Entrepreneur Confessions: Generalist vs. Specialist

Scott Asai
Apr 4, 2018 · 2 min read

The day I quit my full time job I couldn’t wait to start my own business.

It’s something I always dreamed of post-high school. From a family of five, four of us have been business owners at one time or another (with different degrees of success of course).

The naiveness and arrogance of being young cloaked me as I started; both a blessing and a curse.

On a positive note I thought I could do anything. I wasn’t afraid to pull the trigger because I believed winning was my destiny (boy, was I wrong!)

On the negative side I didn’t know what I didn’t know (it was a lot).

One of my assumptions early on was as an entrepreneur I’d be a specialist focusing on my desired areas only. But what I’ve realized over time is the exact opposite.

When you’re working a corporate job you’re told what to do. But the luxury is not having to worry about when your next paycheck is coming and being consumed with the duties of other departments.

As a business owner, you’re automatically a jack-of-all-trades until you hire people to help you.

This is where the story turns. Although by definition working for someone else makes you a specialist and being your own boss makes you a generalist, the game changer is: delegation.

Chances are if you’re a freelancer or solopreneur, at one time you’ve grown tired of taking orders from someone else. Being the boss is empowering, yet requires much responsibility.

My advice is quickly recognize what your strengths and weaknesses are in context to your business venture and work towards outsourcing challenging tasks ASAP.

According to the StrengthsFinder, you can only be great at a few things. When you spend time trying to improve your weaknesses you dilute your strengths.

Entrepreneurship is hard, but it’s not meant for you to go the journey alone. The reason startups tend to have more than one co-founder is they realize no one can accomplish anything great by themselves.

Even if you are the only one in your company I’m sure you have a support system. It may not be feasible to hire employees, but that’s no excuse to work in a vacuum.

At the start, you have no choice to be all departments, but if you create different job descriptions in your business plan you’ll be more motivated to get to that place than ignore it all together.

Entrepreneurs are meant to be specialists. It just takes careful planning, intention, hustle and time to get there.


Scott Asai is a serial entrepreneur who develops Millennials and helps students with SAT tips. To hear more of his thoughts on educating teens visit his site here.

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