My first-ever business was a smashing success, which is almost unheard of.

It was pure dumb luck... a good business idea with epic timing and the right team to pull it off. But also, at age 19, I was completely naïve and just convinced it would work.

That unrealistic optimism worked to my advantage. I didn't know any better, and failure wasn't an option- so I simply committed and ground away at the cliff face until I hit gold.

Sure it was hard, but I was completely unwilling to give up- and that mattered.

Four years later, I sold my business and stoked by my success, I dove straight into my second business venture... which failed horribly.

In my second effort, we were way too early to market. We were trying to sell something that no one knew they needed... and a lot of people couldn't even access. If we'd waited 5 or 10 years, I'd probably be a billionaire... but our timing was way off.

Lesson learned. On to business #3... which just barely broke even.

Sheesh, success is harder than I thought.

My fourth business, a technology consulting firm, did quite well and is still running steadily.

My fifth, sixth, and seventh businesses... all lost money.

And so on.

Here's what I've learned.

Five Rules of Success

#1 - Know your goal

Before anything, figure out as specifically as you can, what your goal is.

Let's suppose you have this goal...

"I want to start a home baking business."

There are a lot of reasons that dream might be important to you, and knowing why is very important to you achieving success.

You'd need to ask yourself, "what's my goal?"

• Is it to start a baking company, or is it to work for myself?
• Is it to work for myself, or is it to be financially free?
• Is it to be financially free, or is it to have freedom in my working hours?
• Or is my goal to work from home?
• Or am I trying to spend more time with my family?

Each of those goals might overlap in different ways, but knowing specifically what you're aiming for gives you far more options in how you get there.

Ultimately your goal might have nothing to do with baking at all.

#2 - If it's worth doing, it's worth committing 100%

What does it mean to commit?

It means that you never give up on your goal. You can change your path to it, your mode of transport, even your timeline- but you hold on to that goal.

Every time you hit a dead end, you change direction.

Every time you run into a wall, you climb it, or break through it, or find a way around it.

Every time.

Your goal itself might even change slightly as you move towards it, and see your core values more clearly.

But there is never a point where you give up.

#3 - Failure is only the beginning

"If you never know failure, you will never know success."
- Sugar Ray Leonard

In the Startup Playbook, author David Kidder interviewed Sara Blakely, the founder of Spanx. She credits her success to a key mindset her dad instilled in her.

He asked her every day, "What did you fail at today?" When she answered "nothing," he was genuinely disappointed, and viewed it as a day wasted. He made it clear that failure was an indication that she tried something new, and learned something new- and that both were essential to eventual success in life.

We think of failure as a disgrace, as a sign we've over-reached, or weren't enough.

That perspective is a very unhelpful to you creating the life you want. A far more helpful frame is to see failure as a simple process of trying, and learning.

Expect failure. Learn its lessons. Adjust your plan.

And then try again.

#4 - There is no finish line

I've been to the top of the mountain.

It was a hard climb, but yes it was worth it. I've seen the sunrise, and it's spectacular.

But here's the thing, once you're there, you discover a few surprises...

The experience is never what you imagined

I enjoyed my successes... a lot.

But they didn't give me what I thought they would...

I expected I would find happiness, contentment, and a feeling of self-worth. I expected to achieve permanent, lifelong, guaranteed financial security forever.

I expected I would have The Perfect Life.

But I did not find those things at the top of my mountain.

It's important to know, and to manage your own expectations. If you grew up believing in the "American dream," challenge that hard. Your imagination is easily tricked, in the same way that we fall in love with someone, and later discover that in reality, even the best relationship will have challenges.

Your life will never be problem-free, and that's just fine...

Pursue better problems, instead.

Keeping success isn't guaranteed

Your first challenge is to become successful.
Your second challenge is to keep it.

Did you think success was permanent?

Did you think that once you win, you take home the trophy, and retire?

Think again. That's not reality.

I found that the top of the mountain is often a very tenuous place. Yes you can sometimes rest a little bit, but just staying there is often just as hard as the climb itself.

Don't assume you'll get to relax... the finish line was a mirage and you'll need to keep on running. Be prepared for that reality.

You will likely be a bit disappointed

“Victory doesn't taste as good as it smells.”

Have you ever had a meal that looked and smelled incredible, but tasted... just okay?

How did you feel about that?

Chances are that your hype and expectations of "success" in your career, or in relationships, or in any area of your life is similarly over-hyped.

Be prepared for that, and set your expectations realistically.

There are always taller mountains in the distance

I was also really surprised to notice that once I was at the top of my mountain, there were whole mountain ranges full of other mountains that were taller than mine.

There was more success to be found, in other places.

"You didn't come this far only to come this far."

Worse was the realization that in terms of my personal core values, I'd climbed the wrong mountain entirely, and my journey towards happiness and fulfillment in life began all over again.

Fortunately, even this was just another life lesson, and I learned a lot from it.

#5 - Success has its downsides

What's the cost of success?

I was deeply surprised to discover that there are actually quite a few downsides to success.

Stress didn't go away... it stayed and even increased at times. I had a lot more to lose, and a long way to fall.

But in my personal experience, most of the downsides were social ones.

• Social pressure increased. People around you often expect more from you, and rely on you more heavily. In the eyes of some, you're just strong and dependable. In the eyes of others... you owe them, somehow.

• Other people want what you have, and will befriend you, manipulate you, or outright steal from you, if allow them to. That doesn't mean everyone is an enemy, but keep your eyes wide open... you'll discover who your true friends are soon enough.

• Prepare for resentment. Not everyone will like you. Your success amplifies the low self-esteem and victim mindset of people around you. You must have cheated or done something wrong, to achieve what they have been unable to... you nasty evil person you.

• Your value of generosity now has to be managed. You like giving and helping people? That's great... but what happens when people grab all they can and expect more?

• Fame is fun... to a point. Beyond that point, it's a burden. Ask any Hollywood superstar how many would give to just be able to go somewhere and be unnoticed? No paparazzi. No screaming fans. No one asking them for anything. Just peace.

This last statement might sound a bit abstract, but when you reach the top of your own mountain, I think it will make good sense.

There are fewer roses at the top of the mountain... but that makes them more special.

Final thoughts

It's interesting to look back on the many successes and failures of my life, and realize that at the end of the day, they're not so different.

There were certainly experiences and situations that I enjoyed, as well as ones I'd rather never repeat. But at the end of the day, all of these experiences helped me grow and change in positive ways.

Those experiences have shaped me into who I am.

More than anything, that's what I'm appreciating about my life journey so far.