5 Hats You Need to Wear to Crush Your Entrepreneurial Goals
By: Katie E. Lawrence
Tags: Business, Entrepreneurship, Productivity, Startup, Technology

5 Hats You Need to Wear to Crush Your Entrepreneurial Goals

Focusing too intently might be ruining your productivity.

Photo by Austin Distel on Unsplash

Let’s be real y’all — being an entrepreneur isn’t always what it’s cracked up to be. As Thomas Frank pointed out in his recent YouTube video, 5 Things I’d Tell My 19-Year-Old Self About Running a Business, every entrepreneur has to wear several hats. Whether that’s shifting between creative and managerial tasks, or something completely different, every business owner/entrepreneur/self-employed individual different modes of working.

After recently starting a blog, I’ve felt this on all sides. Not only are we responsible for the upkeep and layout of our website, but we’re also responsible for managing our social media, responding to people’s questions and comments, and let’s not forget actually writing the blog.

“mode”, noun, a way or manner in which something occurs or is experienced, expressed, or done.

What’s important is that we try to shift through different modes on purpose. This list of the five modes of entrepreneurship is meant to help you do that. It’s meant not only to remind you of your responsibilities towards yourself and your business but of the different modes, you have the opportunity to flip between to be the most effective and happy.

1. The exploration hat

The exploration mode is the mode that every future entrepreneur goes through before they even decide what they’re going to try doing with their life. In the exploration mode, an individual will think of ideas. They’ll lay down before they fall asleep every night and think about all of the things they want to do, all of the places they want to go, the person they want to be and the things they want to create.

“explore”, verb, inquire into or discuss (a subject or issue) in detail.

In the exploration mode, the creator must let themself think and dream and feel without a filter. You must not control what is going through or prevent something from passing through your mind. Anything goes. Let it through, let it pass, or let it stick. Don’t lock yourself down on a particular idea — open yourself up to a vast array of possibilities.

For my own business and entrepreneurial pursuits, I’ll often put this down in my calendar as “tinkering time”. This is what Barbara Oakley, author of A Mind For Numbers, refers to as diffused thinking, as opposed to the productive focused thinking. Exploration mode is where it all begins — which kind of makes it the most important. If it’s not where you start, if it’s not where you begin, then everything you produce can still be good, but it will miss a key ingredient — unbridled creativity.

2. The brainstorming hat

Now you have your ideas. Once you have your ideas, your unbridled and unfiltered list of things you’ve come up with, you have to get into actionable steps. Now that you’ve decided what your options are, you have to pick something. The brainstorming mode isn’t as much of a creative process, but a revisionary process. Once you have your ideas, you have to decide which you are going to use in your life/business/etc.

Whether it be throwing your ideas out on Reddit (my favorite pass-time) and waiting for feedback or talking with a few friends on Skype, get your ideas out into the world in a brainstorming and experiential way.

“brainstorming”, noun, group discussion to produce ideas or solve problems.

But, as you can see in the definition of brainstorming brought to us by Google, brainstorming is about more than just yourself. When you have a brainstorm, you have to have a whirlwind of brains, plural. We often mistake brainstorming for sitting in our room by ourselves — but that’s just thinking, maybe it’s idea generation.

“You can’t use up creativity. The more you use, the more you have.” — Maya Angelou

To truly brainstorm, you have to work with other people. Whether it be throwing your ideas out on Reddit and waiting for feedback or talking with a few friends on Skype, get your ideas out into the world in a brainstorming and experiential way. I’ve talked with friends over the phone, co-workers over Zoom, and family at the dining table and come up with more ideas than I ever could on my own. When you have your idea and are ready to get to work, don’t forget to bring your crew together and get some ideas.

This is also the mode where you’re researching, reading articles, books, etc. on what you’re looking into as a potential idea to proceed on. And if you don’t have anybody to brainstorm with about your ideas, write a letter to yourself. In brainstorming mode, your mind is testing out ideas, deciding how to proceed.

3. The monk hat

Monk mode is the third mode and it builds off of the results of your two previous modes. Once you have your ideas, and once you’ve filtered those ideas through your mind and the minds of others, you have to apply them to your life and your model of business.

“A monk may be a person who decides to dedicate his life to serving all other living beings, or to be an ascetic who voluntarily chooses to leave mainstream society and live his or her life in prayer and contemplation. The concept is ancient and can be seen in many religions and in philosophy.” (“Monk”, from Wikipedia)

In her TED talk, “Want to be more creative? Go for a walk”, Marilly Oppezzo talks about something called “appropriate novelty”. Creative ideas can come from anywhere, but they must be practical.

“Monk mode will increase your resilience and independence. If you were able to cut people and pastimes from your life, what does it say about you?” — Lucio Buffalmano

The monk mode of the entrepreneur’s creative process is the most spiritual and introspective of the modes. In the monk mode, an artist is focused on what is most important for their life, mission, and goals right now. I write often about my commitments list, but there’s another thing that I use to postpone my goals and dreams. I have a chart with a timeline for the next eleven years of my life.

“I plan to live a few months in San Diego, I plan to pursue a certain career, I want to join a climbing gym. These three goals, among the dozens of other goals I have in this chart and in my head, are no less real or exciting to me as those I’m pursuing now. They’re simply not those I’m ready to pursue. I have intuited and factually know that the time is not right.” (From my 2019 personal journal)

I figured that out in monk mode. Monk mode is when we can journal, when we can process where we are, get in touch with how we’re feeling and who we need to be, and what we need to be pursuing to keep ourselves interested and passionate about the work that we’re doing.

4. The grinding/working hat

Now you’ve thought of ideas, you’ve filtered the ideas, and you’ve ideologically processed them, now you’re ready to work through those tasks — and once you’re done, you’re going to see the results. This is often our least favorite mode, but it can be one of the most important ones. It becomes especially productive when you invite creativity into it. [“grind”, noun, hard dull work.]

“Greatness is sifted through the grind, therefore don’t despise the hard work now for surely it will be worth it in the end.” ― Sanjo Jendayi

This is that 4-hour block of time you’ll spend designing your website or the 10-hour day you’ll spend rounding up a list of clients who might actually be willing to speak to you. It’s the weekend you spend in constant writing mode, or the endless research hole you go down into for your next piece.

This is where the real work happens — and you’re prepared for it. Don’t forget to grind. Otherwise, everything else you’ve done in preparation for your work is kind of a moot point. This is where I will put about a five-hour block of time into my calendar where I’ll go either to a quiet coffee shop, the library or somewhere else I know I won’t be disturbed.

5. The executing hat

In this mode, you have to use your executive functions to say “yes” to the things you need to say “yes” to and “no” to the things that you need to prevent from cluttering your schedule at the current time in your career path/year/etc. [“execute”, verb, carry out, or put into effect (a plan, order, or course of action).]

Executing mode is all about taking your ideas that align with your current stage of life and your current goals, and making them happen. In executing mode, you’re emailing people, you’re making phone calls, you’re filling out your calendar, creating a clear and actionable task list, and preparing to sit down and work.

Not only are we responsible for the upkeep and layout of our website, but we’re also responsible for managing our social media, responding to people’s questions and comments, and let’s not forget actually writing the blog.

For me, executing mode is when I’m finally able to check off my task. It’s where I finally hit send on the email, or add the meeting I wanted to schedule to my calendar, buy the product/membership, and more.

Execution mode is all about getting balls rolling, whether that be planning for you to do the work or delegating to someone else. This is where stuff gets done. Save this mode for when you’re brave enough to really do something. This is when you buy the domain name, publish the blog, outline the next post. When you finish in this mode, the task is complete, the plan has been executed, and it’s time to move onto the next amazing project.