The biggest fuck ups I made in my first year of business

Vanessa Green
September 10, 2021

It's been a minute since I started this consultancy - well, 525,600 to be exact.

And during those minutes, I've made millions of decisions,  some based on insight and experience and some based on my gut feelings alone. Not all of them, unsurprisingly, worked out in my favour.

I'm not going to bore you with how awesome my first year has been (though at times it has been great), but I want to share the hurdles, the challenges, the downfalls of starting your own business. Because a lot of the time, it's exhausting and anxiety-inducing and comes without any safety nets.


Plus, let’s be honest, who doesn't like to hear about how someone else fucked up?  The Schadenfreude is real.

So here we go, in no particular order.

1) I didn't sort out my pricing

I hate pricing. There, I said it. I find it overwhelming, and I imagine I always will. I'm either terrified I'll lose business by pricing myself too high or undervalue my services by charging too little. There is no middle ground. I've researched value-based pricing, project-based pricing, hourly pricing (which apparently you should never do), and I'm still no closer to finding a model that I'm comfortable with.

When you work a full-time job,  you have one pricing conversation, and it's about your salary when you start (and maybe a few more over the years when you negotiate a pay raise). When you work for yourself, you have this conversation with every new client or for every new project. It's incredibly challenging to know how much to charge, how much of your time the work will take and how to base your cost not just on your time but also on your experience.

I have yet to figure this one out. And I know it's still hurting me. I’ve probably lost a lot of potential revenue over the last 12 months, but it’s something I’ll have to wrestle with for as long as keep working for myself.

2) I hired a shitty accountant

When you start a business, you want to find service providers that you gel with. That get you. That support you and genuinely want to help you.

Unfortunately, not every service provider is cut from the same cloth.

My first accountant made me feel like a total idiot every time I asked her a question.  It made me avoid her and not want to pick up the phone to talk to her. But when you work for yourself, avoiding your accountant really isn’t going to fly. I would go months without hearing from her.  And I would get invoices every month, but I never really knew what I was paying for.

Eventually, I ended things and got a new accountant. But I wish I had spent more time vetting her and knowing what to look for. One thing I have learned in business is that the age-old adage is true: you really don't know what you don't know.

3) I waited too long to put together a client contract

Knock on wood, I've been lucky enough that I haven't had a client stiff me on payment. Yet. But I know it will happen someday. And whether I decide to take their ass to small claims court or not, at least I know I’ll have some legal leverage by having a client contract set up.

When I started my business, I thought, “Well, I haven't been stung yet, so I'll just wait it out until something bad happens and then get a contract in place.” Clearly, though, that's specious reasoning.

What if I got screwed over on a huge project that I had spent hours on? What then?

I also took too long to define my payment terms on projects, which are now 50% upfront. This means in the event I do get screwed over by a client, at least I won't be totally out of pocket.

4) I offered services that I didn't really like doing

Defining your services is difficult - I have services I sell that I don't advertise - and services I advertise that I don't actually do very often. But when I was first starting out, I threw a bunch of stuff to the wall and waited to see what would stick.

Turns out, I don't LOVE creating content for social media. Especially because I see other people do it much better than I can, and I realized that it is not one of my strengths. It's also such a specialized marketing channel now that I don't think I have the skills to do it justice.

After getting a few inquiries about social media management, I realized that I didn’t actually like doing it. When you first start out, you want to say yes to everything and you’re scared to turn anyone down. But now, I politely decline the offer and refer to them a network of other very skilled social media experts who are better equipped to help them.

5) I took too long to learn to say no

I took on projects I didn't like with clients I wasn't a good fit for because I was scared of losing money. There probably isn't a freelancer alive that hasn't done the same thing. But I’ve learned that it's not all about the money - it's about your reputation and creating a client base that reflects your skills and values. Knowing when a client isn't a good fit - or when a project isn't right - is so incredibly important to the longevity of your business.

I still haven't 100% figured it out, but I hope I have many years ahead of me to get it right.

I got some stuff right, too - but you can’t rest on your laurels in this game. You have to fuck up, learn from it and move on. Like that time I hosted my first webinar and shared the wrong screen for the entire hour. That kind of shit keeps you up at night. I’m sure I’ll have more fuck ups as the years roll on, which will make for great stories and help keep me humble.

Happy 1st birthday, Greenlight Content! 🎉 Here’s to many more!

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