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Hats - Which One Am I Wearing Today? A Style Guide for the Many Hats of an Entrepreneur


As a solopreneur, not only are you on the job day in and day out, but you’re also a "Jack of all trades, master of none" - at least until you have the financial power to grow your most important asset, your team.


Being in charge and calling the shots might feel like an entrepreneur’s dream, but the ones who ace the demanding, multi-faceted role know a thing a or two about reality. The way David Evans describes entrepreneurship life in one of his Inc.com contributions stuck with me. He considers being an entrepreneur as having to sometimes “roll up your sleeves and make the shift from chief cook to bottle washer”. I couldn’t have said it better myself. 


Hats - Which one am I wearing Today? 

Looking at things from a quantitative & qualitative (I will address this later this month) perspective will be your barometer for answering some important questions beyond "Does this hat match my outfit?", like “When do I wear what hat?” or “How long should I keep my sales hat on?” The truth is, there’s no universal answer or recipe to the amount of time you will spend on each role. To get the right answer for your company, you need to take a closer look at your business plan. Analyze your aspirations and break them into smaller, actionable objectives over the month and quarter. If you need to gain 20 more clients by the end of the quarter, think about how many calls you should make, how long it will take to get each deal done, and then allocate that time to wearing your sales hat. It would help if you also kept in mind that your initial timelines won't be as accurate as you'd hoped. It is always good practice to add a buffer to your estimates.


Style is everything: Below is a collection of my favorite hats and a quick style guide on picking the right hat for the right 'occasion':\

  • The Product Hat: when starting your business, you have a vision. Thriving entrepreneurs use Design Thinking to shape their vision. With, Stanford's Design Thinking Bootleg, your product concept template is in check. When you are in the zone of Defining, Ideating, or Prototyping, you should be donning your Product Hat. 

  • The Sales Hat: At the core of every Sales Enablement program is 'Process'. You'll shift into your Sales Hat anytime you are considering how you will Attract, Onboard, Engage, and Retain prospects throughout the customer journey. If you are looking for recommendations on a blueprint for a strong and stylish Sales Hat, I love Salesforce's customer experience map, and wear it often.


  • The Marketing Hat: When your day turns to a clear agenda concentrated on Marketing Accepted Leads (MAL) and Marketing Qualified Leads (MQL), it's time to try on your Marketing Hat. Marketing is an art as much as it is a science, with a focus on garnering better connectivity to your customers. Take a moment to tune into Julia Goldfin, CMO of Lego, and her interview on youtube for some powerful digitally inspired content. You will quickly learn from Julia that at the heart of Lego's customer journey is a child's desire to learn. Knowing this helped Lego launch several Lego stories like "Lego Paris". In Julia's latest interview she said, "There isn't a formula, but it is around staying connected." If you are working on new ways of staying connected with your customer like Lego has, you will find your way with tools like B2B Marketing.


  • The Finance Hat: Arguably, finance is best learned on the job. Sure, the finance classes I took in grad school shaped my understanding of International Markets. However, I believe I may have learned more about finance when my business accounts were in the negative than any class could teach! Everything that happens in your business will ultimately be woven into your operating model. You are winning if you can land on a true Customer Acquisition Cost (CAC) within the first few months of operation. Below is a fairly common operating model used by Venture-backed early stage companies.

Entrepreneurs have a tendency to place the tasks they enjoy or feel they are good at as a high priority, and others as low priority. Whatever your perceived strengths and weaknesses, it’s important to keep a clear, objective mind. Be prepared to acknowledge that your business plan might require taking some of the hats that have been pushed to the back of your closet, dusting them off, and putting them on again.

“Growth, and new business, should always be the focus of the entrepreneur because if the business is not growing, it’s slowly dying.” (David Evans, The Many Hats of an Entrepreneur)

Your hat collection might be impressive, but it would be a fashion faux pas to wear them all at once. Multitasking and juggling different roles can be a productivity killer. Instead, focus on one role at a time, and give it your best. You might have to pause working on that sales pitch to join a hiring interview, or interrupt your financial analysis to talk to a vendor or a client.


Practicing mindfulness will teach you how to live in the now and be present, so when you’re wearing the marketing hat, you’ll be the best marketer you can be, but when you take it off and swap it for your snazzy finance hat, you’ll be 100% focused on metric and revenue. You’ll resist distraction and increase your focus, which will in turn lead to greater success.

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