If You Have Clients Are You Really Your Own Boss?

The prospect of being your own boss is very exciting to most, but for those who go into a line of work where they have clients, the line gets a little blurry. Where do you draw the line?

I am reminded of a client from hell. Imagine (some won’t have to I’m sure): 3 hour calls, scheduled to be 1 hour, for which he was 1 hour late, on which you get nothing accomplished, during which others are conferenced in and out (w/out prior plan), and finally, all while being borderline verbally abused. Bullshit meetings, insane leadership and rarely accomplishing anything. Pair that with a silly title within their organization, and a staff of contractors they hired for me to oversee - Yeah, things got blurry. I might as well have gone back to my government job.

Surely this is a worst case, but let’s start with where most people agree—Working for someone else sucks.

There’s a reason that a huge amount of comedy is devoted to “dumb bosses”. It’s something that everybody can relate to sometimes. From the pointy-haired antagonist of Dilbert to the droning inhumanity of Office Space’s Bill Lumberg, incompetent managers hold a special place in society’s contempt.

A lot of us in the freelance/business owning spectrum like to proudly display our independence as something we have over the average “office drone”, but does it really mean anything? Are we really any more free than they are?

After all, for everything that they put up with, you can’t argue with job security, clear avenues of advancement, actual human relationships…It’s pretty easy for them to say that they don’t dance any harder for their dinner than we do. And if that’s true, what do we have?

So what does it really mean to be your own boss?

What Sets You Apart

The self-employed do experience a much different lifestyle than the old-fashioned company man, but it’s not because they are in a permanent party-mode free of responsibility and obligation. In fact, most of the differences between the employed and self-employed are just that: responsibilities.

Even when you’re self-employed, you still have to get your work done and deliver it in a timely manner (assuming you count feeding, clothing and sheltering yourself as priorities), but you also have to do it while taking complete charge of your quality and motivation.

These are only some of the responsibilities that you have to take on when working for clients.

  • Finding motivation (which is a hell of a lot harder than it sounds)
  • Taking full responsibility for any unforeseen emergencies
  • Constantly searching for new clients to fill the gap when the old ones leave
  • Dealing personally and often without legal recourse whenever payments aren’t made
  • Knowing that vacation or even a day off often means less money in your pocket.

Why Am I Doing This Again?

Congratulations. You have no boss. Big, f’g deal. Now you have to deal with more BS than most Salaried Men/Women could even imagine. Do you find yourself re-thinking your life? Well, don’t quit the day job just yet. There are reasons that we do this, even if it doesn’t really mean the 24/7 bachelor life. Oh yeah, I thought so, too.

This is why we love what we do, and wouldn’t have it any other way.

No Bureaucracy

Those of us who have worked in the office world know what this word really means. It means doing something in a dumb way just because someone’s pride relies on it. For tradition, for the comfort of the outdated, or just because a certain manager takes immense pleasure in making you do useless things to prove his or her superiority.

Being independent means having the right to be on the cutting edge. Hell, most of your clients expect it. Show them something new or expect to be replaced by someone who can. For those who like to live in this world, it’s intensely exciting and creatively fulfilling.

No Monotony

Ok, that’s not always true. In leaner times, you do what you have to do. In most cases, though, it’s a choice. If you aren’t constantly facing new challenges, it’s probably because you aren’t hunting them down. In the office world, it can be a lot harder to find new challenges because it means begging or playing politics with the established cliques. Which of course brings me to…

No Drama

Stacy’s dating that boy from the copy room? Oh the scandal. Ted’s making the rounds with new baby pictures? Better think of something nice to say if you want a good performance review. Oh shit, here comes your rival Todd, smirking because he just landed the Johnson account you wanted so much.

Now imagine that all of those people suddenly disappeared and you were left with nothing but blessed, efficient silence. Even with all the other great benefits, there is little that beats this. Your business is your business, and nothing gets in the way or blends into your personal life.

No Salary

This year you make 65k, and next year, if you work your tail off, and kiss the right amount of ass, you could make 70k. Ten years from now you’ve made it: 100k/yr, benefits, and absolutely no chance of further advancement.

As a self-employed individual, you control your salary cap. You decide how much, or how little you make. How much you are worth annually is up to you.

Did you know that in America there are 30,000 1 person businesses making over 1MM? Even if money isn't your motive, that’s got to light a fire under your tushy. The sky is as high as you are willing to reach.

Why we do this is a very simple question to answer. Less simple however is how we intend to hold onto it.

Drawing a Line in the Sand

Being your own boss is hard, but it has meaning. If you want to reap the rewards, you have to remember to keep yourself in control. This is a skill that takes a long time to master, but until then, just remind yourself:

They Hired You

Remind yourself, your clients value you and your expertise enough to part with their hard earned currency. They have contracted you because you have convinced them that they can trust you to get the job done. They didn't hire your dick head competitor who undercut you, nor that big fancy ad agency. They hired you. You. You impressive, ridiculously talented being, you. You, you, you. Don’t let them forget it.

Value your Time

Why do you sell yourself so short? If you haven’t figured it out yet, your most valuable commodity is your time. It is irreplaceable. And yet, you are letting your client run your calendar? The next time they ask you for a meeting, even if your calendar doesn’t have a dot of ink on it, you tell them you are going to check. Have a good, hard look. One-one-thousand, two-one-thousand, three-one-thousand, sir, I can FIT you in at 1PM, 2 days from now. Perception is everything.

If your client does not value your time, they do not value you. If they do not value you, you’re f’d. Worse, you will have only yourself to blame.

Pull on the Leash

I recall picking up a client who had previously been working with a friend, and colleague of mine. When solicited, I contacted Jeff, and asked him what was going on. He said something like “tough love.” and “he will be back.” Shortly after landing the client, I asked Jeff if he had any warnings or recommendations for me. He said something like “You have to be firm with him. Train him. Like a dog.” Excuse me?!

Well, at the time, he was my biggest client, and I let that pooch walk all over me. 30 days later, he walked right back to my friend.

Many clients later I finally understood what Jeff was telling me.You need to remind your client that you are the boss. Show them what they can expect from you, what you expect from them, and the consequences should someone (namely them) step out of line.

It is easy to buckle, especially because you want their business. However, in my experience, you are more likely to lose their business if you lose their respect. It’s not easy, but you absolutely must stand your ground.


I am reminded of my younger brother. He was the master at throttling my mother’s expectations of him. He would put forward his minimum effort, occasionally falling below that, and then when she was on her final straw (and he knew before she told him), he would miraculously be awesome. But how awesome? Not very. At least in my eyes. All he did was slightly surpass his minimum effort, but because my mother had been trained to expect so little, when he over delivered, she lost her mind, and showered him with love and gifts. I love my mother, but when it comes to my brother, she is totally clueless.

You are a firm believer in over-delivering. Going over and beyond for your client is part of your value proposition. Mr. Over-achiever, you are doing it wrong. Every time you raise the bar a bit higher, you make it that much easier to fall below it. It’s a vicious cycle, and the only thing that is sure, eventually, whether they know it or not, you will fall short.

Your client doesn’t see your bonus deliverables as that. Even if you go to lengths to explain how you exceeded goals/expectations, in their mind, whatever you just did becomes the new norm. The new minimum allowable effort.

There is nothing wrong with serving up a large bounty for your client, but it must be managed. Even if you don’t charge an hourly fee, start keeping track of hours spent on the account, and what you did during that time. Check out Harvest or Toggl. You may just find out that you are spending so much time, you are hardly profitable. Beyond that, I would be as clear as possible, early on, as to what your deliverables will be. Refer back to them occasionally, and it wouldn’t hurt to remind the client what they are.

Be the Boss

This will never be easy. However, it can be intensely rewarding. Never forget that being your own boss comes with serious challenges, and that you need to be ready to embrace those challenges if you want to succeed.

Take control of your time, take control of your quality, and take control of your clients.

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