5 Questions to Ask Yourself This Labor Day

It’s Labor Day, one of those holidays that we like to observe but are most likely working away or writing a blog post like this one.

Anyway, it’s Labor Day and it’s intended as a time to reflect.

This Labor Day is somewhat different for me as I’ve actually decided to take a real vacation.

I’ve had the joy over the last couple weeks saying no to clients, yes to day-time Netflix, and “why” to questions about what am I doing and what I want with my life, the later being the most transformational.

There are a lot of guru’s and self-help experts out there providing their equation for success or a life fulfilled, some of it quite valuable.

But I’ve found the most value both in my business, with myself, and with my clients by simply just asking myself a lot of questions.

Through this process, I’ve learned a lot about myself, the ego that brings me down, and the friends who make us who we are.

But more importantly, I’ve learned a lot about “work” and and wanted to share 5 questions that have helped transform my idea of what employment means and my place within it.

For those looking for a little direction this Labor Day, maybe you’ll discover that the answer to finding the direction you’ve been looking for lives in the questions you have yet to ask yourself.

Here are mine:

Who do I get the most joy out of serving?

Do have a specific feeling of fulfillment when you’re entertaining a crowd, pouring a draft beer, or delivering a presentation? If so, is there a certain audience you seem to resonate with more than most? I don’t think this is an accident, I think it’s a calling. By asking myself this question over the last year, I’ve learned a lot about the audiences that need the skills I’ve been endowed with along with the those who I know I can provide the most value to. Whether it’s generational or geographical, think about this for a second and it might give you some insights as to where the Universe is calling you next.

What’s the one thing you’ve been doing the last 5–10 years that hasn’t changed?

Recently, I started to partake in a field I was once an expert in about 12 years ago. I made a big move, reconnected with some of my favorite people in that space, and even won some big client work as a result. But I also realized that I hadn’t been working in that particular space for the last 12 years for a reason, I’m not sure internally I really liked it. As a good friend put it, the situation was similar to reconnecting with an old girlfriend who you realized you broke up with for a reason. On the flipside I decided to give myself permission to accept the fact that all the strategy work, startup building, and brand innovation I’ve been doing was something I really enjoyed and that it was okay to actually enjoy the ridiculous world of marketing and advertising.

Whom was the last person to reach out to you for help and why?

This was an interesting one and similar to question #1. I think that different things full-fill people in different ways, that’s what makes the world so colorful. What fulfills me is service to others. But there is a big difference between being of service to someone who needs your help and trying to help someone that already has enough suiters- you feeling me agency world? A similar principle is applied in market theory and opportunity. Great businesses are developed based on a need and necessity, not always just because someone thinks they can do it better, though this can be true too. In this situation, I recommend looking to see who is filling your inbox, text message threads, and more and see if there is a bigger need out there opening up as opposed to running into the same doors that keep closing.

If you had a billion dollars, what would you be doing tomorrow?

Easy right? But really, if you had all the money there was, what would you do? Make a movie, open up a cafe, or start a local bar? I like this question because the answer you’re looking for isn’t in the response but in the details that come with it.

For example, you might say you would quit your job in advertising and open up a craft brewery. Then I would say, “Then why don’t you?” And you would say things like, “It costs too much, I don’t have the experience, and I need the money I make from my advertising gig to cover all these bills.”

Then, I would say, “If you really wanted to do this, why not get a part time gig working nights or weekends at someone else’s craft brewery to learn the craft more, or go to a night school/class to study what it takes to be successful, or if everything is so expensive and that’s all that’s holding you back, then why not downsize your lifestyle to divert the costs to thing that will actually make you happy?”

I’m guessing an internal debate would then ensue, which leads us to our final and most important question.

What do you need to sacrifice to get there?

Sacrifice is something easy to read about, but just about impossible to practice. I don’t know you as well as I know myself. However, what I’ve learned is that true sacrifice (macro or micro) is what is usually standing between us and our true selves. After all, who wants to die to anything in a world that says you can have and be everything. But the truth is, you really can’t have your cake and eat it and that is a blessing in disguise.

Per the above, you’re not willing to make the appropriate changes needed because you’re afraid, and that’s okay.

You won’t downsize the giant house you don’t need and ridiculous mortgage because you’re afraid people (usually family) will think less of you somehow. You won’t stop drinking and focusing on your future because you’re afraid life without IPA’s just isn’t that exciting. And you’re afraid that going from a job as a finance executive to children’s book author is just plain ridiculous and not realistic.

And you know what, you’re right. Success and happiness in any of these things isn’t guaranteed, but working yourself to death for a paycheck you really don’t need (or internally want) doesn’t always bring happiness either, so why not do something that will at least bring you a smile?

As my favorite Jim Carrey quote says, “You can fail at what you don’t want, so you might as well take a chance on doing what you love.”

And that’s the simple, yet very complicated, truth.

The only person standing in your way however, is you. Can you get over yourself?

Maybe that’s the next question that should be on this list.