How I went from a corporate dropout to a multi-six-figure social media marketing agency owner.

hello digital social media marketing cedar rapids iowa

There is nothing like the despair of hitting rock bottom (or at least what feels like rock bottom). I was in the thick of it in 2018 when I realized my corporate marketing career was draining my life out of me.

This blog post isn’t meant to be a “wow, look at me!” story. Instead, I want to provide some realness to what it actually takes to build a business into a success and then, when you “make it,” what that actually means. Hint: the grass isn’t always greener.

If you resonate with any piece of this story, leave a comment and let’s connect.

Year 1: Leaving my corporate job to become a social media marketing freelancer.

Have you ever woken up one day and decided, hey, this sounds like a good day to make a rash decision to uproot my entire life and all of the securities I have built?

Because I have! The decision to leave my corporate social media marketing job was not planned in advance or thoroughly thought through. The enormity of this decision was made even more significant by the fact that I had a 2-year-old daughter at the time and very little in my savings account. Why my husband supported this decision so effortlessly still has me questioning his sanity, but spoiler alert: everything worked out.

During the last few months of my corporate job, I dabbled in social media marketing freelancing as a side gig using a website called Upwork. When I quit, it became the means to my financial well-being. It had to work.

Upwork allowed me to list myself as an available contractor for businesses that needed to outsource social media marketing projects. My strategy for getting work without much freelance experience was to list my services for super inexpensive prices.

Even though I was underpaid and taken advantage of in this new social media marketing freelance role, this period of struggle taught me some essential lessons that I still carry with me today.

Lesson 1: Sometimes, you have to value gaining experiences above the value of income, but this won’t (and shouldn’t) always be the case. Thinking of this as an investment in yourself is a great way to frame it because, realistically, you can’t charge more if you don’t have the experience to prove your worth.

Lesson 2: Creating boundaries for yourself in business is essential for your mental health. Not every opportunity is a “yes”. Identify red flags, and have the mindset that turning down unaligned opportunities doesn’t take away income. Instead, it keeps your time available for opportunities that do align.

Lesson 3: Hustle culture tells you that you need to always be working and reaching for opportunities. And that’s somewhat true. You really do get out of it what you put into it. So, if you want to grow faster, you need to spend time learning, doing, creating, and communicating.

Year 2-3.5: Turning my freelancing gig into a social media marketing agency

There’s something to be said about hard work, consistency, and not quitting when things get hard. The secret to life is believing in your abilities, working to improve, and taking mishaps as lessons that you can learn from; you will always succeed.

For me, it took exactly two months to go from a single freelancer to having more work offered to me than I, as one person, could handle. I feel grateful that my brain doesn’t process risk as a bad thing because I took this situation as an opportunity to hire my first contractor, Emily, to help me take on the work that I couldn’t do alone.

Emily and I worked together to continue building and growing our client roster. Eventually, I got an official LLC and turned my sole proprietorship into a functioning agency. That’s when Hello Digital 1.0 was born.

The funny thing about Hello Digital 1.0 (and, to be honest, with every new step of owning a business) is that I had no clue what I was doing. It was a constant research, try-and-test, and figure-it-out-as-you-go situation.

Here are the main lessons from building a social media marketing agency:

Lesson 1: Every single person starts from square one, and there is no way to cheat your way into knowing everything. You have to take it one step at a time and learn by doing. The more you know, the more you know. This has helped me understand everything from how to run a business to how to price my services to how to invest in hiring new people.

Lesson 2: When you have people counting on you for income (employees or contractors), it can add a new element of stress and pressure. This, in my opinion, is good, but it can also allow you to let your boundaries slip if you’re not careful. Strong communication with your team is really important in making sure you’re on the same page with opportunities to take on or not take on.

Year 3.5-4: Merging my agency with a local social media marketing agency competitor

I really try to live a life without regrets and to see every situation as a learning opportunity, but this one really challenges that mindset for me.

So much so that I’m going to leave out most of the details of this era of my business. This merge lasted less than a year and completely wrecked my mental health.

Let’s jump to the lessons I took from the merge.

Lesson 1: Most of the time, a too-good-to-be-true opportunity is actually too good to be true.

Lesson 2: The business you have poured your heart and soul into is yours to own, and every decision you make that affects its livelihood should be taken seriously and given great thought.

Lesson 3: People take advantage of you when you’re doing well.

Lesson 4: Trust your gut, and don’t wait to act on it. If you find yourself in a bad situation, don’t try to convince yourself that you can make it better by changing XYZ. Sometimes, sticky situations come to you to show you that they’re not serving you, and it’s best to listen to that.

Year 4: The comeback.

I consider the second half of year 3 to be my career low. This means that anything that comes after is really good because my motivation is higher than ever. Right!?

Taking back my business as my own really reminded me why I went the entrepreneur route in the first place. My goal with owning my own business is and always has been to be able to live a life of financial freedom on my own terms and on my own time. Entrepreneurship is the only thing that allows for that lifestyle, and the only thing that allows entrepreneurs to find big success is through investment and risk.

This entire year I spent putting detailed focus on the things that I knew would make a difference in my business.

  • My content turned into a humanized and authentic focus, caring less about judgment. I realized that I’m not for everyone, and the more I can show up as who I am and how I work, the easier it’ll be to find more aligned clients.
  • I implemented simple but efficient processes to help accelerate growth
  • I felt less nervous about hiring people and adding on to my team, because I had already proven to myself that without a good team, my business wouldn’t grow.
  • I said more “no’s” to opportunities than ever before, and each no led to a better yes.

The comeback year lessons are my favorites. Take note!

Lesson 1: The idea that there is a right way and a wrong way to do anything is completely bogus. The only right way is the one that works for you. Don’t feel the pressure to “have” to do things a certain way because that’s what somebody told you. To figure out YOUR way, look at your data, your goals, and your desires.

Lesson 2: The quicker you realize that social media marketing is about community and building brand awareness, which is an essential step in acquiring a new client, the quicker you’ll grow. But you can’t stop at social media; you have to have a way to funnel your audience and nurture them. Invest in a good strategy.

Lesson 3: It’s normal to feel inadequate even when things are going well. It’s normal to go through phases of high motivation and burnout. If you can follow your body’s lead on those phases and give it what it needs; whether that’s periods of doing “less” or “more”, you’ll realize that your overall happiness and success flows faster and with greater ease.

Year 5: Hello Digital 2.0

As I’m writing this, I’m in month 7 in year 5 and this year has been undoubtedly the best year yet.

I have taken a step back from doing the client work, which now is 90% taken care of by a team that I have full and complete trust in. Now, I get to spend my time mentoring other social media marketing professionals, creating courses and resources, coaching entrepreneurs, working on my business and strategizing new ways to market, and looking at data.

At the beginning of this year, Hello Digital had hit $300k in annual revenue, which I never thought I’d see.

Some weeks I work 60 hours (when I feel like it), and other weeks I work 5 hours.

I have made the leap to invest in outsourcing SEO, https://hellodigitalmarketing.co/wp-content/uploads/2024/10/kaboompics_young-entrepreneur-dressed-in-brown-suit-desk-laptop-computer-27949-scaled-1.jpgistrative tasks, and content repurposing for Hello Digital to a full-time employee which frees up 40 hours per week of my time and even though it’s an expensive investment, it’s been worth every penny.

Lessons from the growth goal crushing year:

Lesson 1: Investing is the ONLY way you’ll be able to grow past a certain level. You can’t do everything yourself; there isn’t enough time in the day. Don’t be scared of it. Instead, when you see a need to invest, whether it’s because you don’t have the time or the knowledge or if you want to gain faster results, decide on a way to measure success and return on investment. It doesn’t always have to equal dollars.

Lesson 2: Rome wasn’t built in a day, and your business won’t be either. When you see somebody saying they made six figures in their first year, first five years, or even ten: it doesn’t mean that it is the new expectation. As with everything, the more time you spend, the more money you invest, and the more risk you take – the faster you’ll grow.

Lesson 3: You can learn so much by seeing what other people are doing, but paying attention to your competition isn’t the best way to understand your market. It’s always better to look inward than outward, and focus on your value and your identity to drive your decisions.

What’s next?

I’m going to start investing in advertising.

I’m going to build a brick-and-mortar location to better serve local clients in Cedar Rapids, Iowa.

I am going to empower my current team to manage the agency side of my business. At the same time, I become more involved in creating mentorship and opportunities for budding social media freelancers.

The best thing about entrepreneurship is that you have all of the control of your future. If you’re willing to invest in yourself, stay patient and persistent, and follow your heart tugs, you can achieve any level of success.

With more success comes more challenges. But with more experience comes a better understanding of how to deal with the challenges in an attainable way.

Are you looking to take your business to the next level? I would love to be by your side. Let’s connect.

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