24 Entrepreneurs Share Ideas on How to Think Outside The Box

Want to be a think tank in your business? Well, it’s not always natural or easy to be creative and think outside the box as a business owner due to fear of risk-taking, desire for perfection and clinging on to old ways of doing things. So how do you ignite your creative self and foster that in your team? It’s not necessarily hard and can be achieved.

We asked entrepreneurs and business owners how they think outside the box and here are the insightful responses.

#1- Create increasingly restrictive parameters

Photo Credit: Sam Olmsted

The easiest way to force yourself to think outside of the box is to create increasingly restrictive parameters around a situation and see how your thinking changes with each new scenario. For example, let's imagine you need to find new marketing solutions with a tight budget. First, try thinking of how you would achieve the goal with no budget. What are the types of solutions you could come up with? How would your limited budget then bolster this zero-budget solution? By restricting your resources, you can actually get more creative and find new ways to solve problems.

Thanks to Sam Olmsted, Online Optimism!

#2- Getting a fresh look

Photo Credit: Joe Terrell

Being surrounded by people from my industry is not always beneficial for out-of-the-box thinking as I am aware of a tunneling vision that restricts the horizons of creative thinking. That's why when I am looking for some non-standard solution, I try to talk to some friend, or a stranger in Social media who is not involved in business and my sphere asking them about some pain points that may have or trying to explain to them what I am doing in the context of a chat. Such conversations are so insightful and motivating, they help me to see the problem on a completely different angle, and usually, here's where the best non-standard solutions come from.

Thanks to Joe Terrell, Drifted!

#3- Studying practices and techniques

Photo Credit: Daivat Dholakia

I think outside the box by studying practices and techniques employed by businesses in other industries. There's a lot you can learn when you look outside of your niche! Instead of focusing 100% of my attention on what other fleet management services or app developers are doing, I broaden my outlook. What's going on in the different sectors within the auto industry? What's going on in AI development? You can learn a lot from businesses in other spheres–there's no reason to be limited by following the guidelines set by your main competitors, and that certainly won't help you outcompete them.

Thanks to Daivat Dholakia, Force by Mojio!

#4- Exploring Opposing views

Photo Credit: Damien Knight

I think out of the box by exploring opposing views. Exploring a problem from the other side of the argument is a perfect way to think beyond the box and works perfectly great for me. I used to assume that my responses to a situation are reasonable and objective. Some individuals, on the other hand, may have legitimate counter-arguments. As a result, I came to know that it is beneficial to pay attention to opposing viewpoints and beliefs. Those contrary perspectives don't always affect my action. I may also be able to point out flaws and quality in them, which is a great place to start. The aim is to explore all potential solutions to a problem before settling on the best one.

Thanks to Damien Knight, Workever!

#5- Literally getting outside the box

Photo Credit: Melissa Kelly

I spend so much time cooped up in my little apartment, and staring at the computer screen. In order to spur creativity I try to get outside. I may go for a 30 minutes walk, or out on my bike. I find this time out and about is great for thinking outside of the box. I would attribute this success to two areas. First, exercise is proving to stimulate brain activity because you get your blood flowing. Second, I am exposed to new ideas outside. For example, I once saw a billboard advertising some food product that gave me an idea for a campaign to run for our business. The point is that your home is a box, and you can literally get outside of it.

Thanks to Melissa Kelly, Virtual Team Building!

#6- Tactical approach

Photo Credit: Nicolas Gagné

My approach to thinking out of the box is somewhat tactical. The first step is to understand what my box truly is. It's probably different (although maybe similar to) anyone else's box. Then I write about it, paint it, describe it as fully as I can, knowing it is a metaphor for this next part: What are my limiting beliefs? After that, I begin with a perspective that, by definition, doesn't make sense within my existing paradigm (box). I pick opinions opposed to mine and start arguing for them as if they really were my views. Then I extract an attribute or direction of thinking from that starting point and link it to what I already know. This linkage usually opens up new perspectives or directions of thinking that I would otherwise be unlikely to take. I choose this approach because it helps me realize that everything we think we know is merely an abstraction, an over-simplified symbolic representation of what really is there. If we're attached to our ideas being correct or representing a reality, we'll never make it out of the box we're in.

Thanks to Nicolas Gagné, Win In Health!

#7- Starts by not shutting anything down

Photo Credit: Ravi Parikh

For me, I work really well when I bounce things off of others. I have people that I riff with really well and are my go-to brainstorming buddies — it has to do with their ability to be silly and leave judgment at the door. And there is also a level of comfort and trust that we all have built over time. There are moments where we just go down a path that has us in stitches and we aren't taking anything seriously but then all of a sudden out of that nonsense there is a bit of magic that forms and we will then finesse an idea until it is fully formed and functional, although rooted in madness.

Thanks to Ravi Parikh, RoverPass!

#8- Challenging assumptions

Photo Credit: Edward Shaw

I’ve read once that it takes only about 50 milliseconds to form an opinion about something or someone. Of course, you need to be assertive in the business world and able to make quick decisions, but sometimes admitting you are not right is the most difficult thing. If there is no evidence to your assumption, it is just that – an assumption. Let me give you an example. Say you wish to organize a party and invite your friends. One would assume the best way to do that is via Facebook, where in reality not everyone you want to invite has access to it. By challenging this assumption, you can easily realize that phoning or texting someone is much more personal and intimate. This results in an increased chance of the person showing up! Assumptions restrict your thinking. When you assume something, you deny progress and limit yourself.

Thanks to Edward Shaw, LeelineSourcing!

#9- Leveraging disruptions

Photo Credit: Matthew Allen

One important way you can think outside the box is by figuring out ways to leverage disruptions to your industry and turn them into competitive advantages. When a wrench is thrown in your plans, step back and think about it from a high-level viewpoint. Maybe this disruption can even benefit your business. Think about how you can pivot and adapt in a clever way that your competition won't think of. While they are scrambling to mitigate the industry disruption, you are converting the disruption into a competitive advantage to rise above your competition.

Thanks to Matthew Allen, AmaLinks Pro!

#10- Outsourcing to other industries

Photo Credit: Gerald Lombardo

I outsource to people I know in other industries with other backgrounds. In order to think outside the box, I have to pull away from what I have come to know as comfortable and normal and indulge in the unfamiliar. I brainstorm with colleagues that can give me insight from a different approach so I land at a unique destination. I find this process stimulates creativity and unique perspective that I would not be able to piece together with my own knowledge.

Thanks to Gerald Lombardo, The Word Counter!

#11- Eliminate the box

Photo Credit: Desiree' Stapleton

We've been conditioned to do things how everyone else sees fit and sometimes what works for one person, doesn't work for another. I learned that the biggest way to add value to people is to show up as your authentic self and serve the heck out of them. It's okay to acknowledge that there are pre-made parameters to things, but you are _allowed _to put your spin on it. Those that do are the ones that get noticed. The lid is off and the door is open. Step out. You have everything it takes to live the life that you envision, so eliminate that dang box! Whenever I feel like I'm stuck, I look for a different algorithm!

Thanks to Desiree' Stapleton

#12- Back to the basics

Photo Credit: Michael Hammelburger

I always go back to the basics: starting from scratch. And then I ask myself, What would I do differently if I were to start again? What would someone outside the organization think of this idea? How would my competitors react when they learn about this project or product? It's all about going back to a clean slate where the drawing board needs to be filled.

Thanks to Michael Hammelburger, The Bottom Line Group!

#13- Seeing the opposite

It sounds strange to say, but I like to play devil’s advocate when it comes to my thoughts. I think the exact opposite of what I was already thinking. Refuting my own thoughts allows me to find potential loopholes or flaws in my ideas, allowing me to expand on ideas or come up with new ones. It forces me to see the opposite will help you to open your mind to all possibilities.

Thanks to Scott Rosenberg, MaryRuth Organics LLC!

#14- Practicing meditation

Photo Credit: Olivia Young

I like to practice meditation. It not only quiets my mind, but also helps me notice the random thoughts that come in and out of my mind without me judging them. This allows me to come up with ideas for my business that I normally wouldn’t think of.

Thanks to Olivia Young, Conscious Items!

#15- Asking for a child’s opinion

Photo Credit: Guy Bar

As crazy as it sounds, children are often creative and think and speak in a way that goes outside the norm. You can ask them how they might work through a problem. If there isn’t a child around, I like to break down a problem so that a child could understand it.

Thanks to Guy Bar, Hyfit!

#16- Quiet walks and studying the world

Photo Credit: Derin Oyekan

I like going for quiet walks and studying the world around me. The best time to do this is usually the morning just as my brain is waking up. I’m able to process a lot more of what’s going on around me as well keep my mind open to everything happening.

Thanks to Derin Oyekan, Reel Paper!

#17- Considering a broader view

Because we humans are more so creatures of habit, we are hardwired to make decisions or think the way we do based on the life experiences that we're limited to. A helpful way that to think outside the box is to always look at the bigger picture of things, and take reasonable risks accordingly. Similar to thinking long-term with business ventures, looking at the bigger picture allows you to see ways in which processes can be improved for example, and is an approach that is driven from an optimist way of thinking. With a broader overview, you're also able to take more reasonably calculated risks which, in the larger scheme of things is a great way to learn from through experience.

Thanks to Zach Reece, Colony Roofers!

#18- Creating a collaborative culture

Photo Credit: Ella Jesmajian

By creating a collaborative culture, we are able to harness our creativity, expand on new ideas and assess each suggestion properly. If we decide to move forward with an idea, we create an action-based plan and timeline. This approach has worked well for us. It's also encouraged our team members to bring their ideas to the table and fight for their passion as well.

Thanks to Ella Jesmajian, Honey & Roses Coffee Co.!

#19- Getting into a creative space

Photo Credit: Josephine Walters

Thinking outside the box comes easy for me when I can get my mind into a creative space. To do this I need to be well-rested with a clear mind. Although I can do this at any time of day, my best out-of-the-box ideas usually come to me in bed, more specifically when I'm falling asleep or just waking up. That sweet spot between being completely asleep and awake is where the magic really happens for me. When I need to, I intentionally go to bed thinking about a problem I'd like to solve – It could be product design related or something entirely different. Then I drift off while thinking of (or visualizing) solutions, letting my brain create freely as I fall asleep.

Thanks to Josephine Walters, Noots Pets!

#20- Different point of views

Photo Credit: Adam Garcia

Brainstorming weird ideas, get that creative juices flowing. Look at things from a different perspective, take breaks while observing something helping you take a different approach. Ask for opinions, different points of views can certainly help in thinking outside the box. Imagine where you want your business to be in 5 years and come up with solutions as to how you can achieve your goals in your own unorthodox way.

Thanks to Adam Garcia, The Stock Dork!

#21- Visualization

As a business leader, I practice an innovation-centric mindset through visualization. I visualize how things are working now and how they can become even more efficient and productive for everyone in the workplace. To develop and expand a business further, I think outside the box by taking what we already have running now and scaling all the possibilities that it could be better by changing my perspective that it is already enough. I visualize things to be more, greater, and then create opportunities for those ideas and visions to be vetted and implemented.

Thanks to Stacey Kane, EasyMerchant!

#22- Knowledge of what's inside first

Photo Credit: Ofer Tirosh

To think outside the box, it is important that you know what’s inside of it first. Familiarize yourself with all the ideas and let yourself soak in all the wisdom there. After that, think about what’s missing and carefully go out of your box. Search for the things that could fill in the missing part by reading some books, watching movies, gazing at artworks, listening to music, scrolling through your feeds, walking out of the park, and eating foods. Enjoy your way out and you’ll eventually succeed in getting out of your box.

Thanks to Ofer Tirosh, Tomedes!

#23- Continous learning

Photo Credit; Andrew Winters

In order to think outside the box, the key is to never stop learning and exploring. In my free time, I like to try out new hobbies and learn about new topics. By learning about things outside of law, I am able to change my perspective over and over again. This helps me to stay creative, keep my brain active, and explore new ways of doing things. I have found masterclass and skillshare to be excellent ways of learning new skills without spending too much time or money.

Thanks to Andrew Winters, Cohen & Winters!

#24- Challenging what is possible

Photo Credit: Gretchen Halpin

As a parent and entrepreneur, I am regularly faced with the question of why? I've always pushed the envelope in everything that I do. So, when my business partner and I started Beyond AUM we extended the question of why into why not? Developing growth opportunities in the financial services industry may seem like a mundane task but when you apply the why not approach, we constantly challenge what is possible by providing room for the ideas to flow.

Thanks to Gretchen Halpin, Beyond AUM!

How do you think outside of the box? Tell us in the comments below. Don’t forget to join our #IamCEO Community.

Mercy - CBNation

This is a post from a CBNation writer. CBNation is a Business to Business (B2B) Brand focusing on increasing the visibility of and providing resources for CEOs, entrepreneurs and business owners. CBNation consists of blogs(, podcasts ( and videos ( CBNation is proudly powered by Blue 16 Media.

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