Site icon The Strategic Introvert

Are Strategic Introverts Entrepreneurial Night Owls?

Is it true that strategic thinking introverts are inclined to be night owls?

And if so, is it merely to spend more time in solitude, away from the hustle and bustle of daylight living, or to pursue a lofty business or academic goal?

Many people don’t like working night jobs. Ideally, people prefer to work 9 am-5 pm with weekends off.

Reportedly, night jobs interfere with natural sleep patterns and can be detrimental to your health.

However, journalist Alison Coleman suggested:

The likes of Twitter founder Jack Dorsey, former Yahoo CEO Marissa Mayer, and previous PepsiCo chair and CEO Indra Nooyi have claimed to be able to perform at their best with significantly fewer than the eight hours a night that experts say people need to stay healthy (para. 2).

The task of pursuing business goals or building a body of work entails having the time to develop plans, as well as think about the next steps.

The challenge for strategic thinking introverts is that once they discover what idea or vocation they want to pursue, giving undue energy and attention to an unrelated job is blasphemous.

For these introverts, night jobs are designed to self-fund business initiatives and fuel the engine of creativity.

And being a night owl is within strategic thinking introverts’ DNA because they are often awake anyway, thinking and pursuing ideas.

It is unconscionable for these introverts to give significant time and attention to a job or career they don’t believe in and don’t help create.

After all, discovering one’s high interest often takes years, often referred to as a “calling.”

I worked night jobs for decades to discover ways of building my business and maintaining my brand.

There is a disconnect in many people’s minds when they see you authoring books while wearing a security officer’s uniform.

Night security jobs kept me in the game because they required little of me as I mastered my writing skills.

And based on the data, I was in good company.

Writer Gabrielle Pickard-Whitehead said:

Almost three-quarters (70%) of self-employed and business owners work past their bedtime. Half of the workers in total stay up late, while 1 in 3 is unable to finish work during regular hours (p.1).

Although many strategic thinking introverts may not have formalized businesses, they operate as informal business owners as they move through their developmental stages to achieve their goals.

Although Pickard-Whitehead seemed to refer to business owners working past business hours during the day, the same is true for strategic thinking introverts who use night jobs to pursue their entrepreneurial aspirations.

Establishing a nightly process for growth

I chose night security jobs to build my business because they did not require me to divert my focus away from my entrepreneurial pursuits.

Generally, security jobs require that you make periodic patrols, monitor a company’s video surveillance, and observe, detect, and report any suspicious activities.

I could read and watch YouTube videos about digital marketing, improving my writing skills, and building a profitable business during the night.

And this process did not negatively affect my job responsibilities.

Yes, I was underemployed, and my dating life sometimes suffered, but that was the sacrifice I was willing to make to manifest my ideas.

Imagine how much information you can accumulate studying your craft eight hours a night, five days a week for three years.

The business grew, and I became hooked on the process.

When I left security, I missed my self-described university.

I have since created a shortened version, but it will never be the same.

If you are building a business or exploring an intellectual endeavor, working a night job that doesn’t require much from you is an option. 

Somewhere to go at night

I learned that night jobs gave me a place to go at night for stability. After thirty-five, I no longer went to nightclubs or attended as many social events, so a night job was an excellent place to learn and study as I worked.

One day, I was reading the Wall Street Journal newspaper when I came across an article about a retired corporate executive who at age 85, got up each morning, put on his business suit, and went to an office reserved for him within his old company.

He would get there around 8 am, read newspapers and trade magazines until noon, and then return home.

Instantly, I understood why this routine was essential to his quality of life.

People approaching retirement age often become excited about lying around with nothing to do.

But intellectually driven people look forward to returning to their academically-oriented lifestyle.

Night jobs provide that benefit, and when it’s over, you miss it.

More time for business opportunities

A final benefit, as well as a strategic move, was to have my days available for business opportunities by working nights.

Whether in-person or virtual, I was available to attend meetings scheduled right after work or late afternoon.

Having my days available for business opportunities, I did not have to jump at every chance presented to me.

My night jobs allowed me to form alliances based on mutual benefits as opposed to acts of desperation.

If my business was the hub of my existence, all the related interests for developing it were the spokes.

Becoming a night owl is not only a lifestyle but a strategy for growing a business and improving one’s intellectual prowess.

I was not trying to save the world but merely attempting to solve problems through writing.

To this day, this philosophy has served me well.

I encourage night owls to work nights to create their own world and build a legacy.

Prefacing Robert Frost, I chose the less traveled road; it has made all the difference in the world.

—Frank Carpenter


Coleman, A. (2018, Feb. 22). How entrepreneurs make sleep work for them (and not the other way around). Forbes. Retrieved from:

Whitehead-Pickard, G. (2020, Mar. 4). 70% of business owners and self-employed work past their bedtime. Small Business Trends. Retrieved from:

Exit mobile version