How to Restart as an Entrepreneur After a Big Failure (or False Start)

By Sean Ogle •  Updated: 10/19/23 •  9 min read

One of the hardest things to do as an entrepreneur is to restart after a failed venture.  I’m going to let you in on a little secret that I haven’t told many people.

When I first launched my first course, Overcoming the Fear of Uncertainty, it didn’t go as well as I’d hoped.

While I received a lot of positive feedback from the people who did join and actually went through the course – the issue was that not that many people joined and went through the course!

It was my first information product, and was released long before I’d ever even considered using the word “marketer” to describe myself in any way shape or form.

I made a lot of mistakes with that first product.  Some of the biggest ones being:

So while it was (and is) a good program, the marketing around it was terrible, and ultimately led to the product being a bit of a failure during its first year.

How to Restart as an Entrepreneur: Pick Yourself Back Up

It can be pretty demoralizing when something you spent months working on and had such high expectations for, didn’t quite get where you wanted it to be.

However, it’s how you move forward and recover from that, that really matters.

Every single entrepreneur has failures and setbacks – that’s how you learn what works and what doesn’t.

We’re going to use my failure with Overcome Uncertainty and subsequent success with Location Rebel Academy to look at exactly how to restart after a big failure, or just as importantly, a false start.

It can be really easy to get super-excited about a new entrepreneurial venture, only to have it go nowhere.  If you’re going to reach your goal lifestyle and have that lifestyle business that allows you to do what you want, when you want, this post is going to be really important.

Assess your situation

When you’re trying to bounce back from a failure, you need to be brutally honest with yourself.  No more sugarcoating things to make yourself feel better – you need to be willing to drill down and rip your process apart in order to get to the root of the issue.

Here are the questions I ask myself every time I’m trying to regroup and learn form a past flop:

Answer these questions, and develop some tangible takeaways and things you could have done differently.

For instance, if the messaging wasn’t clear, decide what would have made it clearer, and be cognizant of this when working on your new project.

Review exactly what worked (and what didn’t) in previous ventures

When I was early in the planning stages for Location Rebel, this is exactly what I did. I assessed everything about the Overcoming Uncertainty launch and really focused first on the things I found to be the biggest issues.

In this case those were:

It’s important to remember that this assessment works regardless of whether it was a specific product/service that failed, or an entire business venture.

Maybe you tried to build a freelance writing business and things just never panned out for you. These same questions are all still relevant, and can make the difference between success and failure if you try and fire it up again.

Set realistic and measurable goals

Ok, so now you should have a pretty good idea of what went wrong with your last project.  But how do you ensure you get and stay on the right track when you restart?

You need to know what success looks like.

The problem with most goal setting is that people say things like “I want to be making $5k/month within a year.”

That’s a perfectly respectable goal, but there are two problems with it:

  1. While tangible, you can’t directly control your income. Goals that will lead to making the money will keep you from getting frustrated if you don’t get there. Cold call 50 new clients this week is a better goal.
  2. Without many smaller goals, you’ll never feel like you’re making progress.

Let’s talk about that second one a little bit more.

Starting a business is freaking hard. If all you have are big lofty, long-term goals you’ll never notice the incremental successes, and all of the little things that lead to long term success.

Outline the process you’re going to have to take to be successful, and set small goals all along the way:

Goals like that will remind you to celebrate the little wins, and will get you excited during every step, as opposed to making you feel like you’re stuck in the mud and not making any progress.

Make sure you’re offering something that others want (and know they want)

We mentioned this in the review sections above, but I want to take a minute and really highlight this concept, because in the end it’s probably the most important thing to keep in mind when starting a business.

If you can assess what people’s problems are, and offer them the solution they’re looking for – then you’ll never have trouble making money.

Before sinking days, weeks, and months into something make sure you’re going to be offering something that people know they want. 

Sounds easy enough, but how do you actually figure out what people want?

You talk to them.

I’ve seen advice all over the place about sending people a survey (and I’ve probably even given that advice in the past), but the reality is, the information you get is usually worthless.

When I did my first survey for Location Rebel Academy, I asked about price.  I said how much would you be willing to pay, and gave 4 options, the most being $250+.

Do you know how many people said they’d pay that?


Do you know how many people have paid more than that for access?


People don’t spend much time on surveys, and even if they did, it can be difficult to get useful information – regardless of how good your questions are.

So how do you get good, useful information about what they really want?

You ask them questions, and start conversations.

I try and start conversations with as many email subscribers and readers as I can, simply by asking them a question and asking them to respond to it.

I get often get much more valuable information from one of those conversations than I would a survey with dozens of responses.

Not to mention I’m building a relationship in the process which ultimately benefits both myself and the reader.

So here’s how you find out what people want:

  1. Ask people (readers, friends, other contacts, etc) what problems they’re facing right now. If you have a specific product or service in mind, ask him the same question as it relates to that topic directly.
  2. Compile responses in one place.
  3. Review and assess

Pretty simple, huh?

The more people you talk to and listen to, the more information you’re going to get that will help you build a business around a major pain point people have.


There’s one other very important piece to the startup puzzle: accountability.

Many people simply can’t hold themselves accountable, in fact, that’s probably one of the biggest reasons you failed to begin with.

So when you restart you have to find a way to hold yourself accountable.

Find a community of like-minded people and work together to ensure you’re reaching your goals.

Write a check to your significant other for $500 and put it on the fridge – if you don’t do everything you said, they get an extravagant gift.

Try a more condensed work schedule to keep you focused.

Whatever it is, think about what it’s going to take to find accountability and treat it as one of the most important parts of the process.

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Moving Forward

Starting a new business after a previous failure or false start can be an intimidating process. However, success lies from proper planning if you follow these steps, plan accordingly, and remember to celebrate the little wins all along the way, you’ll be successfully working on your own in no time!

Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
Learn How to Make Your First $1,000 Freelance Writing (in 30 Days or Less)

Join over 40,000 people who have taken our 6 part freelance writing course. Sign up below and let’s do this together.

By entering your email address you agree to receive emails from Location Rebel. We'll respect your privacy and you can unsubscribe at any time.

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8 comments on "How to Restart as an Entrepreneur After a Big Failure (or False Start)"

  1. Donnie Law says:

    It’s nice when entrepreneurs admit when their projects don’t go perfectly as planned.

    1. Ron says:

      Transparency is a most significant ally for web entrepreneurs. You immediately lend your trust to the writer because you sense the genuineness, because you too can relate to those very experiences.

  2. Martin says:

    I’ve read every article on the topic and even bought eBooks/courses on how to launch. The problem is that at the end of the day, you might just have a crappy audience.

    Sometimes you just have to give up and work on something else. The idea you’re working on just isn’t good.

    1. Sean says:

      Yeah this could be true, but at this post was trying to look at the broader scope of business. So if I launched, say Location 180 as a business, and it didnt work out for any number of reasons, perhaps you dont just create another product for the same audience, but you create a whole new brand or business instead.

      If I launched kitchy cell phone cases and it didnt sell, then I probably wont start that business again, I’ll try something else.

  3. Ana says:

    Hate to admit it, but I agree with Martin. If your idea just doesn’t hold water … well, by failing you just found out that it doesn’t hold water.

    That’s what scares me most. Not all the other steps, not even accountability which I’m still working on. It’s that my idea just may not be what people want. Your biggest trick is getting to the point where what you want is what other people want. Wow. Daunting, huh? It is for me. Now I’m back to looking for people to find out things from. Like, what specifically is their pain point. What do they want that I can provide?

    You did a real service for entrepreneurs, and behaved like a true entrepreneur in this piece. It’s one of those connecting-with-people things we take seriously. I know I do. Great job!

  4. Chas says:

    Honestly, I have failed with many different things and have fallen for a lot of scams. It can be disheartening and make one jaded. The internet is full of scams, and while some things may be legit, they won’t necessarily work for everyone. I am sitting on a new domain, but, have to admit that I haven’t done anything with it, as I feel like I’m in a rut, and have lost my sense of direction, as to where I want to go with it, and sometimes wonder if it’s worth the effort.

  5. Great article! I haven’t really failed (not yet) on anything so far, but it will defiantly happen. After reading this it is actually quite obvious what you should do, just that it hard to put your finger on it yourself.

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