Note: you can listen to this episode above or load it up in iTunes.

How to Develop the 7 Habits of Lucky Entrepreneurs

Today’s episode is all about how to increase the chances of lucky things happening to you. Some people believe luck is random or based on personality, but I believe luck is a choice. You can choose to increase the chances of lucky things happening to you by creating conscious habits. Today I share the habits you can choose to develop to grow your own luck as a blogger and entrepreneur.

Close-up shot of four-leaf clovers in a field. by Vitalina Rybakova on


In This Episode

You can listen to today’s episode above or in iTunes or Stitcher (where we’d also LOVE to get your reviews on those platforms if you have a moment). In today’s episode:

  • How one email changed the trajectory of my life
  • How to be in the right place at the right time
  • How to gather information and knowledge to increase your luck
  • How lucky entrepreneurs respond to problems
  • How lucky entrepreneurs practice curiosity
  • How to set aside time to watch for sparks that you can fan into big flames of success
  • How to create and develop things instead of spending all your time reacting
  • How to make small changes today that will take you to a different place in the long run, helping you to evolve

Further Reading and Resources for the Habits of Lucky Entrepreneurs

The 2 Questions to Ask Yourself Every Day:

  1. What gave me energy today?
  2. What did I do today that seemed to give other people energy?

My ideal weekly schedule that I created to remind myself to regularly focus on cultivating the habits of lucky entrepreneurs (note: this is an updated version from one I shared a few episodes ago):

Screen Shot 2015-09-17 at 8.52.45 pm

Full Transcript Expand to view full transcript Compress to smaller transcript view
Hi there. My name is Darren Rowse and welcome to the ProBlogger Podcast episode 45 where today, I’m going to talk a little bit about how to get lucky. No, not quite luck. You might be thinking I want to talk about getting lucky in business as an online entrepreneur or as a blogger. I’m going to tell a little bit of my story of luck in my journey but give you also seven tips to increase the chances of lucky things happening in your own journey as a blogger. You can find today’s show notes at

Have you ever been in the right place at the right time? I certainly have been, numerous times along that way in my own blogging, right back at the first moment when I first discovered the first blog. I did have a little bit of luck. I was in the right place at the right time. It was a rainy afternoon in November 2002. A Friday afternoon, if I remember correctly, and I was sitting at my computer at one of the part-time jobs that I was doing at the time. A voice came out of my computer. It was a bit of an embarrassing voice, now that I think about it. It said, “Master, you’ve got mail.” I was a lot younger back then and a bit more immature. I’m not sure why I installed that little plugin. 

But I went and checked my Hotmail account and there was an email from a good friend of mine, Steve. It was the kind of email that I normally would’ve probably passed over and not paid a whole heap of attention to because it only had four words in it. It was one of those emails where someone sends you a link and you never quite know what you can end up on when you click those links. The email basically said these four words, “Check out this blog.” 

I never heard the word blog before. It was 2002 and I wasn’t familiar with that term, so it made me a little bit curious. I clicked the link and I ended up on this blog called Now, the blog itself, I was interested in.

To cut the long story short, it was this medium of blogging that really grabbed my attention on that day. To cut that long story short, 3½-year long story short, I started a blog that day. In doing so, it really did change the trajectory of my life. That sounds quite dramatic, but it really did change my life. Today, 3½ years later, I’m a full-time blogger, I have over 5 million people a month to check out my blogs. I’m also not the biggest or the best blogger out there. I sometimes wonder, what would have happened if I hadn’t clicked that link? It was one of those sliding door moments in my life. I was in the right place at the right time. 

I’m often asked, how much of your success was to do with the fact that you started in 2002? I guess I reflect that. It was a great time to get that email. 2002 was a brilliant time to start blogging. Even though at that time I felt like I was too late, I looked around and saw the other bloggers that were more established. In hindsight, it was very early days. There was this rise in the interest of new media. Social media hadn’t even really been born as a term (although, this blogging was really the beginning of it) and I’ve been writing that wave of interest in blogging and social media ever since.

In some ways, I was lucky. It was serendipitous that I got that email at that time and I paid attention to it and acted upon it. I was lucky. As I looked back over the last 13 years, there’ve been many moments, lucky moments along the way. Being in the right place at the right time, meeting the right person at the right time, chance encounters, things coming out of the blue have helped me to grow my blogs. While there’s also been a whole hip of hard work, strategy, there was also serendipity along the way.

If you’ve been following me for a while and have listened to podcasts, interviews that I’ve done, webinar interviews that I’ve done in the past, you will have heard me asked a question of many online entrepreneurs. I quite like to ask them about this idea of serendipity. The question I’m asking quite a few people, both in conversations but also on Webinars is, has your success had more to do with serendipity or strategy?

Now, strategy always plays a part. Hard work always plays a part in success, but so too (as I’ve found) does serendipity. It’s amazing how many online entrepreneurs tell me, “You know? There was this moment where I was very lucky.” It’s often at the beginning of the journey. What I find is often, serendipity opens the doors in many cases and then, the strategy often comes later.

It’s not always the case, but as I’ve read a lot about entrepreneurship, I do see this recurring theme. Luck seems to play a part, serendipity or happy accidents seems to be a part of entrepreneurial stories. As I look at these stories and as I talk to online entrepreneurs, I’ve also noticed that these lucky entrepreneurs also seem to share traits, also seem to share qualities, and sometimes I think of them as personality traits, but also, it seems to be more about the way they spend their time. They tend to do things that seem to open up the luck opportunities, increase the chances of lucky things happening to them.

Today, what I want to talk about are seven habits of lucky entrepreneurs. These are seven things I’ve noticed behind the lucky encounters that seem to play a part in increasing the chances of lucky things happening. By no means of this, the only seven things are not a definitive list and I would love to hear what you think of them, I’d love to hear what you would add to them as well. Let’s get into them.

The first one is that these lucky entrepreneurs seem to be, more often than not, avid learners. Not all of them have high educational qualifications. In fact, many of the online entrepreneurs that have the most success that I’ve come across don’t have any at all but they all seem to be avid learners. They are the type of people who read a lot, listen to a lot of podcasts, or go to a lot of conferences. They’re gathering information and knowledge. They’re also the type of person who asks a lot of questions.

I’ve got one quite successful entrepreneurial friend. We catch up for a coffee every now and again. He’s the type of person you sit down for a coffee and he just peppers you with question after question after question. I don’t even think he does it on purpose, he just can’t help but gather knowledge at every time he has an interaction with someone. It’s not just me, he does it with everyone he meets. He just can’t help but gather information whether they’re an expert or not. He understands that everyone knows something so he wants to pick their brains.

These online entrepreneurs, these lucky entrepreneurs also have mentors. More often than not, they’re a part of mastermind groups. They put themselves into situations where they will learn information. Now, what’s this got to do with luck? There’s a Roman philosopher by the name of Seneca. He once said—you might have heard this quite before—”Luck is what happens when preparation meets opportunity.”

What I think is happening here is that when you have the knowledge, when you are educated, when you have learned something, you’re more likely to be able to make lucky, educated guesses. When you have the knowledge, you’re also luckier to be able to notice and see how to leverage and take advantage of anomalies and opportunities that come your way. When you have the knowledge, you’re more likely to be able to join together dots that have previously been disconnected. Knowledge helps to prepare you for lucky instances to notice them but also, to make luck. 

The question I’d ask you today is are you filling your cup? This is something I’ve talked about in previous podcasts, but it’s worth talking about it again. Are you actually learning? Are you putting yourself to a position where you are learning? Do you read? Are you listening to podcasts? Well, you’re obviously listening to this. Are you going to conferences? Do you have a mentor? Are you part of mastermind groups? Are you asking questions of those you meet? Are you putting yourself in a position to learn?

What I would encourage you to do is to set aside time to learn. All of these habits that I’m talking about today, I think you can actually develop systems and you can put aside time to do these things. My argument today is that these seven things are choices. These are not personality traits, these are choices. The way you spend your time can help you to have these lucky instances happen. Of course, there are many other benefits of setting aside time to learn as well. So, set aside time to learn.

The second habit of lucky entrepreneurs that I want to talk about today is that they seem to be fascinated with problems. The lucky entrepreneurs that I’m thinking about have this really positive way of viewing problems while most of us are wired almost from birth to avoid problems at all cost, to run away from them, to complain about them, to avoid them, to take shortcuts to get around them. Lucky entrepreneurs actually embrace problems. They’re very optimistic in the way that they view problems. 

Problems are not something to be avoided, they’re not something that should be seen as a roadblock. They’re actually springboards into opportunity. They’re signals of solutions, said one person that I met recently. He talked about how, when he comes across a problem in his own life or in someone else’s life that he actually sees them as a signal to a solution. He admitted to me that he hears a little “cha-ching,” sort of like a cash register sounds when he comes across a problem. That’s the way he trained himself to be. Again, this is a choice. How we react to problems is a choice. 

The question I’d ask you today is how do you respond to problems, both your own problems and the problems of others? Do you even notice them at all, other people’s problems? Another question related to this is do you capture those problems? Do you have a system to notice, but also take special notice of problems? Because problems could be opportunities. Particularly as a blogger, noticing the problems of your readers is a very powerful thing and having some system to collect those problems is really important. I’ve talked in previous podcasts how I used Evernote to make note of these types of things, the question that I hear but also the problems that I noticed in my readers.

The third habit that I want to talk about today is really building about this idea of embracing problems. It’s the way that lucky entrepreneurs respond to problems. They do so by practicing the art of curiosity. This is the third habit I want to talk about, practicing curiosity. Rather than running away from a problem, rather than complaining about a problem, the lucky entrepreneur responds to problems with curiosity. They play with problems.

It’s almost like this picture of a cat playing with a ball of wool. You know how they play with it, they tap it around, and they just, gently overtime, unravel the ball of wool. This is how lucky entrepreneurs respond to problems. They play with the problems, they enter into this playful state of asking questions about the problem. Many times, the questions start with the words what if. What if we try this? What if we try that? What would happen if we did this?

This is really hypothesizing. This is coming out with a solution, a playful solution to the problems. It’s often when we tease problems, it’s often when we play with them in this brainstorming away, this non-pressured, “we don’t have to find the solution, we’re just playing with the problem.” It’s often when we enter into this state that we see the light bulb moment happen. Curiosity isn’t a personality trait, it’s a choice. It’s something that we can choose to be and it’s something, I think, that we can try in ourselves to have. 

Next time you come across a problem, whether it’d be your own or a problem that you notice of someone else, I would encourage you not to run away from it but to embrace it and to embrace it with some of these what-if questions. Some of us are perhaps more wide to these things, perhaps personality does play a part here. But I believe you can set aside time to do this and it may be helpful to this with other people as well if you find this hard.

Set aside some time and tackle a problem. Brainstorm it, play with it, exercise curiosity in response to it. I actually have time set aside every week where I, by myself, just pull apart a problem and just brainstorm it. I also had people to do this with as well. That’s the third habit.

The fourth habit builds upon this curiosity. It is to experiment prolifically. Up until this point of noticing a problem, embracing that problem, and then practicing it out of curiosity, everything is still stuck in your head. You might have had a light bulb moment, but if this is where it stops, then it’s kind of useless in some ways. You’ve got to get that idea out of your head. The way that I see a lot of lucky entrepreneurs doing that is to experiment prolifically. 

I think someone like Leo Babauta from Zen Habits. Leo is the kind of guy who’s constantly experimenting. He’s constantly trying new things whether it’d be his diet, his exercise, or something else. Tim Ferriss is another person who does this. They’re constantly experimenting in their own lives. As a blogger, we have all kinds of tools at our fingertips that can help us to experiment. Particularly, I think about social media.

As I look back over my last 13 years of blogging, almost every product that I’ve created, every ebook (and we’ve released over 30 of them), every course (we’ve released a couple of them), the book that I’ve written, the event that I ran, almost every single one of these products started with a tweet, with a Facebook update, or with a blog post update, and these are seen as experiments. When I get an idea, my first reaction is to test it, to put it out there and to see whether other people respond to it, to see how things are responded to. Have I resonated with the sparks fly when I put the idea out there? 

The question I have here around this habit is do you have your ideas stuck in your head? I come across a lot of want to be entrepreneurs, people who really do want to be entrepreneurs, people who want to have online businesses whose ideas are stuck in their heads. I think the best thing that you can do is start to experiment.

You don’t need to create the perfect business on day one if you’ve got an idea in your head. You need to find a way to test it and it may be just a short tweet that tests that, blog post, maybe a conversation with someone, it may be that you build a prototype, or you build something that takes you towards that journey. You don’t need to create it on day one. Set aside time to test your ideas.

The fifth habit that I want to talk about again builds upon this. The fifth habit is to create time, to set aside time to watch for sparks. This is really the next step after the experiment. An experiment is great, but unless you create time to watch to see how that experiment went, then it’s kind of useless even doing the experiment.

This is something that I think it’s really a big challenge for people today. The problem that we face today is that we fill every second of our life, every minute of our life with activity, at least many people do. They just don’t have time to observe and watch for sparks of opportunity.

Quite often when I go to a conference—I just got back from the Inbound Conference—it was interesting to see that there was this recurring question that I was asked at that conference. I reckon about 10 times in 3 days I was asked, “What’s your next big thing? What’s the next big thing for you, Darren?” It’s a great question, I love getting that question, I’ve asked it myself but the realization that I’ve had over the years is that my big thing, the biggest things that I’ve done have always started out as really tiny, small things.

The biggest products that I’ve created usually start as an idea that I get lying in bed at 1:00 in the morning, that I then test and I put it out there as a tweet or a blog post to watch to see what happens. It usually comes back as a small positive reaction from my readers. These little sparks of resonance, these little sparks of energy that I get in myself but I also see in other people, it’s paying attention to those little things that actually you can fan those little sparks into flames. 

Your next big thing might actually be the tiny little thing waiting to be noticed right in front of you right now. The question I have for you is do you have time to notice the sparks? Do you have practices to help you unearth those sparks of opportunity?

One of the things that I do everyday is at the end of the day, I ask myself two simple questions. I quite often ask myself these questions either before I go to bed or even in bed. I encourage you to do it before you go to bed because sometimes when you ask these questions, you have to get up and write down the answers. These are the two questions I ask myself every night.

It’s kind of a meditative exercise, although not a spiritual one, it’s just a mindfulness exercise in some ways. The two questions are these. One, what gave me energy today? What did I do today that gave me energy? This is about paying attention to the ideas that you’ve got, the things that you feel excited about or at least feel warm towards. By paying attention to the things that give us energy, we might just unearth something that is becoming a passion for us, becoming something that excites us. It’s often these things that can become our next big things. 

The second question is related to the first and it is, “What did I do today that seemed to give other people energy?” This is where you pay attention to some of those experiments that you do. What did you create today that other people responded to in a positive way? This might be a blog post that you write. Did you write a blog post story? Did you create a tweet that got lots of energy? Did you have a conversation today where when you talked, someone else got really excited about something that you said? By paying attention to what gives other people energy that you do, you see opportunities, all kinds of opportunities.

This is really something I learned to really pay attention to over the years, whether you do that kind of exercise, whether you get some other journaling exercise, or whether it’s just paying attention during the day to the opportunities that come. This is really important. My suspicion is that a lot of people aren’t lucky because they have no time to observe the opportunities that come their way. I suspect that lucky things happen to us all the time but many of us just don’t have the time to observe those lucky things.

Let’s get moving. The sixth habit of lucky entrepreneurs. I’ve noticed that lucky entrepreneurs are people who spend a lot of time creating, initiating, and constructing. Again, this is something I’ve talked about in previous podcasts but I suspect that most people don’t spend much time doing this.

Most people, in my observations, spend a lot of their time reacting to the agendas, the demands, the expectations of other people. Their time is spent in a reactive state. This is why most people work for other people, this is why most people spend a lot of their time in their email responding to emails. We respond to the demands, the expectations, the agendas, the questions of other people and there’s nothing wrong with that. Even as an entrepreneur, we need to learn to do that.

But the best entrepreneurs that I’ve ever come across are people who spend significant time creating. They spend significant time initiating, they spend significant time constructing. They don’t spend the majority of their time responding to what other people want them to do. They spend time forging forward on what they feel they need to do. Lucky entrepreneurs spend most of their time in constructive mode. This is what sets them apart, the most successful entrepreneurs, from the rest of us.

Here’s my big question for you on this front is are you spending most of your time being responsive or constructive? I’ll probably add another category. Are you spending a lot of your time being passive? Most people I come across are doing one of these three things. They’re being responsive and just responding to the agendas of other people or they’re being passive doing very little at all. Perhaps you might call them lazy, or are you being constructive? Are you being creative with your time?

As I said a few podcasts ago, this is something that I was challenged on earlier this year. I realized I was spending a lot of my time being responsive, I spent a lot of my time on social media responding to people and the agendas I had, I spent a lot of my in emails responding to the agendas of other people, and I needed to rebalance the way I spent my time. I set aside time in my week to create. 

The seventh habit of lucky entrepreneurs is that they have this ability to pivot. Success is rarely the result of traveling in a straight line. Almost every successful entrepreneur I ever met has told me stories of pivoting. Sometimes, pivots are massive pivots, 180 degree turns. But many times it’s just a small pivot, a change in direction, a subtle change in trajectory. This is the thing I’ve learned. Even small changes today, changes that you might not even notice looking from the outside can take you to a very different place in the long term. Just a small change in trajectory takes you into a different place in the long run.

The question that I have for you today is are you evolving? Is what you’re doing in building your business what you’ve always done? If you’re doing the same thing today that you were doing three or four years ago in exactly the same way that you were doing three or four years ago, it could actually be a sign that you are in a rut. It could be a sign that you have a problem because we’re kind of designed as beings to evolve and to change. Changes are a sign of health. If what you’re doing today is the same as what you’re doing a couple of years ago, you might want to ask yourself, should you have evolved? You should be changing at this point? Choose to change, choose to evolve, choose to pivot. 

I’ve just talked about seven habits of lucky entrepreneurs and as I said in the start, these are just seven ideas that I’ve had, seven observations that I’ve made, and I’d love to hear what you think. Here’s the thing about each of these seven things. They’re not personality traits. Some of us are maybe wired to do these things more easily than others but these are not personality traits, these are choices.

Lucky entrepreneurs choose to spend time learning. They choose to embrace problems and to respond to them with curiosity. They choose to spend their time experimenting, taking out ideas and their hypothesis, and testing them. They choose to spend time watching for sparks of opportunities. They choose to spend time building, constructing, creating. And they choose when the opportunity comes to pivot. As a result, I would put forward the argument that we can choose to do things that increase the chances of lucky things happening to us. 

I guess the question I’ll have for all of us today is are we spending our time choosing these things? It’s very easy to drift along in life. Just drift, to be reactive with their time, and to be passive with their time. The most successful entrepreneurs that I have come across actually unintentional about these things.

I talked about in the podcasts a few weeks ago on productivity about how I designed my ideal week. I’ve actually updated that design. In the show notes today, I’ll show you the update that I’ve come up with, the way that I spend my week. But simply by doing this exercise of creating the ideal week, you can plug in some of these sorts of activities and you’ll see in the one that I shared with you—I created a Google calendar of how I want to spend my ideal week—you can see that I’ve plugged in some of these different habits to help to stimulate these things. I’d love to see your examples of some of the calendars, the ideal weeks that you’ve created as well.

I’d love to hear your thoughts on this, what would you add to these seven habits. Do you think there are other things and there are a few others in mind that are almost put into this list but wanted to keep it a bit shorter? I’d love to hear what you think, the things that you think are missing, the things that you agree or disagree within this particular list. You can go to today’s show notes for this podcast at and leave a comment.

I’d also love to get your review of the ProBlogger podcast. Over the last few weeks, there have been some fantastic reviews. I came across one today from Ruth Turner from Dog Audity. She wrote quite a long review on iTunes, but in part, she wrote, “The 31 Days to Build a Better Blog series was the first podcast that I ever listened to. Not only did they get me hooked on podcasts but it was the best thing I ever did for my blog.” That’s fantastic to hear, Ruth. I really appreciate your leaving that review.

I love this one from Sam Nolan Smith as well. Sam writes, “Loving this podcast especially Darren’s down to earth and really practical approach to building your blog and your business. I still listen to someone who’s not hyping it, just sharing smart, actionable advice.” I love that particular review because I do see a lot of hype in blogging about the blogging space, in podcasting about blogging space. There are some great podcasts and blogs out there who don’t hype it up but sometimes it does get a bit hyped up. I do try and be as down to earth as I can, and is really sticking and helping people get realistic expectations. Thank you for your review as well, Sam. 

I’d love to see your review of the podcast. If you can pop by over at iTunes, leave a review. I’d love to hear your feedback. Again, you can find today’s show notes at I look forward to chatting with you in the next episode. Until then, I hope your blogging is going well and I’ll chat with you on social media. Bye for now.


How did you go with today’s episode?

What did you learn from today’s episode? Do you have any of these habits? What habit will you try to establish next? Has your success had more to do with strategy or serendipity? Have you created your ideal weekly schedule? We’d love to see it.

We’d love to hear from you in the comments below. Don’t forget to share a link to your blog.

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