Multi-Disciplined: Why the Best Entrepreneurs Wear Many Hats

Photo by Clem Onojeghuo on Unsplash

Entrepreneurship isn’t a singular job. It’s actually better seen (and thought of) as an amalgamation of different jobs. You’ll be responsible for overseeing a number of different departments as your organization grows, and you’ll be taking care of duties ranging from the very big (such as securing venture funding) to the very small (such as paying your office’s water bill).

Generally, the less people you have working for you, the more “hats” you’ll have to wear. For example, if you can’t afford a financial advisor or accountant, it will be on you to keep track of your company’s finances on top of all your other responsibilities.

Some entrepreneurs find this boring or irritating — they got into business to make decisions and come up with broad strategies, not to get involved with other roles and departments outside their range of experience. But the best entrepreneurs are the ones who thrive in this multidisciplinary, demanding, multi-hatted role.

A Marker of Adaptability

First, think about what it takes to try on a “hat” that wasn’t intended for you. Imagine a designer who steps in to help solve an accounting problem, or an account manager who gets a glimpse of an engineer’s daily routine. These represent unfamiliar worlds, and in order to survive in an unfamiliar world, you have to think on your feet. You have to be open to new experiences, humble enough to recognize that you’re out of your element, and quick enough to catch mistakes you may not even realize you’re making. In a sense, transitioning between disciplines gives you practice in adaptability, which as you know is an indispensable quality of entrepreneurs. Things can and will change quickly for your business, so any experience you have in rapidly adapting to new scenarios is going to help.

A Difference in Perspective

One of the biggest responsibilities of any entrepreneur is to make decisions on behalf of the company. These decisions often have heavy consequences, and extend to multiple areas. For example, making a decision to release a new consumer product could put extra pressure on engineering while giving the sales team extra opportunities to make add-on sales and edging out a new competitor who’s threatening your line of business. Jumping into many different roles in your business gives you a more personal perspective for how those roles function. The more perspective you get on your business, the more thoroughly you’ll be able to think about the ramifications of your decisions, and the better decisions you’ll be able to make.

A Willingness for Risk

Entrepreneurship means facing risks, day in and day out. Just starting a business is a risk in itself, but each decision you make and each new strategy you adopt will form new risks you’ll have to overcome. Performing in roles you aren’t familiar with helps acclimate you to this level of risk. You’ll be jumping in with no knowledge, no training, and no experience, yet you’ll be performing similar responsibilities as people with all three. Getting used to this high-pressure, unknown environment will make it easier for you to willingly take calculated risks at a higher level in your organization.

An Appreciation for the Team

Don’t underestimate the human element of your team. Your account managers may serve a vital, gear-like role in your organization, but they’re also people with thoughts, feelings, and complex relationships with others on your team. Performing separate roles will help you understand what it’s like to be that person (at least to a certain degree). For example, when you step in to manage part of the marketing strategy, you might learn some of the pressures marketing faces from other departments, making you more sympathetic and more aware of potential issues that could arise. This aids you in conflict resolution and crisis aversion.

Drawing the Line

Unfortunately, it’s not in your nor the company’s best interest to alternate between jobs for the foreseeable future of your company’s growth. There’s a point where your adopted responsibilities start to interfere with your abilities to lead the company from a higher level. When you reach that point, it’s on you to make a new hire, delegate some of those responsibilities, or define clearer boundaries in what you’re capable and willing to do. Unfortunately, this point is different for everyone, and there’s no way to tell when you’ve hit it other than judging by your gut feelings.

The next time you’re offered the chance to take on some smaller responsibility unrelated to yours, don’t be afraid to take it. It’s a practice in adaptability, risk, perspective, and teamwork, and even if you later choose to delegate that responsibility, your course of time doing it will help you become a better entrepreneur. Try on as many hats as you can, and learn from the experience.

For more content like this, be sure to check out my podcast, The Entrepreneur Cast!



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Jayson DeMers

CEO of EmailAnalytics (, a productivity tool that visualizes team email activity, and measures email response time. Check out the free trial!