How To Become Your Own Boss

Have you ever had that fantasy?

You know the fantasy where you’re the successful entrepreneur who owns the yacht, the lake house, wears the thick-rimmed I’m smart glasses, and has more steaks on the grill than the Hometown Buffet?

Yep, that fantasy… that’s what I’m talking about.

The only thing about fantasies is …that they’re fantasies… they wear off.

And when they do finally wear off you may find yourself elbow deep into a bag of potato chips wondering what happened to your evening, and wherein the Hell is the remote?

Yeah, been there, done that.

Today, entrepreneurship is everywhere. One scroll down your social media feed and you’re bound to see entrepreneurs seeming living the life of your dreams acting as masters of their own universe. With seeing all the highs of the entrepreneurial life and feeling the lows of the 9–5 many of us want to free ourselves from the stale cubicle routine and your coworkers long drawn out stories of their cousin Becky & her affinity for dish soap.

No offense Becky.

The truth is everyone talks about how to start your own business, but few talk about how to be your own boss.

This is where I come in.

Read on to learn the shifts you must make mentally to become your own boss.

Take Responsibility For Your Life

If you want to be CEO of your life you must become the CEO of your life meaning, take responsibility for everything you do. You’re in charge now and the buck stops with you. Let this philosophy marinate into your consciousness and radiate through all of the choices you make. Your mantra is this: You’re the boss, you’re in charge, and you’re capable. Get it, got it, good. Although this advice sounds like a big kumbaya moment with some douche bag in flannel playing the guitar, I must warn you this advice is easy to comprehend but hard to implement. To implement this advice means you gotta kiss your sorry-ass excuses goodbye and hold yourself accountable, which is tough. It also means if you’re not getting the results you want, you’re the reason why which is a sobering thought. Following this advice forces you to grow up and with all growth, there is an element of being uncomfortable. But hey if you want to be a boss, you gotta take the responsibility.

Plan With Purpose

Imagine for a moment that you’re the captain of a pirate ship. You’ve got a peg leg, a bitchin eye patch, one Hell of a dental bill, and a parrot who can juggle. You sail the seven seas and you lead a crew of love-able misfits on adventures… until they find out that you didn’t have a plan… and they throw your ass overboard with the toothpaste they never used. You see, when you’re a pirate captain, above all else you need one thing… a plan. The truth about planning is band-aid simple — if you don’t know where you’re going, how in the f*ck do you expect to get there? Becoming your own boss requires you to set a course of where you want to go on a daily, monthly, and yearly basis. Planning also allows you to do some spot checks to see if you have been staying the course or if you need to audit. Bottom line, if you have no idea where you’re going, don’t expect to get there.

Develop Discipline

Oh, discipline, the practical advice we all run from because it sounds an awful lot like work. To be honest, discipline is one of the few remaining black and white concepts in a colorful, changing world. You’re either doing the tasks you need to do or you’re not and believe me, many of the activities you think you should be doing aren’t well fun. It’s not a walk in the park learning sales if you’ve never done sold anything before. It’s not a picnic working late hours on a deadline when your friends are out partying. The simple fact is when you decide to be your own boss, the work needs to get done whether you want to do it or not. It’s being disciplined is how you can ensure the work gets done.

Know this about discipline, it’s impossible to be motivated 100% of the time, but it’s possible to show up even when you don’t want to. It’s the rolling your sleeves up and doing what you must do is how you get things done. The beauty is if you’re willing to do the hard things eventually you’ll earn a life of the easy things. The mental hack that I do to make discipline more “fun” is to change the thought of “I have to do this task” to “I get to do this task” and that has helped me in stressful moments. I hope it works for you too.

Know Yourself

The biggest irony that exists in this world is being yourself without knowing yourself. This piece of advice feels as if well, you should know it, but many of us struggle with understanding ourselves because we dread the thought of introspection. Rather than viewing this as “knowing yourself” think about it as being honest with yourself. Be honest with yourself in every facet of your life. Be honest with how you like to work. Be honest with the type of work you like to do. Be honest with your strengths and be honest with your weakness so you can become aware of your blind spots. The worst thing you can do is decide to go in business for yourself without really understanding what makes you tick because if you don’t understand yourself, how can you expect to understand others? So take a step back and do some self-questioning and really learn who you are as a person so you can set yourself up for future success.

Get Comfortable Being Uncomfortablee

Unless you have achieved everything you want to achieve, common sense says to get things you never had, you’re going to have to do things you have never done, which is a recipe for being uncomfortable. When you finally decide to start managing yourself, you’re going to have to start wearing different hats many of which you’ve never worn before, and that naturally will make you feel uncomfortable. You must remember that being uncomfortable is only a temporary feeling and the more you do anything, the more comfortable you’ll feel. Get comfortable being uncomfortable simply means accepting that there are going to be tasks that make you uneasy but deciding to do them anyway because it will make you better. With this mindset, you’ll win the mental war and make more progress than all the people who let the feeling uncomfortable keep them planted on the sidelines.

Forgive Yourself

You and I are similar, we’re not perfect. We’ve all done things we would do over and we all had moments that we could have been better in. In order to move forward, you must forgive your past, and learn from your past, so you’re not held prisoner by your past. By forgiving yourself, it will allow you to be more understanding of yourself and help you deal with future conflict with more grace. Don’t you want to be the kind of boss who forgives others?

Ask the Important Question: Would You Hire Yourself Or Fire yourself?

There’s nothing more soul scaring than staring into a mirror with the sole intent of being honest with yourself. We’re unique, we can be our own best friend and our own worst enemy. We’re essentially our own Dr. Jekyll and Mr. Hyde. In my opinion, being your own boss can be boiled down to one hard question. Would you hire yourself or fire yourself? It’s that easy, and it’s that numbing. If you can honestly look in a mirror and say I’d hire me because I do what I need to do, you’re on the right path. If you look in the mirror and say I wouldn’t hire myself, then you may want to reevaluate your priorities if your goal is to be your own boss.

Final Thoughts

Being your own boss is a mental shift. You’re no longer an employee, you’re calling the shots and since you are calling the shots you need to pay the price. If you can pay the price for success you’ll get there. If you can’t, you won’t. I only have one question for you. Are you mentally ready to hold yourself accountable and do the things required for success?

You be the judge.

Please like, comment, and tell me what you think. What do you think is the key for taking control?

23 thoughts on “How To Become Your Own Boss

  1. Be flexible – if the plan is to get your pirate ship to the secret island & a volcano blows up the island just as it comes into view – you don’t sink the ship because your goal is done blowed up 🙂 change happens so have plan b c d

  2. Lovely read. You have a grand gift for choosing subjects that we all think about and then writing about them with both humor and practical seriousness. I am more than a little envious 🙂

      1. On second thought, I am a whole lot envious. Every time I get an email that you’ve posted, I have three thoughts. First, oh, goody, something to read! Close behind it, Damn that TONYSBOLOGNA. He’s at it again. And, finally, Oh, God. I have got to get back to my blog.

        In my own defense, I have just finished–of all the things no one would imagine–a book for children about feral cats (for sale on Amazon, btw, all proceeds to a large feral cat sanctuary) and a real experiment, a 50 page novel “a sprawling family saga of three generations of a southern family.”

        That’s all. Carry on.

  3. Love this post! It’s honestly eye-opening. What you said about saying “I get to do this task” might actually be helpful in changing my perspective on a certain task. I will keep this in mind! Thanks for sharing! 🙂

  4. You da’ man. Excellent observations. I worked in Korporate Amerika for about 40 years and wonder how much different my life would be now if I had read this before I made that start. And was able to honestly step up to trust myself that much. Good read, bro.

  5. Introspection can be hard, especially when you have to not only admit to having warts, but commit to do something about it. It’s amazing how many people break promises to themselves (and how easy it is to do.)
    The more we operate in a gig economy, the more we need to get a handle on ourselves. Darn good advice, Tony!

Leave a Reply