5 Biggest Lessons from 5 Years in Business

March 14, 2014: my last official day at a j-o-b.

Actual footage of Baby Whit and my “goodbye pavlova” from my leaving lunch:

I remember cleaning off my desktop, shutting down my computer, saying goodbye to my coworkers and thinking:

Oh, sh*t.

I had no idea what was going to come next.

Over these last five years, my copywriting business has seen a lot of changes…

From charging $20/hour for basically whatever marketing task I was reasonably capable of doing (web design, graphic design, social media content)…

To discovering that what people needed help with the most was copywriting…

To sharpening my skills by working under various digital agencies…

To writing in 98 client voices…

And watching my life change right along with my biz — moving six times (one international), losing my dad, and getting married.

And while I certainly don’t have it all figured out…

I do have a multi-six-figure copywriting business with 90% of my clients wanting to work together again. So I must be doing at least a couple things right. Right? 😉

I’ve been reflecting over these past 5 years and distilling the lessons into a few takeaways I can stick in my back pocket. Because I don’t know about you, but I prefer to keep my focus narrow, rather than trying to juggle #allofthethings at once.

Here are the 5 biggest lessons I’ve learned that I’m taking with me into Year 6:

Success comes from DOING, not thinking.

I’ve worked with some insanely inspiring clients over the years. And the ones who are making the money and impact they want to be making are the ones who focus on doing.

They’re more about jumping than endlessly strategizing about the jump. They think juuuuust enough to make a plan and then get after it.

As a chronic over-thinker, this is a lesson I’m still learning. But it’s one I’ve taken on board, loud and clear, because there’s just no denying it.

In order to make moves, you HAVE to believe in yourself. Seth Godin says you can’t wait to get picked — you have to pick yourself.

You’re the only one who can do this for you. Continuing to take action takes major confidence, self-esteem, and self-belief…which isn’t easy by any means. But in order to build the business that you want, you’ve got to do it…and keep doing it…every dang day.

Adopting the attitude of “so what?” helps a lot here.

If you fail, so what? If you mess up, so what? I’ve listened to enough titans to know the real secret is to “fail fast”…and you can’t do that without getting moving.


B+ work is A-okay.

I read a post by Rachel Rodgers recently that said anything beyond “good enough” is inefficient and a waste of your precious energy.

It jarred me because it’s such an unfamiliar concept for someone who literally moved single pixels for DAYS when designing my logo. But the older my business gets, the more I think she’s right.

I still believe in doing your best and not walking away until you feel proud of the work you’ve done. But more and more, I also believe in not holding yourself to an impossible standard.

Not everything needs to be an A+. I’m not quite comfortable with “Cs get degrees” yet (maybe because I still get flashbacks to my friend’s burnout boyfriend shouting it before shotgunning a Natty Light in her college apartment…yick, chills) but I can get on board with a solid B+.

It’s just pragmatism: To make Lesson #1 happen, you can’t be churning out A’s all day, every day.

You also need to take a step back to understand what kind of work can afford to be B+ work (for me: things like Instagram captions and appointment reminder copy) and what needs your full effort (like client work and my program, Welcome Sequence Wonderful.)

When you make peace with B+ work, you’ll free up time and energy to do A-level work that matters most.

Numbers matter.

I worked on my first multi-six-figure launch this year. And the truth? I didn’t do anything differently.

I followed exactly the same process I always use for my launch package and worked in the same persuasion techniques and copywriting tactics and sales strategy I always use. But this launch made, as my friend Mark would say, “buku dollars”.

Why? Purely because this client has a hyoodge audience. His sales messages were showing up in hundreds of thousands of mailboxes.

Seeing this firsthand was incredibly refreshing…

To know that big launches aren’t fueled by some magic fairy dust that only 0.1% of online businesses can get ahold of is so inspiring, isn’t it? They’re built on good, solid copy and tried-and-tested strategy…and all of us can create that! It really comes down to the size of your audience.

So if you’re not making multi-six-figs with your launches, it’s not because you completely suck. (Good news, right?!) It’s likely because you need a bigger audience.

Building an audience is something I wish I was serious about back at Day 1. But as the Chinese proverb says, “The best time to plant a tree was 20 years ago. The second-best time is now.”

If you want to be able to scale your income and impact, grow that audience, bud. Next to the quality of your product and your marketing, it’s the most important factor for your growth.

Slow and steady is a differentiator.

In online business, we tend to focus on fast.

“I made six figures in six months!”

“My launch brought in $72K in four days!”

“I grew my audience to 15K in four short months!”

You don’t often hear about the years and years of hard work that came before the flash. There have been many times I’ve compared myself to others who are moving faster than me and felt like I’m lacking.

I have to remind myself constantly that I’m not shooting for the same target. The whole reason I got into business for myself is because I want something different out of work and out of life. My goal is to build something solid that will support me for decades — through seasons when I want to be a boss and seasons where life takes precedence — not a fast six-figure year.

The older I get, the more I believe in the power of slow, whether it’s in business or in a cup of coffee and a book on Sunday morning. Not only is slow “okay”…slow is preferable. Slow is real. Slow is good.

And in a world where it feels like everyone looks the same, opting out of the “overnight success” track for the slow + steady route is a way to stand out.

The quick hits won’t last — I’ve watched a few fizzle out in just the last few years. So if you’re growing slow and steady, congratulations! That’s a great sign you’re building a strong foundation that can support future growth.

Work doesn’t have to be so hard.

When I was in first grade, I had a traumatic experience where I had to stay up suuuuper late (probably like 8:30pm or something 😱) to finish an assignment that I’d left to the last minute.

I’ve always thought this was a genius parenting move on my mom and dad’s part because it taught me to do work first, then I could play…or else I’d screw myself in the long run. So for the majority of my life, work had to come first. If I had time after all that, then I could have fun.

And while that lesson helped me a ton along the way, it’s not coming with me into Year 6 of my business. What IS coming is the idea that work and fun can and should be intermixed.

Not every day, not every task. (I’m not Willy Wonka here, not everything can be rainbows and chocolate.) But it’s possible to find little ways to bring more pleasure into my business…and I’m actively seeking it.

Little bursts of fun make the days go faster, help me get more done, and make me feel better while doing it. The world doesn’t come to a screeching halt if I take five minutes to make a nice cup of tea before starting my blog post.

As a business owner, sometimes it feels like every spare minute is taken up with work. There may realistically not be much time for fun some days. Life’s too short not to enjoy the ride so buffer in moments of pleasure throughout the workday.

(If you need ideas, here are 6 ways I mix business with pleasure.)

And while we’re on the topic, “no” doesn’t have to be so hard, either. My coolest launch project to date with a total dream client came because I emailed her and pitched myself. I knew the worst that could happen was I’d get a “no”…and the best that could happen is that I could get to work on a huge launch with an inspiring team of people (which is exactly what happened.)

If you tend to take your business really seriously, a) I really love you for that, but b) we really should lighten up. It can be so much easier, if we let it.

Phew, boiling down this list was harder than I thought! But it never helps me to have a zillion things to keep in mind; I need just a few concentrated points to focus on.

Less is more, after all. (👈Which totally would have been Lesson #6, if I let myself break the rules and have 6.)

If you’ve got any more drops of biz wisdom, I’d love to hear it in the comments below — please share!

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What’s one of your hard-won business lessons?

What’s a great piece of advice a mentor’s given to you?

How do you incorporate it into your life + biz?

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© Whitney Ryan LLC

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