Are You Ready to Become Your Own Boss?

woman standing with arms crossed

Are you ready to become your own boss?

You have worked hard for 20, 30, or even 40 years.

You have mastered just about everything there is to know about selling wine & spirits.

You have nothing left to prove except that you are not done yet. 

Not everyone is ready to retire. Perhaps this describes YOU.

But how do you know if you should keep searching for a steady paycheck OR take your knowledge, experience, and buyer contacts and go do your own thing? Are you ready to become your own boss? Here are six things to consider as you contemplate this:

1. You know what needs to be done and you do it.

man stretching at his desk
It’s certainly nice to be your own boss

It is certainly nice to be your own boss. Bosses typically tell you what they want you to do (or should do, or must do). But, this is the last thing YOU need. Imagine doing what YOU think should be done for a change. After all, you did not get to where you are by waiting around for instructions.

Have you ever brought a great idea to your boss and he/she said, “We tried that and it didn’t work?” Have you ever been told to just stubbornly and blindly move towards something you just knew would never work? Many of us have had experiences like this.

KNOWING what to do (and what not to do) comes naturally to someone who has spent 30 years doing it. The first sign that you are ready to become your own boss is you do not NEED a boss (and have not for some time now).


If you were to stop and think about all the times your boss held you back from doing something you knew was the right thing to, you would surely think hard about never allowing it again. There comes a time in every sales professional’s life when they realize they already possess everything they need to be wildly successful.

2. You have many things you value beyond money.

older man with his grand child
Money is no longer your top priority

Of course money is important and most of us still need it. But it is not the ONLY thing you need in your life. It is no longer your TOP priority. 

Many people in the wine & spirits industry talk about how they love what they do. They have a passion for the products that goes way beyond knowledge. They are able to see the bigger picture and relish the idea that what they do supports hundreds of people. Winemakers, cellar workers, vineyard workers, tasting room staff, all depend on someone SELLING the wines. Same goes for spirits, of course.


And you have other priorities besides work. It may be important to you to control your own schedule. You may desire the flexibility to be where you want to be when you need to be with the people who are important to you.

It is impossible to place a value of working only when you want with only people that you like selling only the products you love.

Many salespeople say they love being part of a team. They love seeing others succeed. 

The wine & spirits industry is no doubt the most competitive consumer product category in the world. Over 250,000 brands of wine alone fight for shelf space and wine menu placements.

Yes, competition is fierce! But, there is a camaraderie among competitors in our industry that few outsiders can comprehend. 

What if you could become your own boss AND be part of a team of like-minded people? Now THAT would be something special. Something many of us have only dreamed of. 

3. Stress? What’s stress?

business man
Working in Sales doesn’t have to be stressful

Working in sales can be stressful. Attempting to achieve your quota every year can be stressful. But, YOU have never truly felt it. You have consistently hit your goals and it has mostly seemed effortless. 

When you love what you do, you get very good at it. And when you are good at something AND enjoy doing it, the stress just does not touch you. Stress? Bring it on!

You have learned that the best way to beat stress is to excel at whatever you do.

Being your own boss has a different kind of stress, many say, but you are not worried. It would take a LOT to knock you down. You have seen it all. 

One of the best things about getting older, is your perspective changes. The things that used to keep you awake at night no longer seem to matter. 

4. You are just as driven as you have always been

Driven to work hard
Driven to work hard

They say “youth” is wasted on the young. This attitude pre-supposes only the young have energy and vitality. But, with age comes WISDOM and this wisdom tells us “drive” has nothing to do with age. 

Robert Mondavi was in his 50’s when he broke from the family business and started his own winery. Now THAT guy was driven! He worked like a madman. He out-worked everyone around him every day. 

If you stop and think about what drives YOU, you will see that youth has nothing to do with it. In fact, in many ways youth and inexperience is a hindrance. “Drive” in your mind means passion for what you do and for the products you sell. There is no expiration date on passion. In fact, passion takes on a patina that is far deeper the older you get. The brand of passion you possess is richer and deeper and more meaningful than it has ever been. 

You will know you are ready to become your own boss when you accept – truly accept – that youth can in no way keep up with a deep well of passion backed by experience. 

5. You believe in yourself

woman in business office
You can do it!

One of the great byproducts of believing in yourself and your own capabilities is you no longer let others’ opinions of you determine what you do and how you do it. 

Energy spent trying to “please the boss” dissipates as you get older and more experienced. 

At a certain point in your working life, you come to realize that you do not need to prove yourself to anyone but, well, yourself. 

Unfortunately, many people LOSE confidence in themselves as they age. Maybe you know someone like this. But, not you. If anything you feel like you are at the peak of your confidence. 

“Just tell me what needs to be done and get out of my way and let me do it.” Do you ever say this to yourself? You are not alone, by any means.

If YOUR self confidence is at its zenith, you are probably ready to become your own boss. 

6. You want to leave a legacy

Shaking hands
Leave your own legacy

Remember the apprenticeship period when people had to work unpaid for years before they earned their freedom to strike out on their own? In exchange for their freedom, the worker acquired valuable skills they could rely on for the rest of their lives.

The apprenticeship era was a good thing in many ways. Mostly because IT WORKED! Teaching, learning, and building. It was a great system.

Opportunities still exist to train up the next generation of wine & spirits professionals. We just use different terminology such as “mentorship.” YOU (yes, talking to YOU here) have a LOT to contribute to this legacy building. 

Your skills, experience, knowledge, and wisdom have great value! How great would it be to be able to pass it on? 

Many of you reading this post are entering into the “last chapter” of your working lives. Hopefully, it will become the richest and most satisfying one for you. Lord knows you have earned it.

You have had mentors, no doubt. If asked to talk about a few of them your heart would swell up and your throat would dry out.

Right now, there are younger wine & spirits professionals at the beginning of their careers. They yearn desperately for a mentor. If this strikes a chord with you, the best way to position yourself for the maximum contribution is to be your own boss. A boss with something incredibly valuable to pass on. It is extremely difficult to be a strong and caring mentor when you are stuck in the belly of the corporate slave ship pulling on a single oar.

The vast majority of people in the wine & spirits industry remain stuck in a job they do not like working for a boss they cannot respect. 

They do it because the thought of becoming their own boss is too daunting and risky. For many, it is downright scary. But, it does not have to be. 

If you are ready, we can help

woman on Ipad
Interested in being your own boss?!

A safer, more comfortable way to transition is to “plug in” to an existing framework where a great portfolio of wine & spirits await a great sales pro to sell them. You have the connections and experience. The framework provides the brands, the accounting, and the opportunities. 

Does such a framework truly exist? Indeed it does. In fact you are on their website right now as you read this.

We invite you to start exploring Green Glass Global by reading the stories of a dozen or so wine & spirits professionals who have already made the leap.

And if you want to speak to someone personally about YOUR particular situation, simply click here to speak to Bob McLachlan

Bob has been where you are. And he knows how to guide you to the next chapter which by now you have guessed is becoming your OWN boss!

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