Dandelions and orchids: Why some people thrive as entrepreneurs and others flame out

It’s time to acknowledge an unpopular truth: Your success depends as much on your own personality traits as any online business tactic we could share. And this is why Eric Barker’s experience is instructive.

The author of the popular blog Barking Up the Wrong Tree, Eric spends day after day highlighting the habits of top performers in their field. And now, he’s distilled his insights into a single eponymous book that explores hundreds of examples, case studies, and scientific papers to answer a complex question: What makes someone successful?

Naturally, we asked him to turn his talents to the online business world. What sets a great entrepreneur apart? Below, we chat with Eric to learn how you can utilize your own personality traits to set yourself up for success.

(All according to science, of course.)

A main theme in the book is that our “bad” or “weird” personality traits can lead to our success. Can you give us your favorite example of this?

Jure Robič. He was the five-time winner of the Race Across America, a grueling bike race from San Diego to Atlantic City. The race is intense and usually takes 9 to 12 days. Outside Magazine declared it the most punishing event out there.

Jure’s competitive advantage? He would literally lose his mind and completely break with reality, like seeing secret meaning in the cracks in the pavement. He would jump off the bike and nearly attack his follow team. At one point, he thought he saw Mujahideen shooting guns at him. It enabled him to power through the most grueling parts of the race and avoid sleeping as much.

Now, I’m not suggesting you do the same. The important thing here is context. Given the right context, these “negatives” can be positives.

For example, we say some people are “stubborn.” But if you’re doing something hard, that’s not stubbornness, that’s grit. That’s determination. When you are talking about the heights of success, staying at the middle of the bell curve doesn’t help you.

How can an entrepreneur find the right context for them?

You need to start searching. It sounds obvious, but it’s true. Jure wouldn’t have thrived working in an office or starting a business. If where you are isn’t working, you need to identify your signature strengths. Both work and happiness research back this up. You need to figure out what you’re uniquely good at. The more time you spend on that, happiness markers go up, but most people don’t even take inventory of what they are good at.

This is essential for people trying to be an entrepreneur, where there is way less structure. Ask yourself, “How do I create an environment that leverages my strengths?” It’s far more easy to double down on what you’re good at than try to improve your weaknesses.

For example, if you’re extremely creative but not organized, focus on your creativity and get an assistant who keeps you organized. That’s better than suddenly trying to become organized.


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Eric Barker
Eric Barker

What’s one of the biggest misconceptions we have about success?

A lot of people confuse “success” with safety. When you’re a kid, your parents say they want you to be successful. And they do! But what they really mean is that they want you to be safe. There’s a difference in playing to win versus playing to not lose.

Living and not-dying are two different perspectives. That’s a distinction that sounds subtle but makes all the difference.

Do you generally believe most people are a little too safe?

I’m reminded of the metaphor of the dandelions and orchids. It goes like this: Some people are dandelions. You don’t plant them. They pop up wherever and they are incredibly resilient. And they breed like wild so you don’t need to do anything to help them grow.

But orchids? Those are very difficult to raise. They need a special temperature and special feed or they will die. But if they are handled well, they are the most beautiful flowers out there. Some people are sensitive to their contexts like orchids. Some aren’t. It sounds flowery and silly, but it’s the common metaphor used in the most cutting-edge genetics research.

You see this theme come up again and again in topics like leadership. Some people are comfortable with hierarchy and rising to the top, but don’t produce sweeping changes. They’re dandelions.

Then you have other people who don’t play by the rules, leaders who come into situations when they are difficult and produce huge changes. Sometimes those changes are negative. But sometimes those changes are amazing. They exist at the ends of the bell curve. They’re orchids.

It’s about understanding where you are on that curve and understanding your level of risk tolerance and conformity and then calibrating. It’s about knowing yourself.

This kind of self-assessment is difficult. How can we achieve this level of honesty with ourselves?

They say a tiger doesn’t change its stripes. Look back at your past. What environments did you thrive in? What events did you drive? What decisions did you make? We all tell ourselves stories, but if you’ve been on this planet long enough you can look at what you’ve done that made you really happy and start to get an understanding.

Then you can say, “Hey I’m trying to do my own thing but I actually want more rules, this is really hard for me. Maybe I should work for someone else.” Or “I’m trying to do my own thing at work and I’m feeling stifled. My strengths aren’t being utilized. I need to be an entrepreneur.”

Right, but big choices like this are rarely black and white. How do we do this?

Determine your personal definition of success. Is it to make a lot money? Is it to be happy wherever you are? Life is like buying a suit. Do you take it off the rack? Or do you get it tailored?

The only way to be successful and happy in the modern era is to have a personal definition of success versus doing what society tells you to do. We are in this unprecedented era of options. You have so many options and we’re being bombarded with examples of the richest, most successful, most skilled people from all around the planet. You can’t do that. It’s unrealistic. You have to know for yourself what your definition of success is, because it’s something you can achieve.

This is especially a factor in online business. We can read so many blog posts about someone’s big launch and then feel behind.

When I spoke to Swarthmore professor Barry Schwartz, he said this is something that’s going to drive us crazy. He’s shown that, when you know there are tons of options and you chose badly… who do you blame? Whose fault is it? It feels like it’s yours. This is a prescription for depression.

When things go wrong and you know you could have chosen better, you blame yourself. So, have a personal definition of success. Know what YOU need. Decide what “good enough” is. That’s anathema in American culture. But in a world of a billion options, you can’t go through them all.

But if we impose all this structure on our lives, won’t we get boring and predictable?

Absolutely. So you need to have structure for no structure. There’s a book by Peter Sims called Little Bets. He puts out the idea that 90% of the time, show grit and chip away at big important things. Be reliable. Double down on what’s important. And 10%, be a total flake. Try stuff that probably won’t work. But even if it doesn’t work it can open up new avenues for you.

Richard Wiseman did research on luck that showed this was a factor. Luck isn’t magic. Serendipity can be engineered. People who try new things, people who are more extroverted, people who are more optimistic are consistently luckier. If you lock the door and never leave the house how many lucky things are going to happen to you?

Ready to improve your habits and level up your life? Download our FREE Ultimate Guide To Habits below.