Are you the boss from hell?

You’re a freelancer and one of your dreams has come true. You’re your own boss. 

Be careful. Being your own boss comes with a serious health warning.

This is your survival guide (so you don’t end up hating every minute of it). 

Ever sit with a bunch of friends or join an online chat where someone is talking about how their boss DMs them Friday evening with a Monday-morning deadline? Or plays favorites? Or takes credit for your ideas?

Bosses can be the stuff of nightmares.  

But not all bosses. Some of them are the making of you. They are kind and empathetic and life-changing human beings. 

I’m talking about the bosses who squeeze you like a toothpaste tube and dance on your boundaries. 

That’s a big reason being your own boss has such appeal. Escaping that B.S.! 

Which brings us to…

The terrible truth

Freelancers make terrible bosses. 

They make themselves work through weekends to hit deadlines, expect themselves to check messages before they go to bed, get slightly sick when they even think about a long vacation, and they never seem to have enough for a pay raise. 

And it makes no sense. They can be the perfect boss but they instantly become everything they ran away from. What went wrong?

The Two Yous

A lot of client problems come down to boundaries. It’s exactly the sa​​me in your business except with a twist of extra difficulty.

The crux is, you’re now both employee and employer. And the line between the two doesn’t exist until you draw it. You need to draw that line.

Here’s an exercise I want you to do. 

Make a list of things you absolutely do not want to do as Employee You. That might be working important family days, postponing holidays or putting up with rude clients. 

Make a list of things you’ll do because it has to be done. Like working every weekend running up to Black Friday, because that’s your clients’ big payday. 

Now, before we go any further, let’s get real for a second. You still might have to do some of these, but now they’re bracketed off – they’re the exception, not the rule. Boss You now knows these are BIG asks and has a very clear set of red lines to respect. Now for step two.

Build for Boundaries

If you want four weeks off in the summer, then it’s your responsibility to land enough clients to make that financially feasible. Employee You needs to be pretty hard-nosed about that. Don’t take excuses from your boss. You two have a deal. And you do what you say you will, right? 

(Again, I know life gets in the way. I know sometimes we do stuff we don’t want to because we have to. This is about intentionally designing your business to avoid that as much as possible.)

Here’s how that works for time off.

If you want a month off every summer, another week over the Holiday Season and another week for discretionary days, that leaves 46 weeks. If your gross revenue target is $100,000 (it’s always $100,000 🙄), you need to bring in $2,174 a week. If you work 25 client hours a week, you need to charge $87 an hour as your internal rate. 

(And that’s if you’re fully booked out, so adjust by 10% or so to allow for calendar gaps.) 

By setting those vacation-day expectations, you have the information you need to respect them (the internal hourly). Do your job as a boss (getting clients), and you’ll have no problem honoring your commitment. That’s what good bosses do.

Now, let’s kick it up a notch. Let’s be awesome bosses.

How many hours a week do you currently block off for your professional development?

Or do you just squeeze that in?

Same here. 

Most of us squeeze in our professional development. And it’s often stuff we need to know for our next project. But how would we do it if we were a human resources expert?

HR has a bad rep. Not getting into why here, but when I found out what a good human resources person actually does, I was super impressed. They help people become high-performing, happy and engaged professionals. (Seriously, that’s their job.)

I want you to take a page from their book and do this exercise. 

In the same way as you have a five-year vision of where you want your company to be, take time to map out where you want your skills and competencies to be in the next five years. Those abilities should map well to your business ambitions. If not, you need to rethink one or the other or both.

Once you have a list of what you need to learn, pick out what you’d like to focus on for the next year. Then identify the resources, including costs and time, you need to do that.

Now your business has a professional development budget and you know how many hours a week you need to allocate to that.

Build both into your budget.

Let’s say it’s five hours a week you need to take from client work. That means your internal hourly (from above) needs to be $109. Or, you work an extra 5 hours a week. Most of us will take the five hours extra if our home lives allow it. 

And that brings us to…


You need to reward yourself for the work you do. All of it.

If there’s an extra five hours for professional development, you need to pay yourself for that. If you absolutely have to cross a red line, you need to pay yourself big for that. 

Yes, you might not be able to do that right now. You mightn’t have the skills yet or have figured it out. That’s ok. We all need time. Never beat yourself up because you’re not there yet. 

But if for five years in a row you had to work through your holidays, it’s time to change things up. 

An Accountability Partnership

Being a freelance owner is a partnership between Boss You and Employee You. You both have responsibilities and you need to hold each other accountable. Again, copy from HR.

Run annual evaluations and professional development meetings (put them in your calendar). Are you a great boss? Are you a great employee? What support do you need to be better? 

The key to all of this is intentionality.

If you want it, you can be the most amazing boss you’ve ever had. That’s in your hands, which is something no employee on the planet can say.

This was originally sent as an issue of my weekly newsletter, Breakthrough Beat.
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And so you know I can walk the walk…

Are you ready for clients who bring you interesting projects and higher fees? A bank balance that means you don’t have to worry about what happens in the next 12 months?  

Then know this…

Getting there isn’t luck. It’s the result of deliberate steps that follow well-proven paths to success.  

I know those steps and I know those paths, and I’m going to show you both, starting today.

As long as your business is client-based, your success – and the size of your bank account – is tied directly to the quality of clients you attract.

Hi, I’m Amy Posner…

  • I’ve coached hundreds of creative freelancers to success
  • I’ve built six businesses, all highly profitable
  • I’ve owned and run a micro and a full creative agency
  • As a freelancer, I’ve had multiple $200k+ years
  • My businesses have sailed through the worst economic shocks the last 30 years could throw at them

And now I’m going to share everything I know with you about building a resilient and rewarding business that delivers on the full promise of your talent.

LEarn more about working together  →

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