The 5 Big Lessons I’ve Learned From Owning My Own Business

In January of this year, I celebrated 4 years of owning my own business. I can’t believe it’s been that long; more importantly, when I look back, it’s insane to think about how much the business has evolved (heck, how much I’ve evolved). In the spirit of chatting more about behind the scenes business schtuff around here, I’ve been reflecting on some of the biggest lessons I’ve learned from running my own shop. While oftentimes tough to integrate, thinking about their outcomes now, these nuggets have also gotten me through the roughest of days. Here they are!:

Forgive yourself

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We live in this culture that’s encouraging us to dream bigger, to hustle, to always be doing and growing. It’s rocket fuel for the even marginally ambitious person, but I truly believe that once this messaging permeates your daily subconscious, it can also be paralyzing and even detrimental. How so? Well, if you’re anything like me, when I’m not dreaming bigger or hustling or doing or growing, I tend to be really hard on myself. I get that nagging voice in my head that says I’m not doing X enough, or I should have done this, or why didn’t I do that. Is that voice familiar to you, too? It makes me effing miserable.

I’ve learned to combat it by saying to myself: it’s ok, I forgive you. Maybe that sounds totally new age cheesy, but it works. Sometimes at the end of a long day, where I’ve powered through 95% of my to do list, I’ll look at the one or two items left and think, ugh, if I had woken up an hour earlier, I could’ve tackled those. It’s taken some time, but I then try to tell myself, it’s ok, I forgive you. Truth is, I probably needed the extra hour of rest, those items will get done first thing tomorrow, and most importantly, not finishing two things doesn’t take away from the success and accomplishment of completing all the others.

Try this a few times, and you’ll get really good at it. I’ve learned to forgive myself for not posting here more, or to Instagram more, or documenting more of my days on Snapchat, or even tackling all these growth strategy projects for my business. I figure I’ll get to them eventually, and even though I still battle that minor panic about not tending to the right parts of the garden (so to speak), as a solo business owner, you really have to step back and be comfortable with the discomfort.

Another way to look at forgiving yourself is that you don’t have to be good at everything. Which leads me to a lesson that’s equally as important:
 

Ask for help

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If it wasn’t already obvious, asking for help for things you know nothing about is generally a great idea. Lawyers? Yes. Accountants? Oh, hell yes. Some of the best investments I’ve ever made in my business were for professional services that not only saved my sanity, but quite literally saved me money when it was all said and done.

But what about the things you (think you) rock at? Ever thought about asking for help on those? To be honest, I never had, until my business had grown and I was doing way too much and on many days, didn’t feel like I was doing any of it well (it’s ok, I forgive you). In my head, I was the most organized person, could put new systems in place to streamline, and still manage everything as well as I did 3 years ago with a much smaller client base and different business goals. In other words, I was out of my mind.

I made the mistake of waiting about 6 months too long before hiring an assistant. But welcome to business lessons in the making over here: I actually hired someone just last week, and even though we are in the process of establishing our systems and workflows, I can’t tell you what a boon it’s been. Just mentally handing things off to her has put a pep in my step — I feel like there’s a whole subset of things I soon won’t have to fret over, and that makes me feel a lot more productive and excited about the tasks I do have to work on in a single day.

For whatever reason, sometimes it’s really hard to ask for help. I don’t know why it took me as long as it did — maybe it’s related to my third lesson, below — but if you find yourself in the position of repeatedly convincing yourself that, it’s cool, I’ve got this while simultaneously feeling panicked on the daily, it’s probably time to hire someone to help you.

Be both humble and proud

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The comparison trap can be a real bitch. I’ll have weeks where I feel like I’m killing it, and others where I’m having mild panic attacks about every decision I’ve made over the last four years, and awful internal criticism over the things I’m creating. I think both feelings can be detrimental — especially if you’re letting them rage on unconsciously — but both can also be really helpful. Let me explain.

I think there’s a constant tension that exists when you’re running your own business, not to mention putting your creative work out into the world. You have these victories that make you feel like a total boss, and then crippling moments of self-doubt. I used to think of these phases as really binary things, like either I was on top of my shit, or I was a complete failure. I’ve learned instead to let them both exist together, though I’ll admit, it takes some work. For example, when recently nitpicking over a bunch of design decisions I had made and internally lamenting my ineptitude (ha, not really, but kinda sorta?), a former client happened to reach out to express her appreciation for the work I’d done, and what a success she felt the project was. It was instant validation of my work, sure, but it also reminded me that the nitpicking pointed to something else — I was growing and improving.

It can be tough to do, but I’m constantly working on letting my Internal Critic and Queen of the World mentalities exist together, in harmony, because that’s when I feel propelled forward. If one side goes unchecked — say, the Internal Critic — it can become paralyzing, where I’m questioning myself, can’t properly advise clients, and also feel completely stuck in my business. The self-criticism turns into self doubt, which is no bueno. Similarly, on the flip side, if I’m overly confident that this machine is running itself, I feel like I miss potential opportunities, or don’t open myself up to new learning experiences. You really have to let both sides coexist, because they feed off each other. Maybe another way to think about this tension is having confidence in both your work and yourself.

Go with the (brain) flow

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I was hanging out with my friend Jillian recently (a fellow small business owner) and she mentioned how she had had one of those days where she couldn’t force her head to focus on work or any of the tasks at hand. So she gave up and went downtown and went shopping. As she should have! I reflected back on my days of working a traditional desk job, and was considering how I’d given my brain down time at work back then. Visions of meetings that were irrelevant to me flashed through my head — I mean, does this sound familiar? You’re sitting in some two hour meeting that doesn’t really impact you, and your mind is wandering. Or you have a free hour at work and find yourself catching up on news items. You need a break from what you’re doing, so you find ways to build one in.

I think no matter your job or the size of your company, it’s human nature that sometimes our brains are just not tuned in to the type of task in front of us. I have days where I’m feeling incredibly creative, so I try to harness that energy and focus on creative tasks. Some days I feel prolific, so I’ll write a longer blog post (hi!). Other days I can’t put a sentence together to save my life, so maybe I’ll focus on bookkeeping or analytics. It can suck when I have deliverables due and I have to complete a task I’m not feeling wired to do; on these days, I’ll give my head a break and go for a walk or go to the beach for an hour to clear out the cobwebs and come back new. Bottom line is, you really have to stay aware of where your head is and go with the flow, because it ultimately results in a more productive day.

Never stop learning

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It’s not exactly a secret that the Internet is always changing. I once had a client joke with me that she’d see me again in 18 months, because with new design and web standards, that felt like the frequency with which one had to overhaul a website (on that note, stay tuned for changes around here!). With business and personal life a constant blur, one thing I’m working on implementing time and systems for is to keep on learning. Sure, there’s a fair amount of ongoing learning that happens naturally via researching things, reading new resources, all that. But I can’t tell you how many times (or how many bookmarks and folders) I’ve saved with articles and different tools that I never get around to fully researching, let alone integrating into my work life.

There are two small things I’ve recently done that I’m hoping will combat this. For one thing, Lisa (who I work with on the vast majority of my web projects, as my developer) and I have created a couple different repositories for cool resources or ideas we come across. We both work in Trello, and have a shared board related to clients, as well as resources. We also communicate throughout the day on Slack, and love sharing awesome links and ideas to try via a #resources channel there (also, Slack! — it’s completely changed my workday chat life).

The other thing is I’m planning on taking off a large chunk of time over the summer. No vacation planned — I simply want to block time to go through all these articles I’ve saved, think about my business more broadly, and strategize a little bit. Like business spring cleaning, except, in the summer. I think you have to prioritize that learning time, otherwise it gets shoved to the back burner.

And here’s the thing: prioritizing that time and discovering new resources gives me life! It’s so invigorating and inspiring.  You come across some new tool or idea or way of doing something, and it makes anything seem possible. It’s especially true in digital industries like mine, but I honestly believe it can be true in any job or career path. Life long learning, y’all, it’s key.

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Pretty sure I could come up with at least five more big business lessons, but these are the ones that have been on my mind as of late and that I find myself constantly repeating to myself. What about you? Regardless of where you work, what are some of your biggest career lessons?