Favorite Business Hats of 30 Entrepreneurs

Whether you are a brand new start-up or solo entrepreneur, you know that the buck stops with you — meaning you have many hats to wear each and every day. Of those hats, there are ones you enjoy more than others, and ones you work hard to let someone else wear as soon as it is financially possible.

One of my favorite hats to wear is that of the Connector. When on my head, I have the pleasure of meeting and greeting new people on and offline, as well as making connections among those with whom I interact. Knowing how much fun I have in that part of my business, I wanted to hear from you and asked –

Since you must wear many hats in business as an entrepreneur, which one is your FAVORITE and what makes it so much fun to put on?

Thirty of my wonderful Question of the Week contributors rolled up their sleeves and shared their stories this week. These talented business owners love wearing hats for creativity, speaking, strategizing and more. The award for the “hat” that made me laugh out loud goes to Dr. Barnsley Brown for her GBK hat. Love it! Enjoy!

1. The GBK Hat Rules!

The GBK (Gentle Butt Kicker) Hat is a pleasure to wear since I get to help motivate people and organizations to reduce stress and create more time, energy, and money in their lives right now! All the great content in the world means nothing if it’s not backed up by action, so I always wear the GBK Hat to help my clients get real results. The GBK Hat is the one that motivates ME to wear all the other hats: the marketing hat, the customer service hat, the product creation hat, the coach and speaker hat, the mompreneur hat, the list goes on and on. So the GBK hat also kicks my derriere too, in a totally positive way!

Thanks to Dr. Barnsley Brown of Spirited Solutions Speaking & Coaching

2. Be A Booth Babe!

Nobody would ever mistake me for a trade show ‘booth babe’ but representing my firm at trade shows is my favorite ‘hat’ to wear. In my business (iPhone apps) I have very little live customer interaction, so trade shows are a great opportunity to both meet prospects and customers and get interactive feedback. Trade shows are also a chance to check out the competition.

Thanks to Todd Bernhard of No Tie LLC

3. Blogger Is My Favorite Hat

I’m a verbal processor. To me, that means I work and feel best when I can talk out loud about something or when I can write about it. I prefer writing, because I can go deeper when I want to and while I process, I’m not seeing how you’re reacting to what I say. So it is possibly a more honest expression. It’s a solitary experience while it’s happening, which I love. And when the writing is shared, it’s an experience of community. Whether people comment or not, the blog is shared widely. Blogging allows me to tap into my creativity and wisdom and lets me share it with many people at a time. This career as an organizing coach is my second career which allows me to give back, important at this stage of life and wisdom.

Thanks to Sue West of Space4U Organizing & Coaching

4. My Favorite Hat Is “Business Strategizer”

I believe so many business owners are so busy doing the daily task to run their business that they don’t take time out of the business to work on the business. I set time in my schedule each week that I could not be interrupted. That time was used solely to determine the changes that needed to be made to bring the business to “the next level” and the time line and allocation of duties to get it done as efficiently and effectively as possible. It could be to upgrade a system we have been using for years, hire and train new staff, bring in new technology, develop and implement a marketing plan and so much more. This is what truly made the difference in building the business from scratch to the very successful business it became.

Thanks to Nancy Butler, CFP®, CDFA™, CLTC of Above All Else, Success In Life And Business

5. I Like To Sport The PR Hat!

My favorite role in the entrepreneur journey is Public Relations. I like everything that is concerned with the image of the company! I love to focus on social media, media relations and customer service. I know accounting, sales, manufacturing and general logistics also require attention. I try to balance my hats the best I can but if I could, I would wear the PR hat all day long!

Thanks to Christy Cook of Teach My

6. Speaking To Groups

My favorite hat is Speaker. Although many hate getting up and talking – I love the opportunity to empower other people to do one simple thing. I also love the interaction with the audience and take note of the questions. It gives me a better idea of what questions business owners have, gives me ideas for my Tip of the Week, and gets me consulting appointments as well as website clients. Speaking has been the single most responsive lead generator I have tried.

Thanks to Dotty Scott of Premium Websites, LLC

7. I Love Getting Paid To Talk On The Phone

A lot of my work is consulting over the phone or Skype–on effective marketing, book publishing, and going green/marketing green. I love this. I get to give powerful advice that turns into profits for my clients–and I get to do it, if the weather is nice, from my deck overlooking the mountain and the farm I live on. I like the writing assignments too, but consulting doesn’t strain my eyes or my hand tendons.

Thanks to Shel Horowitz of Green And Profitable

8. Favorite Hat? What Time Is It?

Until I was 40, I thought I was mentally ill. I thought this because I had so many interests, had so many learned skills and natural talent and usually tried to satisfy them all – all the time. I was told over and again that I just needed to focus. Focus to me meant being strangled and cut off from what made me thrive and alive. I could find synergy between the most disparate things! So then I learned the real secret – be in a project that is so big it is a necessity to utilize ALL of your skills and talents every day. Whew! What a relief. Favorite hat? What time of what day of what month are you asking about? PS: over the last few years I realized there is a name for my mental illness – it is called entrepreneurship. LOL.

Thanks to Linda Hughes of Entrepreneur Community Online, LLC

9. The Strategist Hat

I guess I am a like a general. I like to bring all the parts together and see how they can move things forward, overcome obstacles and most of all create opportunities where others don’t see them. It’s like a game, which is I guess why that hat is so much fun.

Thanks to David Leonhardt of THGM SEO Marketing

10. It’s The Creativity

In my PR business, my favorite “hat” is that of the creative strategist. That is why I deliberately kept my company small. I recognized early on that when you own a large firm, you function primarily on the business side, not the creative side. The creative work is where my heart lies.

Thanks to Jane Blume of Desert Sky Communications

11. From A Spark To Flame

My favorite hat to sport in my business is that of CTO. I get to manage a team of programmers overseas and pump out awesome features on our site through code. It’s a truly rewarding experience seeing my ideas come to a successful fruition digitally for the world to see.

Thanks to Dahlia Roth of GovernmentBargains.com

12. What Is Your Favorite Hat?

Most of the hats I need to wear in order to run the company are enjoyable. Hands down my favorite relates to the creative process. Recognizing an artisan with skills, applying them to a contemporary design, watching the product find its way in the market and having it afford that artisan a way to earn a living, simultaneously preserving the craft. It is a challenge every time and one that I love.

Thanks to Isabel Garreton of Isabel Garreton, Inc.

13. Making Those Deals!

If there is one business hat that I enjoy wearing the most then it has to be the dealmaker hat. I love making the deals with the various companies that are now dying to work with us giving things away through our site and Facebook page. It’s a great feeling successfully bringing in company after company to work alongside us.

Thanks to I. Aronovich of Awardable

14. The Hat Of Public Relations

The business hat that I love to wear the most is that of a public relations manager. I love pitching stories to reporters and responding to the media via phone and emails. I get immense pleasure from helping to get our company’s name in print and pixels all the time!

Thanks to Michael Pesochinsky of GovernmentAuctions.org

15. Making Lights Go On

I love sharing new ideas and insights with people! I don’t think of it as selling, but as exploring new options. There is so much new information, there are so many new ways of thinking about things, and so many insights that can make a difference, that I LOVE engaging people in seeing how they can benefit from all this newness.

I’m a teacher by disposition, so sharing comes natural. When my clients make new connections and see how they can expand their capacity, create new products or open new markets, or even rethink their business, I get excited along with them!

Thanks to Kathryn Alexander of Ethical Impact L3C

16. A Hat Of Deals!

The business hat that fits the best on me is that of a deal-sourcer. I love actually scouring the Internet for the best deals every day. It’s like hunting for some rare beast that I’ll use to feed the hungry citizens with the best possible savings you can find each and every day.

Thanks to Elik Aaron of SaleRacks

17. A Hat For A Home

The customer service hat is the one I truly love wearing the most. I love to help that person on the other side of the email or a telephone find a good piece of property for his or her family. It feels great that I’m helping people find a place that they can call home.

Thanks to Eli Israel of Foreclosure Magic

18. Creativity Is Queen

As a solopreneur I’m constantly juggling many hats. Depending on the day and time, certain ones will always have to take precedence, but the one that I always look forward to wearing is that of ‘Creative Director’. This is where I get to think outside the box and create workable solutions to problems that may have arisen for my clients. I’m like a kid in a candy store as I work an idea from its infancy through solution. The added joy is seeing the relief of my client once the solution has been implemented.

Thanks to Barbara Goldberg of Back On Track Solutions

19. Creativity / Content Manager

What I love most about my business is the creativity involved in producing content for my blog posts, training videos, e-zine, and live workshops and presentations. There is something magical about expressing thoughts and giving advice in a manner that resonates with people and that is memorable. It involves both selecting the words and sequence to deliver a story and selecting the images that reinforce the message. I often find myself “in the zone” when I am creating content – time seems to melt away and I can buzz along for hours without realizing it. Perhaps I’ll find that “sweet spot” with other business activities someday!

Thanks to Monique Y. Wells of Understanding Time Management

20. Expo Fun!

I love to do Expos. I think because it is a part of the business that is a little different every time. It’s fun to come up with the decorations for the table, the layout of the products, and the cute something special to draw people to your table. At our last expo, we came up with a Mascot to go along with the theme and cover of our new book. The giveaway snacks even went with the theme! If you are having fun, people want to come to your table and find out what you are up to. It was so much fun!

Thanks to Sally Vickers of Team Powered Success

21. Creative Bliss

My favourite hat is generating the ideas that will create the change the business requires. From identifying what the true target is (not usually the most obvious one) to developing a strategy that will bring that target to fruition and creating all of the elements that actually make it work. I draw possible solutions from everywhere and my brain works whole-brain (i.e. autistic) so it truly is a fun experience for me and my client.

Thanks to Lisa Murray of Revive Business Coaching

22. Make Way For The Young Folks

My favorite entrepreneurial hat is guest speaker at youth events. There’s something about talking to young people who gets me excited and motivated. Young people have this wide-eyed innocence and they are so hungry for answers. I love telling them my experiences growing up and the pitfalls of growing up in the inner city. I always start off with a questions when I come into a room to get them started this makes for great dialogue and discussion. This is my favorite hat to wear.

Thanks to Eula M. Young of Griot’s Roll Film Production & Services Inc.

23. Brainstorming Delight

What I love the most about my coaching work is the opportunity to do creative brainstorming with others. Starting with the assumption of “no limits” and letting ideas flow and percolate and bounce off each other and expand– is a delightful experience. The “aha” moments are energizing. Given enough time this creative exploring leads to new ideas and new directions and there is always some thread that can be worked with in a very tangible way.

Thanks to Maureen Daniek of Radiance Coaching And Consulting

24. Catching A Fish

Unless I need to make an impression, I LOVE playing the layback, simple, joking around kind of person. People in business translate that into “He’s easy to get over on”

My sons would say “You think you’re getting over on him, while all the time he is drawing circles around you. He is miles down the road waiting for you to get there”

It’s a lot of fun. There’s no reason to ever show being clever or shrewd. I always let the other one do most of the talking. If a person was honest with me, I reciprocated. People trying to ‘get over’ or ‘sell’ you, usually do a lot of talking. It’s interesting just laying back & listening. You learn a lot about them & what it is they’re trying to get from you. Without them realizing it, in a quiet simple way you gain the advantage and you “Caught a Fish!

Thanks to Harris Glasser of Serving The People Press LLC

25. Creativity Is Where It’s At!

My favorite part of my business is creativity and idea-generation. I love curling up with a pencil and sketch pad to draft new design or business ideas. It’s the making something out of nothing that I really enjoy.

Thanks to Barbara Austin of Sweet Dreamz Design

26. Put Me On Stage So I Can Shine!

My favorite business hat is when I get to be the speaker in front of a group of people. That’s when I get to connect my message with the most power and impact to many people at once. It also gives them the best chance to see me for who I am… to build the know, like and trust factor on the spot.

Since their attention is on me for the duration, their focus can be kept on what I’m sharing and not be lost in a sea of emails, Facebook posts etc. The connection that’s established is so direct and intense that it can move people to take decisive action right away.

p.s. I was a shy kid who never would’ve dreamt of doing this but thanks to many years in theatre I now relish every chance to get out there and speak. The power of spreading your message in person is so empowering and such a rush!

Thanks to John Rasiej of Speak Louder Than Words

27. I Am A Contender And I Am Somebody!

I think my favourite role is that of being creative in a field I once thought was dominated by the “Samantha Jones'” of the world! I can do my own PR and marketing which is a million miles away from programming a database. I even find myself dressing in a more “fun” way when I’m working on this because of the stereotype I have in my head of a woman in marketing! I feel as though I’m playing a totally different character and Marlon Brando has nothing on me!

Thanks to Alexandra Sheach of Mosedale Consulting

28. Livin’ The Dream

While the entrepreneur has an endless list of hats to wear, each with its own mountain of responsibilities, by far the “dream realized” hat is the best. Getting up every day knowing you are living out your dream, the vision you had from childhood, the goal you put your heart and soul on the line for, is now what plays a part in the story of your life. Your mission is now serving a greater purpose than just filling up your imagination. It is a feeling that is undeniable and so powerful that it drives a 90 hour work week, propels you from “what if” to “all in” and validates the idea that once only occupied the space between your ears. The work ethic, communication and negotiating skills needed may not be as fun, but to take that chance and live a dream is more than worth the effort.

Thanks to Lori Sica of NJ Greats

29. Oh, I Know This!

My favorite hat to wear as an entrepreneur is when I get called upon to be an expert.

When I was a kid, I was, and still am, a know it all. Merciless teasing by family and friends taught me to recognize that, that particular trait can be annoying, if used too much. Now, as an expert in my field, I get to use it appropriately.

So when I am asked to speak or write an article, or share a quote, it’s a win-win situation. I feel acknowledged and my audience gains some knowledge.

I worked hard to get here.

Thanks to Miriam Ortiz Y Pino of More than Organized

30. Wear All Your “Hats” With A Positive Attitude

Owners of small business wear a multitude of hats out of necessity. I think it’s important that no matter what the “hat of the day” is, it needs to be worn with a positive attitude. Henry Ford was quoted to say “If you think you can do a thing or think you can’t do a thing….You’re right.”
Speak highly of yourself and believe in your dreams; if you are passionate and genuine, others will notice and get behind you, bringing recognition to your leadership.
Linda Hughes of ECOnline shared this statement with me and it personifies positive attitude “Leaders are visionaries with a poorly developed sense of fear and no concept of the odds against them.” – Robert Jarvik

Thanks to Chris Hollerback of TCFS Development Co. LLC

Thanks so much again to all our wonderful contributors for sharing your favorite business hat! We hope to hear from you again. And to all our readers, if you have an innovative idea to share, we hope you will leave it in the comments below.


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  1. Posted May 22, 2012 at 6:38 pm | Permalink | Reply

    I love my educating hat!
    I can proudly say that I love educating general public as well as my clients as to all important and relevant real estate information, so that can make an informative and intelligent decision regarding investing in real estate, whether it’s they primary residence or investment property.

    • Posted May 23, 2012 at 5:48 am | Permalink | Reply

      Andrey, Thanks for sharing your hat! Educating others can be so rewarding, especially when they reap big benefits as a result. 🙂 Shannon

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