What To Do When Your Business Mistake Leads To Financial Hardship

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One of the best things that ever happened to Scott Oldford was slipping into $725,000 of debt.

This may sound strange, but after interviewing him for my latest book (and getting to know him better since), this period marked a transformation unlike any other in him. It forced him to reevaluate his outlook on life, money, and business.

It ignited a new path, because what else can you do when you’re nearly $1 million in debt. There’s a reason you ended up there. You can’t have it all figured out, so the only solution is to seek a new one.

Scott isn’t the only person to go through this financial hardship turned life-changing epiphany.

Dan Miller told me about the time he lost his business and owed the IRS a ton of money.

Chris Brogan talked about wasting hundreds-of-thousands-of-dollars over the course of a few months, all because he lost track of the impact he wanted to create with his business.

I interviewed 163 for ‘The Successful Mistake’, although not all of them lost a life-changing sum of cash, many of them did. They all made mistakes. They all made decisions that affected their personal and business finances.

Chances are you have, too.

And chances are, you will make more of them in the future.

When you do, try this…


When Financial Hardship Hits, Do This…

Mistakes hurt. Failure stings. Hardship hits your ego. You ‘feel’ it, and nothing you can do will change this.

You cannot wake up one day and say “I will no longer make a mistake.”

It doesn’t work like that, but you know that already.

And I’m afraid to say, some of these mistakes will unravel and lead you down horrendous rabbit holes. They may start small, seemingly insignificant, but grow and grow until you wake up one day and realise you’re $725,000 in debt.

This didn’t just happen to Scott. He didn’t wake up one morning with a large cash-shaped hole in his floor. It occurred due to one decision after another, and before long he stood staring at a great void.

The same can be said for Chris and Dan, and the same can be said for you.

Mistakes happen, and whether you are the one who makes it or someone else does, it’s your mistake to fix. And when this mistake involves a lot of lost money, it’s hard.

It’s daunting.


If you notice a theme with Scott, Chris, and Dan, it’s that they are all successful people living happy, fulfilled lives today. They own great businesses. They impact a lot of people. They have purpose, and they provide meaning.

Not everyone who slips into debt gets to say this, of course.

Some lose their families, homes, and so much more. Some lose ‘themselves’.

But those who do not, tend to escape their financial pain by doing this one simple (yet all-important) something: they ask themselves how they got there. And more important, they ask themselves where they are going.

When you make a mistake that leads to financial hardship (for your business, your personal self, or even for your employer), it happened for a reason. You are where you are because of the decisions you make.

When someone else makes a mistake that affects you and leads to financial hardship, it happened for a reason. It’s your job to lead them. It’s your job to take responsibility.

It’s your job to ask how you got there, and where you are going next.


The Definition of Insanity…

They say the definition of insanity is to keep doing the same thing, but expect a different result.

The thing is, this is what most of us do.

We go through life doing the same things, making the same decisions, and reacting in the same way.

When hardship hits (financial or not), we react, ‘feel’, and do what we do — expecting things to work out. Sometimes we blame others. Sometimes we blame ourselves. Sometimes we shout and kick and scream. Sometimes this is what you have to do.

But when you’re finished, the only thing you can and should do is to ask yourself: How did I get here? Where am I going next?

When someone takes a whole host of money from you, it’s your opportunity to shine; get it back; build something better; prove who you really are; and leave an even greater splash.

Is this easy? Heck no.

It’s the hardest of the hard, but if you wish to be a successful leader and person, this is your only solution.

So although I hope you never get into debt like Scott, Dan, and Chris, I do hope you get to experience a period that motivates you to take what you do to the next level. You don’t need financial hardship to make this happen, but this is often what’s needed to force a person’s hand.

Whether it happens or not, now is as good of a time as ever to ask: How did I get here? Where am I going next?

Once you ask these questions and search for the answer, you can take your leadership (and everything else) to the next level.

Matthew Turner helps millennial entrepreneurs align their business + mindset so they build a legacy that changes the world. To discover how, visit: Turndog.co