number of things you need to manage will multiply exponentially. We have always been advocates for seasons of push + seasons of rest – until we rode the growth push so hard that rest became unattainable. The absolute most impactful lesson we can leave with you is to outline the life you want to lead before you build a business that could hold you back from living it.

If you’re feeling stuck in your creative business and lacking the support you need to make the leaps you know, deep down, you’re ready for, we’d love to teach you how to sustainably scale your agency in a way that supports your ideal life. Learn more about our mentorship community for creative entrepreneurs here.


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About The Appleyards

We Are Passionate Community Cultivators, Partners in Life and Business, And Firm Believers That Work Should Feel Like Play.

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