5 Questions To Ask Whenever You Feel Like Giving Up

5 Questions To Ask Whenever You Feel Like Giving Up

The hardest decision you’ll ever make is to move on; before you do answer these 5 questions.

As entrepreneurs we believe in our ability to build the future more than anyone else possibly could. In our mind there is never any doubt that what we are creating is needed by the world. That’s why we will risk our fortunes, homes, even our relationships to achieve our goals. I’ve been there, done that, many times.

And along with the success it brings I’ve also visited the dark side of entrepreneurship; that point where a venture is on the precarious precipice of failure. When you’re standing there, looking at the abyss ahead, it’s pretty hard to adopt a rational perspective and make a well-informed decision; but there are a few questions to ask yourself that might alter your perspective just enough to help you decide on the next step.

1- Ask yourself if you are giving up on or transforming your vision?

My first business was a software company with an app that converted complex code from one programming language to another. It was an absolute masterpiece. However, clients still wanted us to manually convert their code. It made no sense. Our app converted code perfectly and only cost $10,000. Manual conversion added at least another $100,000.

We soon realized that the real money wasn’t in the software but the services. “Giving up” on that software app was the inception of Delphi; a rocket ship we rode for nearly 20 years.

“What may seem like giving up may be your greatest opportunity to change direction and find the real mother load.”

It’s easy to get lost in your original vision, but few original visions are what ultimately propel a startup into orbit. They are usually more like the blasting caps that ignite the dynamite. What may seem like giving up may be your greatest opportunity to change direction and find the real mother load.

2 – Is the box you’re in the one you want to be in?

I hate the phrase “getting outside of the box.” Every business is inside a box measured by profitability, customer satisfaction, growth, and value. Rather than just get out of the box, how about making sure you’re in the right one to begin with. Look carefully at what you’ve built. What parts of it make sense, what parts don’t? It’s often the case that there is still a great business if you can just focus on the parts that work. Reengineer and amplify those pieces that do work and cut lose the rest. That’s not giving up; it’s evolving–and it’s often that easy.

3 – What about your team?

It may be your call but you’ve also got a team that is invested in this dream. What are their attitudes and ambitions? Where do they see the value? Where are their hearts and minds? You may be ready to give up but you might be surprised by the staying power of your team. Have a transparent conversation about options. In my experience I’ve found that trust is earned most in situations where the hardest decisions need to be made and people are given a voice in helping to make them.

4 – How long is your runway?

Be honest with yourself about how much runway (read, cash flow) you have and use it wisely to plan your next steps. A business can be reborn out of its ashes but only if it doesn’t screw employees, creditors and partners in the process. One friend who shuttered his business went on to immediately start another that he sold in just five years. By not burning bridges he made sure that his network of partners and suppliers was ready to sign on for a new ride.

5 – Are you afraid of the business failing or of yourself failing?

How much of your ego is wrapped up in the business? Is your fear that you will go down with the ship? You will not. The two are separate entities. I know that’s hard to accept when you’ve worked so hard to build it, and although you may be bruised you will survive, you will go on. The legality of closing down a business does not extend to your experience, knowledge, and competency.


Lastly, I’ll offer up one piece of advice that a very wise person once gave me; “It may get worse, but it will also get better.” When we are in a moment of crisis perspective is a hard, if at all possible, thing to achieve. Surround yourself with people who still believe in you, even if you have temporarily lost the ability to believe in yourself. You are an entrepreneur, you’re a fighter, you will come back, you will find new opportunities; your ambition is not gone it’s just taken a detour.

Picking yourself back up is the stuff you’re made of, and the sooner you make the decision to dust off the past the sooner you can build the future.

Tom Koulopoulos is the author of ten books and founder of the Delphi Group, a 25-year-old Boston-based think tank and a past Inc 500 company, which focuses on innovation and the future of business. He is also an adjunct professor at the Boston University Graduate School of Management, an Executive in Residence at Bentley University, the past Executive Director of the Babson College Center for Business Innovation, and a frequent keynote speaker. The late Peter Drucker once said of his writing, that it challenges not only the way you run your business but the way you run yourself. Tom’s latest book is The Gen Z Effect: The Six Forces Shaping The Future of Business.

This post was originally published on Inc.com.

The opinions expressed herein or statements made in the above column are solely those of the author and do not necessarily reflect the views of WTN Media