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It sounds bizarre, but I really do mean it: sometimes, you just have to be “difficult” to work with. Let me tell you why.


What it means to be ‘difficult’.

Some people don’t like it when you do things the right way, whether it’s incorporating, getting your lawyer to review contracts, or having an agent negotiate on your behalf. It changes your status from “yes” to “hold on a minute”. And it will absolutely make you look difficult in the eyes of people that don’t want you to do things the right way.

And, in that case, you’ll likely be perceived as being ‘difficult’.

Good! Because anyone who has a problem with you doing things the right way doesn’t deserve your business. If anything, that’s a major red flag.

Don’t be a jerk.

Of course, some people are ‘difficult’ in the sense that they’re total jerks. They’re bossy, they’re lazy, they’re a pain to deal with. This isn’t what I’m encouraging you to do!

There is a fine balance between being kind, and asking a lot of questions to get something right, and being cold, and badgering people for answers. If you’re in a leadership position, there’s also a fine balance between leading, and being a tyrant.

The best way to know if you’re a jerk, or if you’re just being perceived as difficult is to ask yourself: would you work with yourself? Would you tolerate your own behaviour? Are you trying to make someone else’s life difficult on purpose?

Work with professionals, not sharks.

You should also only work with professionals that will represent you the proper way. While having a lawyer who’s a total shark sounds great, leave that kind of behaviour to lawyers on tv shows. In reality, you want a lawyer who’s cool-headed and pleasant to work with. You also want an agent who’s well-spoken and good to work with. 

There’s no advantage to you in working with people who are going to intimidate, threaten, or badger other people. That will actually work against you. So, make sure you properly vet your professional team!

Rising up the ranks

People who are at the top of their field have, at some point in their life, been perceived as being ‘difficult’ to work with. Yes, some of them have been complete divas, and they really are a nightmare to work with. But, the majority of them are not. They’re people who have risen up the ranks precisely because they’ve had professionals negotiate contracts on their behalf.

You can’t be a free agent, forever. Eventually, if you’re really good at what you do, you’ll want a team of people looking out for you. And that team will help you rise up the ranks because you’ll no longer be at the mercy of people trying to take advantage of you.

Some friends aren’t ‘friends’.

The expression “it gets lonely at the top” is true. I’ve spoken with a number of CEOs, actors, directors, and leaders who have all echoed this statement. The thing is, when you’re just starting out, you’re likely going to make friends who aren’t going to be as supportive as you get more successful.

Many of them might encourage you to skirt the rules. Some might question you, or mock you, for doing things the right way. Some might even try to drag you down. You really need to surround yourself with people who are also professionals.

Work with the right people.

The right people to work with will never perceive you as being tough to work with just because you’re being professional. The right people will understand that a degree of professionalism doesn’t make you unflexible. It means that they’ll get their best bang for their buck.

Personally, I wouldn’t hire anyone who wasn’t a pro. And of course, that’s just one facet of what I look for when hiring. But, it absolutely makes a huge difference. It shows a sense of ownership and dedication that you just don’t get with more casual contractors.

It comes down to quality.

I remember approaching a famous actor to do work on one of my projects. It was a cold call, we’d never met. She said yes right away. When I asked her afterwards why she chose to work with me, she said that it was because I presented her with a high quality portfolio, and a professional approach to my work, including release forms and a contract.

Contrast that experience, to this: I proposed a project to some more unknown talent, who showed a lot of potential. I was badgered and insulted for proposing that we sign contracts. They wouldn’t sign a release form.

This is what happens when you work with a high quality professional vs working with less than professional people. To the former, I was perceived as trustworthy. To the latter, I was perceived as too ‘difficult’.

It’s an opinion.

Everything I’m saying here is an opinion. It stems from experiences where I have been taken advantage of, and from the stories I’ve heard from other people. From singers who’ve had managers rip them off, to contractors who were paid thousands of dollars less than their equally-skilled colleagues. 

My opinion is this: you have to take care of yourself, and you have to do so in a way that’s professional. And I don’t mean in a ‘suit and tie’ kind of way. I mean in a behavioural kind of way.

You also have to remember that there are always at least two parties in a job. And the best arrangement is one that feels good to both parties. But you can’t know if it feels good to you if you’re not informed.

Information is power. Being informed, doing things the right way, in the eyes of the right people, will make you a superstar. So, don’t be afraid to know your worth, and always remain kind. If you consider yourself a professional, then be one.