Entrepreneurs: Find Your Purpose with 17 Questions

[NOTE: This is the second in a series of posts exploring the topic of entrepreneurship. While my focus has and will continue to be on Facebook ads, I have plenty to share about what I’ve learned while building my business.]

More than five years ago, my entrepreneurial journey began — whether I knew it or not — when I was laid off for the second time in two years. I didn’t immediately know that I was starting a business. As a result, I didn’t have a plan. I winged it.

My direction has morphed multiple times since that fateful first day. But the greatest amount of change occurred during the first year when I was rapidly discovering my purpose.

I didn’t go through the following exercise all at once. As I said, I was figuring things out on the fly. But looking back, these are ultimately the important questions I needed to ask myself to determine which path to take.

If you’re stuck and unsure of where to start with a new business — or where to take a struggling one — begin here. This brainstorming exercise won’t give you a plan. But it will help clarify the priorities that mold that plan.

Some of this may seem too deep — too personal. You may ask yourself how it has anything to do with starting a business. But ultimately, all of this is connected.

We need to help you find a path that is permanent and sustaining. Something that allows you to tap into your passions, leverage your strengths, avoid what you dislike, and provide lifelong fulfillment.

This is just the beginning. Next week, we’ll take the next steps.

It’s time to get honest with yourself. Find a quiet place. Set aside some time. Let’s begin…

1. What Am I Good At?

You aren’t perfect. But you have strengths. There are things that come easily — or more easily — for you. What are they?

We’re brainstorming. Try not to spend too much time on each answer. Attempt to create a list of 5-10 primary strengths.

To provide an example and show that I have skin in the game, too, I’ll try a few of my own…

– Writing
– Teaching
– Coaching
– Parenting
– Problem Solving
– Big Picture Thinking

If it’s easy to list 10, 20 or more strengths, go for it!

2. What Are My Weaknesses?

Be kind to yourself here. The truth is we’re not good at anything without experience. So this list could easily be long. But don’t allow it to be any longer than your list of strengths.

Mostly, these should be things that you struggle with on a daily or regular basis. Things that you are working on — or maybe things that are a lost cause.

Here are a few of my weaknesses:

– Procrastination
– Public Speaking
– Verbal Communication of Love and Appreciation
– Organization
– Completing Tasks
– Details
– Impatience

We don’t need to obsess over each weakness and provide details. You know what they mean. Focus on assembling a complete list.

3. What Am I Knowledgeable About?

This could be related to your strengths, but it doesn’t need to be. Here, we’re focused more on subject matter. What types of useful and useless information clutters your brain?

My short list:

– Baseball
– Facebook Marketing
– Music
– Sports
– Technology

These are things that interest you. You have experience here. Maybe people come to you when they need information about the topic.

4. What Do I Love to Do?

There could be crossover here between what you’re knowledgeable about, what you’re good at and what you love to do. These could be business related, but they don’t need to be.

A few of my examples:

– Coach baseball
– Watch my sons play baseball
– Watch football
– Watch movies with my wife
– Travel with my family
– Sleep

Yep, I love sleep!

5. What Do I Like to Do?

Take a step back. The things above are the priority activities in your life. But let’s go down a level.

Here are some of mine:

– Run
– Solve problems
– Eat
– Listen to music
– Write

6. What Do I Hate Doing?

What situations and responsibilities repulse you? What makes you feel least comfortable?

My list:

– Clean messes
– Travel by myself
– Sell
– Cold call
– Argue
– Drive through traffic

Yep, I’m a marketer who hates to sell. I learned that in one of my first jobs where I worked as a telemarketer. And of course, that’s also why I can’t stand cold calling.

7. What Are My Unfair Advantages?

It’s important that you’re self-aware. You understand that you may have some built-in unfair advantages.

This doesn’t mean you don’t earn what you get. This doesn’t mean you didn’t work hard. It just means that you have certain advantages right now that not everyone has.

I’m fully aware of mine. Here are a few:

– Education
– Upbringing
– Social status
– Neighborhood
– Connections
– National Basketball Association

I feel very lucky. I can’t help but acknowledge that many of these unfair advantages were important to my ultimate entrepreneurial success. Know what these advantages are so that you can take advantage of them.

8. What Are My Assets?

These are the things or people around you that may help you during your journey.


– Home office
– My wife
– John Robinson
– Connections
– Experience

I have a workspace, a supportive spouse, an entrepreneurial cousin who can help guide me and many connections from prior jobs. These assets gave me a leg up.

9. What Do I Value?

We start getting more personal now, but don’t skip ahead. These things are important. We will ultimately need to go on a path that allows you to embrace what you value.

These could be things, people, personality traits or anything that matters to you.

Here we go…

– Family
– Honesty
– Transparency
– Knowledge
– Time

These five things certainly frame what I do — and what I’m unwilling to do.

10. What Do I Despise?

It’s important that you’re clear about things that repel you. Ultimately, your direction needs to steer clear of these things.

Things that I stay away from:

– Greed
– Hate
– Bravado
– Selfishness
– Ignorance
– Politics
– Arguments

Knowing what you don’t want to be is as important as knowing what you want to be.

11. Whom Can I Help?

Now we start approaching business-related possibilities. Based on your knowledge, what you’re good at, and what you love to do, who can benefit from your experiences?

A few of mine:

– Baseball coaches
– Baseball parents
– Entrepreneurs
– Marketers
– Consultants

You don’t need a business idea in mind for any of these. Just recognize what groups of people could use your help.

12. What Problems Do They Have?

Now create a list for each group, putting yourself in their shoes. Think about the problems they are facing and the questions they may be asking.

Below is my example for marketers:

– Targeting properly
– Putting together a strategy or plan
– Understanding all of their options (overwhelm)
– Simplifying
– Achieving a positive ROI

13. What Makes Me Happy?

There doesn’t need to be a direct relationship with business when creating this list. But know this: Whatever you do in life, it must allow you the ability to experience these things that make you happy. If it takes you away from them, it isn’t worthwhile.

A few of my “happy places”:

– Making a difference
– Sitting in the stands at a baseball game
– Achievement and overcoming obstacles
– A smile on my sons’ faces
– Comedy

14. What is My “Big Why?”

This is your story. Your purpose. The meaning behind what drives you.

In 2003, our oldest son Michael was diagnosed with Neuroblastoma, a rare form of childhood cancer. That period of time helped me appreciate what was important, prioritize my life, and ignore what doesn’t matter. Michael is a healthy teenager today, but that experience forever changed our family. I appreciate time: Time with my sons, time with my wife, time that I’m alive.

My “Big Why” is my family. My motivation is to provide for them, and — more importantly — spend time with them. Providing for my family without creating time that can be shared is counterproductive. I ultimately want to look back at a lifetime of experiences — not wasted hours spent on and endless desire to “achieve” and profit.

15. What Lifestyle Do I Desire?

When you’ve reached the peak of your profession, what does it look like? What does it allow you to do? What type of life would you like to lead?

Here is mine:

– Flexible schedule
– Travel with family
– Evenings, weekends and holidays free of work
– Financial freedom — without excess or dependence
– Quasi-minimalist

This is your goal. Whatever you do, it’s to reach this lifestyle that makes you happy.

16. How Important is Money?

This question is important. Don’t sugarcoat your answer. Be honest.

Your answer needs to be consistent with your purpose. If you determine that money is important, but your goal is to help those less fortunate, you are having a match-up problem.

Where on this spectrum are you?

1 – No importance
2 – Minimal importance
3 – Some importance
4 – Very important
5 – Primary focus

For me, money does have some importance. My wife and I have three sons. I want her to remain free of a job so that she can follow her passion of being active in their schools. We have lots of bills to pay, baseball teams to fund and college tuition to plan for.

Additionally, I do like nice things. Not extravagant things. Not completely unnecessary things. But nice things. And if I want to travel with my family, that isn’t cheap either.

As a result, I’d put the importance of money, for me, somewhere between 3 and 4.

17. How Important is Fame?

Where on this spectrum are you?

1 – No importance
2 – Minimal importance
3 – Some importance
4 – Very important
5 – Primary focus

I fall at a 1 here. I have no desire for fame and the problems that accompany it. I don’t want to be on your TV screen or trending on social media. I cherish a level of privacy.

Of course, that is somewhat at odds with what I do. I have a brand based on my name and I don’t hide behind a logo. But as my business grows, I will need to make a decision: Does growth consist of becoming more “known”? Or is it something else?

I plan to pull my public self out of the business more and more in the coming years. I already began that transition — a pullback on my initial direction — a year ago.

But maybe fame is something you desire. If so, be honest with yourself about this early. Being public will need to be a priority.

More to Come

As mentioned at the top, I am taking a risk by venturing away — even briefly — from my focus of Facebook advertising. Consider it an experiment. While I do see great potential here, I first want to be sure that it’s a topic that interests you.