From Confused to Confident: What Trying (and Failing) to Start a Business Taught Me

Jun 03, 2025

Since I was a senior in high school, I've wanted to be in business for myself.

I didn't know what that looked like, how I was going to get there, and what it would cost me. At some point, many, many years ago, I officially formed an LLC. Despite the fact that I didn't have a product or service to sell, and I didn't have customers ready to buy.

For much of my twenties, I spent most of my time working dead-end jobs because I didn't know the fundamentals of starting a business.

Worse still, I didn't have the mindset to go out into the world and find out.

Towards the end, it started to feel like an important part of my being was missing. No regular old 9-5 was going to be able to give me what I desired.

I also held this inaccurate expectation as to what starting a business was supposed to look like. So, every attempt I made, I failed, or more accurately, I pivoted.

The first decade of my adult life was spent gaining skills and figuring out what I didn't like. If I did sales, I wanted it to be with products that I could stand behind and honestly promote because I believed in them. If I did customer service, I wanted it to be upscale despite the fact that that wouldn't shield me from customers having a terminally bad day.

I was lucky to find these qualities in some of the jobs I held in my twenties.

But as you might assume, it wasn't enough.

I was coming into my thirties, and believed there was no way I could settle for a job paying less than $20 an hour. I had big plans for my future, and I needed a job and business that could support them.

So I pivoted.

I didn't want to do dropshipping because finding a winning product is like playing the lottery. It also lacks control over the end product. White labeling was an option, but I still didn't own the product.

I pivoted again.

This time into services.

I cold emailed potential clients. I added and reached out to business owners who didn't have or needed an upgrade to their website on LinkedIn. And I hated it.

So much effort for so little result.

Plus, I didn't like that I had to reach a certain quota each month to survive.

So I pivoted again.

Writing.

This was about a year ago when I decided, the single most important thing I could do for myself is write. It's a skill that will never go out of style. Everyone needs words.

At first, I figured I could post (tweet) about the things that I've learned over thirty years of life. Help someone who is 2 or 3 steps behind me.

Help them avoid the trouble I encountered on my way to starting a business.

I found it starts with you--the business owner.

The vibe, culture, and values of the organization stem from your vibe, culture, and values. How you perform a task will inform how someone else will perform the task later.

What you believe is important, they will believe is important.

They are your future employees.

I pivoted again.

Yes. I know.

Still writing, but doing so because I enjoy the process. Not because I see the profits. A few months ago, I started teasing a Masterclass on Personal Development, something I wish I had ten years ago. A product I would be glad to sell because I believe in it and have lived it.

Meanwhile, I'm giving away some gems, or what I like to call the juice.

The essence of the things I think you need to live your most prosperous life.

Between all those pivots, I learned that you must have a vision, but only after trying a bunch of things. Tasting each ice cream flavor in the shop--picking two or three to focus on right now. One that makes you money. One that keeps you healthy. And maybe one that makes you more creative.

Give them six months to a year as your sole focus, and see what happens.

What will you learn?

Who will you become?

What will you create?

Here are three things I would keep top of mind if I were wanting to start a business and make some serious money.

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Without Vision, You Cannot Forge The Path Ahead

In the many things you dream of doing, you must have a vision.

Something to hold on to when things get tough because they will get tough. You will be tested. Your business will be tested. These are the moments where it is crucial to have vision. A means of pointing the ship in the right direction.

Starting, I lacked vision.

I didn't know what I wanted. Really.

Then all of a sudden, I'm in my thirties, and it all starts to become clear. That the things holding me back don't matter. What matters is continuing to take a chance on myself and my ideas.

You have to believe in yourself and your vision.

For me, I want the ability to do what I want, when I want, with whom I want, where I want, on my dime. I don't want to have to rely on anyone for coin. Yet, by creating daily, I'm constantly creating opportunities for cash flow.

I know to get there, it's going to take years, not months.

Stick to the vision, which will evolve as you do.

It Doesn't Matter What You Do, Do It With Your Whole Chest

The problem with most wanapreneurs is that they spend more time crafting the perfect business plan instead of testing and validating ideas.

There are hundreds of thousands of ways (if not more) for you to make money online.

Neither is better than the other.

What matters is how well you know yourself to find your way, while using the lessons others have learned as test cases for your use.

If someone else is making money in what you love to do, sure bet you'll do just as well with the right amount of effort and maneuvering. If someone else isn't doing what you want to do, you get to pave that path. So experiment often and get feedback fast.

Otherwise, it doesn't matter what you do.

Do it with everything that is in you.

Even if that looks like a 10% after a 90% day. Showing up is the important thing. Second to doing it as frequently as possible.

When You Have Money Coming In From Your Business, File For Your LLC

There's no magic figure I could give you for the point when it makes sense to form an LLC.

For me personally, I'm waiting until I've made my $25,000th dollar in a single year. Then I would look for grants to fund my business to the next level.

Filing for an LLC in your state may or may not be expensive.

I know it is way cheaper to start an LLC in Florida than in Nevada. Makes me think I should have cash on hand to keep current with my business license.

The money you would spend otherwise might be better suited to something that can get you as close to a sale as possible. Don't be desperate about it, but rather logical.

If you need the juice on this, I highly recommend picking up a copy of Million Dollar Weekend: The Surprisingly Simple Way to Launch a 7-Figure Business in 48 Hours.

Quick Recap: Starting A Business

1) Without Vision, You Cannot Forge The Path Ahead

2) It Doesn't Matter What You Do, Do It With Your Whole Chest

3) When You Have Money Coming In From Your Business, File For Your LLC

Solve your own problems, and sell the solution.

Think of a process or action you took to resolve an everyday problem.

What comes to mind? Drop it in the comments.

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