Three years ago this August, I quit my job. The 10th also marks my 30th birthday. It might come as no surprise, then, that I’ve started to do a little reflecting about that time.
At no point growing up did I ever expect be an entrepreneur. I didn’t even know I wanted to be one until I realized what I really wanted was creative freedom, and the ability to consistently create things with meaning and value.
To truly do those things with consistency, it required taking my own path – not following the one bosses had given me.
Fast forward three years later, and I’m now running what seems to be a successful content marketing agency, Siege Media. We’re creating content that tens of thousands of people view each day. Every month we’re putting out something slightly better than we had ever created.
In our first year, our posts mostly consisted of SEO gimmicks. Roundup posts. Orchestrated egobait. Entering our second year, we had slowly moved on to visual assets – still SEO gimmicks, but mostly good-looking ones. Infographics, data visualizations, and etc. We started thinking about creating content that not only generated links, but also ranked for keywords in isolation – driving brand awareness and massive client value.
In year three we’re pushing the envelope. We’re taking infographics and animating them, and when we’re not doing that, we’re improving the stereotype with high-end photography with staged lighting and an in-depth planning process. We’re going from roundup posts to complex interactives ranking #1 for keywords with almost 100,000 visitors per month. We’re creating content that helps people make complex decisions easier – and we’re making more of it every day.
It’s only year three. I can’t wait to see what our team will execute tomorrow.
Lessons From Three Years of Ups – And a Few Downs
Although it’s been an absolute thrill growing Siege to nine people, it hasn’t been without its stresses and lessons learned. I haven’t done this before. I didn’t train for it. I just did it. Naturally, that comes with some pain. But from that pain has come growth, and I wouldn’t change it for the world.
“No” Will Be the Most Important Word in Your Vocab
I come from a middle class childhood and am the sole, bootstrapped founder of Siege. With that reality comes the feeling that at any second everything could go – even if it can’t. What if something goes wrong? What will I do? Why does it feel we can either be 100 people or 0, and nowhere in between?
That fear also comes with a prescription of “yes” – a yes that will inherently break down everything you do. In year three, there’s no doubt that the biggest weakness in our current armor comes from what I’ve been unable to say no to. The wrong projects. The wrong clients. These things look shiny at first because they attract a paycheck – and help subside that fear temporarily, but inherently prevent us from making more efficient decisions down the road.
We won’t blow up tomorrow if we don’t say yes to that small project. Or that big one. It won’t happen. But it will always feel that way. I don’t know that that will 100% change tomorrow, but every day I understand another “yes” mistake that I’ve made, I feel a little closer.
Nine People is Where Everything Breaks Down
We’re now nine people, and now, every weakness in what I do is felt. I feel desperately lacking time. Like I need to work every weekend. And it comes from lack of delegation, lack of “no”. Lack of stepping back and thinking strategically.
Every company is likely different, depending on how the org chart looks, but somewhere around this level, I bet every new entrepreneur will start to understand the troubles. It’s the point where I start to ask myself questions like whether I should hire a dedicated project manager (that’s pretty much me). Or if I’m spending enough time helping our team grow personally. Or if I should hire a part time accountant. Or if we’re spending enough time thinking about business development.
And with those questions come overhead. And with overhead comes more complex business-running – complexity I did not sign up for.
It’s very possible to forsee the ninth person, or the 12th, and how to prepare for that growth. I didn’t. I want to stay small. And we’re still at the point where we can do that. But even at ten, there are decisions and structure that should be built in to make it a streamlined ten – and not an extremely inefficient one.
Client Work Can Be Its Own Boss
I realized at a given point that I did not want to be micromanaged any longer. I definitely could work in a non-founder environment again – but not in one that I was forced to do things I didn’t believe in.
At times, which also comes with the “yes”, client work becomes its own boss. Not always. It doesn’t have to be. We have amazing clients. But we’ve had bad ones too. And most of those bad ones had clear red flags that I took because of the fear. And they became the boss.
This environment became its own lack of fulfillment, and not something I enjoy. I’d fear opening emails in the morning, but I’d have to open the emails. I, or our team, would have to work long hours to achieve aims I had locked us into.
I want a work-life that makes me want to work long hours, but not be forced to.
How do you avoid this as an agency owner? By circumventing the fear and understanding another lead will come – if you know how the previous others had as well.
This is a paradox for an agency owner – I believe many of us are inherently faux entrepreneurs. We didn’t take real risk – we were generating lots of service leads and then quit our job. Not tough. So, to do what I’ve said above is probably near impossible for most – because it takes an unwavering confidence that likely takes years to develop. I want to say that’s confidence is building.
I don’t know that I’ll have that 100% confidence tomorrow, but every day I feel a little closer to establishing an agency with a client base not funded by bosses, but instead funded by friends – with common goals and trust.
Everything Else Can Break if You Focus on the Work
I feel like I’m doing a ton wrong. HR, hiring, training, pricing, business development, longer term strategic thinking. But throughout that, I’m focused on the work.
If the work is good, and the work is continually aiming to get better – and is – everything else will work out. The leads will pour in. You’ll have the opportunity to break down in other areas. But if you master everything else and the work suffers, so will the business. I feel like I’m bad at a ton of things. But we’re doing great. And I think that’s because we’re focused on the work.
I’ll probably never be able to spend a day thinking about designing a fancy office. Because I know I can spend that time doing a little better work instead. That’s not to say that there isn’t benefit to a fancy office – there is – but if at a sacrifice to the quality of the work, it’s not worth it.
To Another Three – And Another 30
I can’t begin to predict where Siege, or myself, will be in three years. Or where I will be in another thirty. I have no idea what kind of work we’ll be doing. Or how big we’ll be.
What I know, though, is that if I’m working with a group of amazing people creating great work for great people, I’ll be happy. And if I’m lucky, I’ll be saying no a whole lot. And less things will be breaking. But if they’re breaking, that’ll be okay, as long as we’re focused on the work, and that work is good.
Okay, maybe not good – great.
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