Keep failing. You got this.

Jason Bennett
5 min readSep 27, 2022

Why failure is so important as an entrepreneur and the takeaways that lead to success

Like many of you, in my journey as an entrepreneur, I've had my share of mistakes, and failures. With my first start up I was destined to fail! Here’s what I did wrong; 1) I was in it for the money. Chasing the dollar, not having the passion needed to fight through. 2) I thought I knew everything. (Biz ops, done it. Rev ops, done it. Solving a big problem, done it. Leading/scaling go to market of a vision/concept, done it. Building teams, done it.) 3) I didn’t accept the signs that we were too early in the market. 4) I was arrogant! Arrogant until the end believing we’d be ka-gillionares. I wasted time building features without validating demand. I had my head in the sand, building instead of selling. I’m a metrics guy! I ignored my own metrics showing that we should pivot.

What did I learn from this experience? A great deal; a hell of a lot! I learned that failure is part of the process and more importantly, it’s what you do with that experience that makes the difference.

Here are first-hand lessons learned that will without doubt help you on your journey.

Stopping the rumination cycle is key

Live in the present

The past is the past, live in the moment and move on. This is such an easy thing to say and extremely difficult to achieve. How can we live in the present when we are constantly planning for the future or worrying about the past? Living in the moment means no longer worrying about what happened in the past or fearing what will happen in the future. According to Tchiki Davis, MA, PhD, of the Berkeley Well Being Institute, stopping the “rumination cycle” is key. Ruminating is the act of staying focused on the problem, the feeling, the experience and not taking any action to resolve them. He says “When we live in the present, we may still have negative emotions about things that happen to us. But instead of turning them over and over again in our minds, we take actions to change those emotions in the moment.” Focusing on the past blinds you to the present.

Your mistakes, not your perfect record, make you more desirable as an entrepreneur

You are stronger than you think!

What do I mean by this? Keep putting one foot in front of the other. You have the ability to keep going even when fear and doubt are telling you that you can’t. I certainly need this reminder a lot and you might too. What makes some people, and not others, get up time after time after a defeat while others crumble?

I think it’s the ability to keep things in perspective. Knowing when to pat yourself on the back and when to self-assess. In this CNET article by Zachi Zach, Zachi points out that “failure is one of the entrepreneur’s most valuable assets.” Most of us can see our shortcomings way easier than we can see our successes and we beat ourselves up after every setback. Don’t dwell on the failures, it does you no good. Give yourself a break and keep at moving forward.

“Acceptance means no complaining. And happiness means no complaining about the things over which you can do nothing”. — Dr. Wayne Dyer

Complaining is not [really] a solution

To put it simply, complaining stops with finding the problem, problem solving involves taking action to find a solution. As humans, we all complain. It’s a way of managing our emotions, venting may feel like a way to lessen the severity of negative feelings. In 5 Reasons Why People Complain, an article by Habits for Wellbeing, they say the reasons we complain are to get attention; remove responsibility; inspire envy; power (the wrong kind); and to excuse poor performance. Any of those striking a chord?

So, how can we get out of this mindset? We can start by airing valid concerns. Step back and look at the big picture, will any of this even matter in a week, next month or next year? Find the positives, if all you do is complain, people will shut down and completely miss your message. Lastly, gratitude is Key! Reminding yourself every day about at least one thing you are grateful for can help break the negative, complaining habit. Let go of the little things and focus on the solution.

It’s not all about you!

We all do it. We don’t get the deal we wanted or the acknowledgment we think we deserve. After all, we have the title and the knowledge, why would someone turn us down or not follow and respect us? Our human nature is to be self-absorbed. As a result, we communicate from our own perspective instead of the other people. Statistically, it takes approximately 23 no’s to get a yes. What I have learned over the years is that it’s not personal. It’s just business. Don’t take it personally! Leave your ego at the door. If someone turns you down, they aren’t the right client for you. Knowing it’s now all about you is also realizing that your business is about your clients more than it is about yourself. If you fail to provide a service that someone else is willing to pay for you are out of business. It’s as simple as that.

You don’t always get what you want. Sometimes you have to make sacrifices.

To quote The Rolling Stones, “You can’t always get what you want, but if you try sometimes, you just might find, you get what you need”.

The truth is in negotiations (both in business and life) the likelihood that you will get everything you want is slim. Too many people have deals go up in smoke by losing sight of the fact that it’s about getting what you need. In a great negotiation, everyone comes out a winner. Something that I have learned the importance of is knowing your “walk away” point. If you know what is absolutely non-negotiable for you and your business, you can save yourself the time and agony of lengthy negotiations and jobs that are not suited to your business.

I’m Jason Bennett, a serial entrepreneur and life enthusiast who writes about Enterprise SaaS trends, the founder's journey, and self-improvement.

Follow me on Twitter or LinkedIn. Check out my website

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Jason Bennett

I’m an entrepreneur, advisor, and VR fitness nut who writes about SaaS growth tactics, the founder’s journey, and lifehacking.