Claiming Your Quirky Business Brilliance


I think we’ve all been there: We get an idea of a job we could get or a business we could start that would be amazing. We think, “if only I could do this for a living, or if only I could share this passion with other people who love it.”

But before long we quash our ideas. We tell ourselves it’s not realistic, we tell ourselves we’re not smart enough to make it happen, we tell ourselves that we’re just being too idealistic again. And we quit. We give up on our dreams, our ideas, and our hopes of finding or creating work that we love.

Why do we do this?

In my experience, there are a few key obstacles:

  1. We are afraid of failing – As soon as we think of an idea, we remember another crazy idea we had that didn’t work out. Maybe we remember a class project that got ridiculed in school, or we remember an idea we shared with our boss that got shot down, but whatever the case may be, we remember the pain of failure and decide it’s not worth the risk of feeling that way again.
  2. We are afraid of succeeding – This goes hand in hand with fear of failure. We think about what it would be like if we did change jobs or started a business. We get an image in our heads of how our lives might change and how those around us might change and we get scared. “What if I achieve all of this, then what? Who will I become if I get my dreams and what if I lose it once I’ve gotten it? What will my friends, my family, and my partner think about me? Will they still love me?” We get caught up in the fear of how much things might change if we succeed and we stop ourselves before we even get started.
  3. We don’t get started – Sometimes we have a great idea of what it could look like someday, but we have no idea of where to begin. The vision we imagine is so different from our lives now that the pathway from where we are to where we want to go is so foggy that we just quit instead of taking the time to really think about what that first step might be and actually take it.
  4. We get overwhelmed – Other times we know exactly where to start, but as soon as we think about all the steps between here and there we start to feel afraid. There are some obstacles two to three down the road that feel IMPOSSIBLE to overcome and so we think, “why even bother getting started if I’m not going to make it anyway.”
  5. We tell ourselves someday – Sometimes we make a plan for getting a dream job or starting a new business, but it doesn’t quite feel like the right time so we put it off. We tell ourselves someday and just like a gym membership that you pay for but never use, we use that feeling of possibility to satisfy our desire even though we never go after what we really want.
  6. We let other people discourage us – Sometimes we share our ideas with other people, but not the right ones and these people tell us our ideas are dumb. They aren’t the kind of people that honor our desire and help us come up with new ideas or help us modify our ideas into workable concepts, instead they just shoot us down in a way that makes us question our very ability to come up with ideas. On some level we know we could challenge them, but instead we choose to believe they’re right and so we don’t pursue our ideas any further.


These are things we ALL do. There is not a single person that hasn’t let an idea die because of something on this list. No one is immune, certainly not me and certainly not anyone I know.

So what can we do about this? Well it turns out there are a few key tools and tactics that can have a big effect on our ability to overcome these obstacles. Here are some of the things I’ve found helpful –

Overcoming the Obstacles to Creating Amazing Things

If you want to start your own business, get your dream job, or even bring your brilliant ideas into your current company, here are some things I’ve found really powerful in helping you overcome fear, work on your ideas, and turn your visions into a reality.

  1. Put things through the three question test on risk
    1. First ask yourself what is the best thing that could possibly happen – This question allows you to look at the upside of any action or course of actions you might take. It helps you get clear on the benefit of what you’re thinking about doing.
    2. Next ask yourself what is the worst thing that could happen – This question is really about noticing and owning your fear as well as considering the danger involved. Although embarrassing yourself might feel as bad as death, when you look at it directly you might realize that the downside isn’t that bad after all. You might also realize the potential downside is too scary to overcome and adjust your plans accordingly.
    3. Finally ask yourself what is the most likely thing that will happen – This question is all about looking at what’s real. We tend to get caught between the poles of wild success and total catastrophe even though usually reality is somewhere in between. This question helps you get a clear sense of what’s really going on and can help you get clear on what you want to do.
      Once you’ve looked at these questions you’re ready to make a choice. A couple questions to consider as you do this are:

      1. Am I willing to accept the worst possible thing? If the answer is yes then it’s likely worth the risk. If the answer is NO, then you need to look at how you can mitigate that risk before moving forward.
      2. Is the likely thing closer to your success answer than your failure answer? If the answer is yes then you have a better than average chance of achieving some part of what you’re aiming at. If the answer is no, you have to ask yourself why that’s the case? And is the payoff worth the high risk that you might fail?
  2. Assume Success – We tend to focus on how things won’t work. The reason why most people fail when it comes to looking for a new job or starting a new business is because the possible fail points add up and they become paralyzed. Which is why once you’ve decided to do something, you next need to assume you’ll be successful and ask if I was successful how would that happen? This question focuses your mind on looking for the factors that will lead to your success instead of obsessing about potential problems. It also helps you identify the framework you need to create the outcome you’re looking for.
  3. Identify Friction Points – Next once you’ve assumed success, you need to identify anything that might stand in your way internally or externally and come up with a plan to deal with them. Let’s say for example: you know that you often start things but have a hard time following through after the first few steps. You might make a plan to work with an accountability buddy who can help you move beyond your first few steps. Or it might be that you want to start a business, but you know that having enough money might be a factor, you might make a plan to stop going out to eat for a month so you can put enough money aside to make a small investment into your dream. By being honest about the obstacles you might face and planning for them, you’ll reduce the chance you’ll get derailed by them.
  4. Find Community – After you’ve thought about what you want to do, it’s important that you find some community who will support you as you go along. Maybe it’s a few good friends whose support you ask for as you move forward. Maybe it’s an online facebook group you join. Or maybe you might form a mastermind group of fellow employees or entrepreneurs that are on the same mission as you. The form of the community doesn’t matter as much as knowing you have people to go to for support. If you can, I’d highly encourage you tell them about the job hunt you’re undertaking, the business you want to build, or the initiative you want to create at your current company as well as the steps you’ve planned thus far. This way they will know exactly what you want to do and they might even have a few ideas of how they can support. In addition, you might let them know the kind of support that works best for you, if you know what that is. If you need people to bounce ideas off of, start there. If you need people to hold you accountable then ask for that. The more information you can give to people about how to best support you the more likely it is that they will take action to do just that.
  5. Focus on Step One – My friend and Aikido Master Izzy always says Step Two is where ideas go to die. The reality is when it comes to creating or looking for a new job, starting a new business, or creating your dream job at your current company you don’t need to worry too much about step two and step three. Especially if those steps are unclear or really scary. Instead, if you can get yourself to do step one and focus fully on that, you’re going to be better off. Planning is a great way to think through a process, but action is always one step at a time, so if you find yourself getting stuck or unsure of how to start, just focus on one small step at a time.
  6. Let Go of the Outcome – While it’s a good idea to start with a clear vision in mind, it’s easy to get caught up in that vision and lose sight of why you’re doing this. Remember this process is about discovering or creating a career or job that works for you. This is a process of discovery not perfection so whenever possible let go of what it’s supposed to look like and instead focus on how you’re showing up to this process. Maybe your dream job or amazing business will end up looking totally different from what you thought it would. This was the case for me, but I’m so glad I kept showing up and focusing on the intention I had when I got started. I knew I wanted to do something that served others in a really fundamental way and so even though my first few ideas didn’t work out, I just kept looking for ways to lean into my mission, which is how I ended up creating the business and life I’m living now.
  7. Keep Going – If all else fails or you suffer setbacks, just remember to keep going. It can feel scary and hard to go after your dream job or create your dream company, but the #1 reason most people fail to find and do work that lights them up is because they give up too soon. Most of the people I know that are doing amazing things just keep trying stuff until they found something that worked for them. This is certainly true for me and I can tell you it wasn’t always easy to keep at it. But having said that, I’m glad I didn’t give up. Even though I’ve had over 30 different jobs, I don’t regret all the time I spent searching for the work I love, because now that I’ve found it, it makes all of that hard stuff totally worth it.

I hope that you find these steps useful because they are some of the simplest and most powerful things I’ve used to go after my dream jobs and start businesses that I love. Not only have these tools helped me create the career I’m in now, they’ve also led me to some of the crucial stepping stones that prepared me for the amazing work I’ve ended up doing. Without these tools I never would have gotten to tour with a rock band, live in a monastery, or experience some of the other cool things that have made me the person I am now.

I wish I could tell you the path to your dream job will be nice a straight, but of course that’s rarely the case. But what I can tell you is that if you’re willing to keep pursuing your crazy ideas and following your curiosity, you’ll be amazed at where your quirkiness can lead you.


I want to give a special thanks to Leo Babauta of Zen Habits, and Charlie Gilkey of Productive Flourishing for some of the ideas and inspiration behind this post.