5 Signs You're Ready to Stop Planning and Start Doing
Stop waiting for the perfect plan. These 5 signs reveal you're already ready to start building your business—you just don't realize it yet.
Read ArticleStop Waiting to Feel Ready (You Never Will)
By Art Harrison • June 3, 2025
Stop waiting for the "right time" to take risks—it never comes. Learn why successful entrepreneurs act despite fear and uncertainty, and discover the real cost of endless deliberation. From a $60 million business story to practical advice on overcoming analysis paralysis, this is your wake-up call to stop rehearsing excuses and start taking action.
I've been thinking a lot about waiting lately.
How much time I've wasted sitting on decisions, convincing myself that I needed just a little more time, a little more certainty. Like there was some magical moment coming where everything would fall into place, and I'd finally feel ready to take the leap.
Spoiler: it never came.
It's funny how convincing those arguments are when you're inside them. "Let me save up a little more." "I'll wait until the kids are older." "I'll just finish this project first, and then I'll have time." And you believe it, because it sounds so reasonable. So logical. But if I'm honest, it was never about needing more time. It was fear, every single time.
The Decision That Changed Everything
I remember this one decision—I was debating whether to leave a stable job for something risky, something I wasn't even sure I could pull off. It was all-consuming. I made pro/con lists. I had endless conversations with friends, with my wife. I Googled, researched, stared at the ceiling in the middle of the night running through worst-case scenarios. Weeks of this. Maybe months.
And then one night, my wife just looked at me and said, "What are you so scared of?"
And I didn't have an answer.
I mean, I could've said failure. Or regret. Or humiliation. Or some long-winded excuse about how the timing wasn't right. But none of it felt real in that moment. Because what I was actually scared of was the part nobody talks about: what if I succeed?
Seriously. What if I actually pulled it off? What if it worked? That's terrifying in its own way, isn't it? Succeeding means change. It means new problems, new responsibilities, new expectations. And I think, deep down, I wasn't sure if I was ready for that.
The irony is, I did it anyway. Wrote the resignation letter, walked into my boss's office, and quit. Not because I had a sudden burst of courage, but because I realized I wasn't going to feel ready no matter how long I waited. So why not now?
This kind of endless deliberation is what many call analysis paralysis—where we research and plan indefinitely to avoid the discomfort of actually starting.
The Ungraceful Reality of Starting
It wasn't a graceful leap, by the way. I was a mess—sweating, second-guessing, fighting the urge to backtrack. I wish I could say it felt like freedom, but it didn't. Not at first. It felt like chaos.
And yet, looking back, it was one of the best decisions I ever made. Not because it worked out. It didn't, not exactly. But because I finally got out of my own way. I stopped waiting for life to hand me permission, and I just started.
That's the part nobody tells you. Starting isn't some epic, Hollywood moment where the music swells and the hero takes a dramatic first step. It's awkward. It's clunky. It's half-baked ideas and stumbling and sheer panic. But it's also the only way to get anywhere.
The $60 Million Lesson
Let me tell you about another time I had to make this choice. About seven years ago, a friend came to me with a business idea. He wanted me to join him, but I wasn't sure if I was willing to take that type of risk. I had so much in my life that felt like I should focus on it instead of starting something new.
I remember sitting on the back porch with my wife, and I remember her both insulting and encouraging me at the same time. She said, "Art, this idea is so much bigger and better than any idea you've ever had." (That part hurt—nobody wants to hear that their friend's ideas are better than theirs.)
"But you have to do it," she continued. "You have to take this opportunity because not only will you regret it if you don't, but you will learn so much. This will be like getting your MBA because the scope of it is just so much bigger than anything you have access to right now."
She knew me better than I knew myself. She knew that I would regret it. She knew that my ambitions were to be out on my own, to do something that had the potential to be huge. And she knew all the reasons why we shouldn't do it.
We had a four-year-old and a six-year-old. We knew how much we owed on our mortgage. I was making $150,000 a year. But she still knew it was the right thing to do.
So I wrote another resignation letter, and I am so grateful that I did.
At one point, that business was valued at over $60 million. We had 100 people working for us. I could have never even imagined that on that evening. But I also couldn't have imagined that in the course of about a year or two, we went from $60 million to selling that business for a little over $10 million.
That's a huge change. It was a huge disappointment at the time, but I still don't look back with any regret whatsoever because it was still life-changing. It's what gave me the freedom and the confidence and the experience I'm using right now.
The Myth of Perfect Timing
Here's the thing: I've never met anyone who felt ready. Not really. Every person I've ever known who did something bold or scary or transformative has said the same thing. "I wasn't ready, but I did it anyway."
And you know what? They were fine. Actually, they were more than fine. They were better for it. Not because everything worked out perfectly—because it rarely does—but because they started.
There is never going to be the perfect or the right time to do it. That I can tell you for sure.
When I was starting that business, I knew all the reasons I shouldn't do it. I knew that my kids needed both of us at home. I knew that our expenses were only growing. There were going to be repairs on the house, college funds to worry about, aging parents to care for. There was all kinds of reasons not to do it.
But if I had waited, things would have only gotten more difficult.
Here's another piece of advice: life doesn't magically get easier at any point. Your expenses and responsibilities will continue to increase as you get older. You might have nicer things, but your outflow will increase as well.
So waiting for some magic number in your bank account, a new title, or the "right" moment? It's just not going to happen.
The Real Question You Should Ask
I think about all the people I know who are waiting. Waiting for the right time to ask for a raise. Waiting to start the business they've been dreaming about. Waiting for the perfect idea, the perfect opportunity, the perfect excuse to finally take themselves seriously.
They tell themselves it's not the right time yet. That they'll know when it is. But will they? Or will they still be sitting there five years from now, telling themselves the same story?
The right time to do anything was yesterday. The second best time to do it is right now.
Whenever I'm facing one of these decisions, whenever there's a risk I want to take, I ask myself: What's the worst that could happen? Is the upside greater than the downside?
Most of the time, we fear things that aren't real. We exaggerate what the negative outcome is going to be. We assume that if we start a business and it doesn't work out, our life will be ruined.
But that's not the case. If you start a business and it doesn't work out the way you expected, that's okay. You're going to learn so much. You're going to make new connections. You're going to have the muscle memory of starting something, knowing that it's easier than you ever imagined—and that's going to open you up to do it again.
The Art of Just Doing
One of the things I can tell you as a fact—something I've heard over and over again from other founders, entrepreneurs, investors, and executives—is that there's no difference between them and the people that work for them other than their willingness to try.
They're not any smarter. They're not necessarily better educated. They don't have more access. They're not predisposed to being that way. They just found it within themselves to give it a shot when there was an opportunity or an idea that they just couldn't shake.
That's all it takes.
Think about it in the simplest way. You want to learn how to play guitar. You could think about it every single day. You could study the best videos and courses. But if you weren't picking up the guitar and playing every single day, just experimenting, would you be better in a year than someone who picked it up for an hour every day and just tried?
Of course not.
The art of just doing is so much more valuable than sitting and thinking or worrying about all the potential downsides. This is a key aspect of building real entrepreneurial confidence—learning to act despite uncertainty and discomfort.
What Are You Really Waiting For?
I don't know who needs to hear this, but maybe it's time to stop waiting. To stop rehearsing the story of why you can't or shouldn't or don't have time. To just write the resignation letter, or buy the guitar, or start the thing you've been dreaming about for years.
What's the worst that could happen?
You fail? You pivot? You make a fool of yourself and learn something in the process? Sounds like a pretty good deal to me.
If you want to change your life, at some point you're going to have to pursue an opportunity that makes you uncomfortable. You're going to have to say yes to something. You're going to have to be one of those people that takes risks.
Sometimes they're going to fail horribly. Sometimes it's not going to turn out at all like you imagine. And other times, it will be somewhere in the middle. But it's still something worth doing.
The only real question is: What are you waiting for?
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Video Transcript
This idea is so much bigger and better than any idea you've ever had. What if this time you just had f*** it? I'm gonna try. But if you cast aside all the fear and the doubt that you have, all the voices that we all have, whenever we're faced with one of those decisions, and just decided that you were gonna go for it. How much could that change your life? How much could that open you up to new opportunities and experiences if you were just willing to actually give it a shot? That's what we're gonna talk about today. We're gonna talk about a lot of the risks that I've taken because I have taken a lot in my life. We're gonna talk about whether or not it's worth it. How people delay things because they're waiting for the right time or because they have a backup plan that's actually stopping them from getting started to begin with. You can just tell much more you learn from actually doing things than just thinking about them or worrying about what the outcome would be. Now, if your new here, my name is Art. I'm a former founder, I'm a lifelong entrepreneur, and as I said, I've taken a lot of risks. And every single time I took one of those risks in my life, I felt the same way you probably feel right now. I felt anxious, I felt that fear in the pit of my stomach, but there was always something inside of me that made me push through. It was either an internal voice or sometimes an external voice, and I still remember everyone of those decisions vividly and I don't regret a single one of them. I can tell you that I remember writing every single resignation letter. I remember where I was, how I felt and I remember the anxiety I had handed it in. I feel the same way, but every time I had to tell my parents or my friends that I was giving up something that I had worked towards, or that they thought was important to pursue something that I wanted, and that I felt was the right choice for me. The one that stands out the most to me, and I think it's relevant to most people out there, was the reason that I'm actually here making this video for you right now. About seven years ago, I had a friend come to me and he had the idea for a business. He wanted me to join him, but I wasn't sure if I was willing to take that type of a risk. It's so much in my life that felt like I should focus on it instead of starting something new and making a new sacrifice. So I went home, I remember sitting out on the back porch with my wife, Lindy, and I remember her both insulting and encouraging me at the same time. I still remember the word she said. She said, "Art, this idea is so much bigger and better than any idea you've ever had." That's the part that hurt because nobody wants to hear that their friends' ideas are better than theirs. But the part that encouraged me was when she said, "But you have to do it. You have to take this opportunity because not only will you regret it, if you don't, and you see someone else succeeding. But you will learn so much. This will be like getting your MBA because the opportunity, scope of it, is just so much bigger and more impressive than anything you have access to right now." She knew me better than I knew myself. She knew that I would regret it. She knew that my ambitions were to be out on my own, to do something that had the potential to be huge, and she knew all the reasons why we shouldn't do it. She knew we had a four year old and a six year old. She knew how much we owed on our mortgage. She knew that I was making $150,000 a year, but she still knew that it was the right thing to do. So I went in that night, I wrote another one of those resignation letters, and I am so grateful that I did. She said at the time that she didn't know whether it was going to succeed or not or how big it would get, and she was right about that as well. At one point that business was valued at over $60 million. We had 100 people working for us. I could have never even imagined that on that evening. But I also couldn't have imagined that in the course of about a year or two that went from $60 million to selling that business for a little over $10 million. That's a huge change. It was a huge disappointment at the time, but I still don't look back with any regret whatsoever because it was still life changing. It's what gave me the freedom and the confidence and the experience we're doing this right now. And that's why I really wanted to talk to people about making those choices about making the decision to just say yes and to try things in your life. One of the things I can tell you as a fact that I have heard over and over again from other founders and entrepreneurs, from investors, from executives, is that there's no difference between them and the people that work for them. The people they meet other than their willingness to try. They're not any smarter. They're not necessarily better educated. They don't have more access. They're not predisposed to being that way. They just found it within themselves to give it a shot when there was an opportunity or an idea that they just couldn't shake. That's all it takes. If you want to change your life, at some point you're going to have to pursue an opportunity that makes you uncomfortable. You're going to have to say yes to something. You're going to have to be one of those people that takes risks. And sometimes they're going to fail horribly. Sometimes it is not going to turn out at all like you would imagine. And other times, it will be somewhere in the middle like my last one was. But it's still something that is worth doing. And there is never ever going to be the perfect or the right time to do it. That I can tell you for sure. I knew when I was starting that business, all of the reasons I shouldn't do it. I knew that my kids needed both of us at home. My wife needed us at home. I knew that our expenses were only growing. Not only did we have young kids, but we needed to be saving for college. There was going to be repairs on the house. There was all kinds of reasons not to do it. But if I had waited, things would have only got more difficult. That's another piece of advice that I want everyone in their 20s and 30s to understand is that life doesn't magically get easier at any point. Maybe if you become a billionaire and you have absolutely no expenses and unlimited funds available to you. Maybe life is easy then. But I can tell you as someone that has made a hundred thousand to two hundred thousand or more in a year, your life doesn't instantly get easier. Some of it does. That's fair. Believe me. It is a lot easier when you're making that kind of money. But you end up with other properties, with car payments, you end up with college funds, you end up with repairs, you end up needing to care for your parents who are aging. There's always going to be a reason that prevents you from making the changes you want to make. And you're not going to feel immensely more wealthy as you get older. You might have nicer things, but your expenses, your outflow will continue to increase as well. So waiting for some magic number, something in your bank account, a new title, just a dollar figure that you feel is going to then put you in the right place to propose to your partner to start a business, to try your hand at something on the evenings or weekends as a side hustle. It's just not going to happen. There's no such thing as a right time and you just need to accept that the right time to do anything was yesterday. The second best time to do it is right now. So if there's something you're thinking about, you just have to ask yourself, what's the worst that could happen? Is this worth it? Is the upside greater than the downside? That's honestly the question I ask myself whenever I'm facing one of these decisions. Whenever there's a risk I want to take, I want to know what is the real worst that could happen if I do it and it doesn't succeed. If the worst is catastrophic, if there's a potential that I'm going to lose my house, if my wife might leave me, my kids might be destroyed or emotionally impacted, then yeah, maybe I won't do it. But most of the time, that's not the case. Most of the time, we fear things that aren't real. We exaggerate what the outcome is going to be in a negative way. We assume that if we ask the person out and they say no, that our life is going to be ruined. I'm sure most of you have asked someone out and been rejected before or rejected someone and watched yourself or them go on to still live an amazing life. If you start a business and it doesn't work out the way you expected, that's okay. You're going to learn so much. You're going to make new connections and people. You're going to have the muscle memory of starting something. I'm knowing that it's a lot easier than you ever imagined and that's going to open you up to do it again. There's very few people that succeed on the first try. So just doing it is the best possible thing for everyone because you learn so much. And that's really the last point that I want to make is that learning is one of the most valuable things that you will have from your career throughout your career. The more you learn, the more experiences you have, the easier it becomes to make future decisions. The more knowledge you have, the more valuable you become as an employee, as a founder, as anything else because you have tried. I talked about this in my video about failure, but there's a wonderful story about someone teaching their class to make the perfect pot. I told the whole story back then, but basically it's just that half the class made a pot every single day and the other half tried to make the perfect one. And at the end of a month, all of the best pots came from the group that just kept experimenting and trying. Not the ones who tried for perfection and that's true for everything you do in life. And the more you try and experiment and grow, the more that knowledge becomes an exponential advantage over everyone else. Just think about it in the simplest way. You want to learn how to play guitar. You could think about it every single day. You could study the best videos and courses, but if you weren't picking up the guitar and playing every single day, just fiddling around trying out new songs, experimenting with new genres. Do you think you'd be better in a year from now than someone who every single day for an hour just picked it up and tried? Of course not. You might have heard some great things, but when it came time to put your hands on the strings, to figure out how to actually do it to understand what it takes to build the calluses that you need to perform, you wouldn't have even begun. Now imagine doing that for five years or ten years. The art of just doing is so much more valuable than just sitting and thinking or worrying about all of the potential downsides. Take it from me. Take it from someone who has lived a life full of failures and successes, who will raise their hand at any opportunity to stand on stage. Sometimes in a fantastic way where I hear applause and laughter and other times where I hear dead silence, what I've done and what I'm encouraging all of you to do is to simply try because you will get better. And new opportunities will come from those experiences, even the negative ones that will ultimately lead you where you need to go. And if you need another little push to get over the edge, to take that chance, I recommend you watch this video because a lot of people use the wrong fear to drive their lives for it. Don't use failure. Use regret as the thing that motivates you to make the change. Check out this video. I really think it'll help you.