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4 Steps To Overcome Life’s Biggest Obstacles As An Entrepreneur

I’m an entrepreneur. I rely on my wits and keen business insight to sniff out opportunities and go after them.

It’s wired in me and I don’t think I could ever be as happy working at a regular 9–5 job. It’s just not my cup of tea – I’m sure you can relate.

For me, entrepreneurship was and still is an exciting journey – a roller-coaster ride of a lifetime – and I have yet to regret taking that route. But to say it’s riddled with obstacles and lined with dangers would be an understatement of the century.

Our personal, social, and professional lives keep throwing us curve balls all the time. It’s something you learn to deal with. But I’m pretty certain entrepreneurs have a lot more to deal with than your average Joe who works at a law firm. Usually, he can sleep peacefully knowing that his job is waiting for him when he gets up in the morning.

Now, don’t get me wrong – our economy is in shambles and no one can really rest easily right now. But solo entrepreneurs are juggling five pins any given day – and we’d all love to be able to put one aside from time to time, just to catch our breath.

Three Major Obstacles on Your Way to Success as an Entrepreneur

Being an entrepreneur for such a long time I came to realize that all the troubles that plague me, and my colleagues, can be filled under three broad categories:

  • Health problems 

  • Family problems

  • Money problems

Each on their own is terrible enough to deal with but sometimes they join forces and kick you in the teeth so hard that you’re sent reeling backward.

Most entrepreneurs grind themselves to death by constantly working, worrying, and stressing out. Bills to pay, mouths to feed, business to run – it puts a lot of pressure on a person.

So your health starts deteriorating

And if you get hit by a debilitating illness at the same time then it’s only natural to think it’s time to close the shop and call it quits. Luckily for me, I’m a relatively healthy guy and other than stressing out too much I don’t have any health issues worth mentioning. But the point is; you never know when something shitty in this department might come your way – it’s a gamble.

Family and money issues seem so self-evident for me that they came to me as an afterthought. Of course you’ll have family problems – you’ve dubbed your job as your passion so many times that you don’t even notice it anymore. When was the last time you told your partner that they were your passion? Or your children for that matter? It’s ridiculous how many entrepreneurs end up divorced – statistics show that this number goes up every single year.

There is simply too much strain put on both partners for everything to function normally, especially when you lose sight of the bigger picture and just start going through the motions.

See how the little pieces start to fit in to paint a very ugly picture?

And to top it all off, you have money problems. When things start to go bad for an entrepreneur it’s a downward spiral. Most entrepreneurs are either a sole proprietorship or an LLC. In both cases, you’re screwed and can be left with nothing if things go south.

In the first case, creditors can get everything you own. In the second, the banks can – I’m pretty sure you’ve pledge your own assets as collateral when you were getting that loan. This means that your house, your car, your boat – your everything – can go up in smokes in an instant!

Been there, done that. 15 years ago I was married – happily, unhappily, it doesn’t really matter anymore. Somewhere along the way my wife and I drifted apart and filed for divorce.

The divorce left me in shambles, both emotionally and financially. I was drained and felt as if life has gotten the better of me. I also lost 95% of my assets and came very, very close to personal-bankruptcy filing.

It was a horrible period of my life and I wallowed in it for a while, I have to admit. But then something clicked. I decided to stop being a victim. That whole ordeal put a new fire in me and I realized I was neither better off nor worse off than I was when I started my first business.

So I dusted myself off and gave it another go.

The Time to Overcome

It took me quite some time to become the man I once was but I was determined to do it. In retrospect, I came to realize that I did follow certain steps towards recovery that I’d like to share with you now.

1. Lose the negativity in your life and surround yourself with driven people

This is a biggie. I couldn’t really get to where I wanted to go because people were telling me that I’m in it deep over my head. My lawyer was urging me to file for bankruptcy and so was my family – hell, even some of my friends were siding with them.

But the thing is; I’m not a quitter and I’m sure you’re not one either. So I took a step back, I removed myself from all the negativity that surrounded me and got in with people who had their sights firmly on the goal, no matter what.

Of course, I didn’t ditch my friends entirely – they were only trying to help me. But I realized that they were pulling me down – they were panicking more than I did and I needed focus. One person in particular helped me out and that was my friend Seth. He was going through the same deal I was but he had a clear-cut vision of where he wanted to go and there was no stopping him! It was truly inspirational.

2. Own your mistakes and make a plan

For a while, I blamed everyone for my personal and professional problems. It was my wife’s fault that we ended up divorcing and, of course, the marketplace was to blame that my business was in a slump.

One day, Seth pointed out that those who do not study history are doomed to repeat it. So I sat down and took a cold, hard look at my life up to that point – all the decisions that I made that influenced both my personal and professional life – and I realized I have no one to blame but myself.

I urge you to do the same thing. If you’re ever in a bad place, look back and identify your decisions that landed you there. Make a solid plan for moving forward, making sure to identify the pitfalls you’ve encountered earlier and ways to get around them and start marching.

Now is the time to put all those worries behind and focus on the road ahead – and that’s what I did. I threw myself into a new venture, planned it all out to the smallest details – well, as much as I could, of course – and held my gaze firmly planted on my goal, owning and running a successful Internet Marketing enterprise that I will eventually grow into major player in the niche.

And guess what? That is exactly what I did!

3. Turn inwards

As I mentioned, surrounding yourself with positive, driven people is essential. They will help you anchor yourself and give you that positive energy you need to push forward.

However, neglecting to let things go will hurt you in the long run. I carried a lot of resentment towards myself in the years after my divorce. From blaming my ex-wife I turned to blaming myself.

Then I took up meditation. I learned how to spend time with myself and my own thoughts, how to accept them and how to dismiss them after I owned them. If you fail to do this you will lose confidence in yourself and your abilities – no entrepreneur wants that happening.

Meditation coupled with spirituality did it for me but you don’t even have to be spiritual in a real sense of the word. You just have to be comfortable enough with yourself to understand that every aspect of your being makes a whole – some aspects are good and some less so but all of them make up what you are. Contemplate in solitude and you will learn to appreciate the finer points of your being and accept and change those that need a bit of work.

4. All things are fleeting…

…and you would be wise to remember that. I’m in a good place right now but I’ve learned to accept that tomorrow I might not be.

Life is funny that way – when things are going great people get blindsided and topple over at the slightest sign of trouble coming their way.

Never plan for failure but understand that eventually it does visit your neck of the woods. You have to put up a good fight and if it doesn’t work, dust yourself off and try again. Rinse and repeat, so to speak.

There will always be things in your way, whatever the goal you set for yourself.

The universe rarely conspires to make your life easier.It most certainly didn’t in my case. And it didn’t in the cases of Henry Ford, Milton Hershey, Larry King, or Francis Ford Coppola – all people that filed for bankruptcy at one point but whose estates or personal wealth are now valued at tens, or even hundreds of millions of dollars!

True success is measured in how you handle your failures.

Do you fold? Or do you buckle down and persist?

I persisted!

And I hope you will too!

Much love,



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