The Two “Boss Trades” Every Creative Freelancer or Entrepreneur Makes

Leadership, Productivity, Professionalism | 0 comments

When you’re considering launching a creative freelance or entrepreneurial career, the appeal of “being your own boss” is very real. After all, you’ll get to work when you want, take vacations when you want, work with whomever and wherever you want, and much more.

However, there’s a very fatal assumption many of us makes that sounds like this:


“When I’m my own boss, I won’t have a boss.”

I hate to break it to you, but this is utter lies! Garbage. Rubbish.

When you become your own boss, you make twoBoss Trades”. Let me explain:

First, you trade a conventional boss, you know…the Michael Scott type…for dozens, hundreds, and maybe even thousands of tiny bosses. These tiny bosses are your clients or customers. Sometimes, these tiny bosses can be even more demanding and more unreasonable than a typical boss might be. Ideally, you’ll earn great clients and have great tiny bosses, but this is not always the case. Even great client bosses will give you deadlines, check on your work, reprimand you when you go astray, and sometimes ask for unreasonable things. Instead of some Bill Lumbergh type asking you to work on a weekend, your clients will.

Second, you trade a conventional boss for the boss in the mirror. You become your own boss and guess what?…you have the potential to be a horrible boss. When you’re your own boss, you might work yourself to the bone, place unreasonable expectations on yourself, make yourself work late into the night or skip your vacation to finish a project. You might kill your own morale, make yourself work the wrong jobs, and maybe drive the business into the ground to the point you have to lay yourself off and make you get a conventional job.

These are the two “Boss Trades”. Instead of having one typical boss, you have tiny client bosses and you have the big “you” boss.

As someone who has made the two Boss Trades, I can say it’s worth it. Although the freelance or entrepreneurial route is definitely not for everyone, and there’s zero shame in working a so-called “traditional job”, being your own boss does bring a lot of freedom. But, as I mentioned, it brings some great dangers as well.

Here are eight simple tips to minimize the dangers of the two “Boss Trades”.


When it comes to working for the tiny “client bosses”:

  • Establish clear expectations – when you work for clients or customers, you have the opportunity to set clear expectations at the beginning of your relationship. You get to determine/negotiate how much they’ll pay you, when they’ll pay you, how they’ll pay you, what the “scope” of the work will be, when they can expect to receive it, how they’ll receive it, and more. Setting clear expectations (usually in the form of a contract or proposal) will eliminate the majority of the dangers of the “client boss” relationship.
  • Communicate Often and Clearly – Your customer or client bosses want to know what’s going on. Don’t ghost them for days or weeks. You can keep them happy by communicating with them often, being clear as possible, and being thorough. Nothing makes these tiny bosses happier than when their emails are answered quickly and completely.
  • Be Friendly – Don’t be a jerk to your customers or clients. Be friendly and kind (even when they are not friendly to you). Being likeable goes a long way.
  • Meet your Deadlines – this is a no-brainer, but so many creatives get this wrong. Meet your freaking deadlines. Just do it. If you established clear expectations for this upfront, then this shouldn’t be a problem. If you find yourself working through the night to meet a deadline, then next time negotiate for a longer deadline or an adjusted delivery schedule.


When it comes to working for the big “boss in the mirror”:

  • Track Your Time – As a creative, your time is your most precious, most finite resource. Track as much of it as you can. I elaborated on this in an earlier blog post, so please check it out.
  • Set Boundaries – You have the power to establish boundaries or guardrails in your life. Pre-decide when you won’t work, when you’ll take breaks, the types of jobs you’ll take, and more. If you don’t set boundaries, the freedom that comes with being your own boss will all but evaporate. Boundaries = freedom.
  • Keep the End in Mind – Keep a laser focus on why you’re doing this and where you’re going. This will help keep your morale up and give you the discipline to take the kind of jobs that will get you one step closer toward your end game.
  • Schedule in Renewal Time – Lastly, you must save time to do things that renew your mind, body and spirit. Sounds a bit “woo woo”? Well, it isn’t. You are more than your work. If you don’t step away from your work to do things that fill up your soul, eventually your work will suffer. Take vacations, exercise regularly, invest in your spiritual life, meditate, pray, enjoy your hobbies, read great books, see friends and family, etc. The more you renew yourself, the better your work will be and the more you’ll enjoy it.


If you’ve decided to trade the conventional boss for the two unconventional “client” and “you” bosses, then good for you. It’s a hard road, but a fulfilling one – if you treat these bosses well.




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