Do You See a Writer or an Entrepreneur in the Mirror?

Woman seeing multiple images of herself reflected

The transition from being a writer to having a full-time writing business is tricky to navigate

Credit: geralt @pixabay 
My mother was an executive in retailing at a time when most women were housewives. My dream was to climb the corporate ladder as far as I could go, and my best friend in college once told me that when all the other little girls were dreaming of having a house and kids, I was dreaming of having a secretary.

She was right.

I worked my way up the ladder of an international financial institution, promotion by promotion, with my goal of having a big office, a big title, a big salary, and yes, a secretary.

I also was a struggling freelance writer because I loved to write, and my dream was to become a full-time writer — down the road.


Someday arrived when I was offered that big job and everything else I had worked hard for; I suddenly faced a surprisingly hard decision.

The offer meant choosing between more prestige, power, and money in a business that thrived on all three, or rolling the dice on whether I could succeed as a freelancer or not.

One choice was a slam-dunk. The other….

There was no turning back. Once I stepped off the corporate ladder, there was no chance of getting back on it.

I made the riskier choice with a mixture of pride and trepidation. I spent three more years building a portfolio of published work before I finally walked away from the bank. I never looked back.

I wish I could say that I started my business with a leap and bound, like Superman. I can’t. My business limped along with stints as a temp to pay the bills.

How You See Yourself Matters

How you see yourself plays an important role in your behavior and actions. If you see yourself as confident and talented, you will act differently than if you see yourself as someone who is diffident and timid. You will take more risks, find greater opportunities, and generally be more successful.

Major transitions shift how we perceive ourselves.

It took about 6 months of mind-numbing temp work and a good chunk of my savings for me to realize why my freelance business was failing

When I looked in a mirror, I saw a corporate executive and a writer, not an entrepreneur and business owner.

I didn’t know who I now was.

Until that changed, nothing would.

“Psychologists assume that identity formation is a matter of “finding oneself” by matching one’s talents and potential with available social roles. Thus, defining oneself within a social world is among one of the most difficult choices a person ever makes.” Shahram Heshmat Ph.D.

What Do You See When You Look in the Mirror?

This new way of looking at yourself is uncomfortable, especially if, like me, you identified yourself by your role before going full-time.

“I am a corporate AVP,” was easy for me to say.

“I am a writer and an entrepreneur,” not so easy.

“You no longer have an “official” title now, except for writer and whatever part-time work you take on. This is one of the most difficult stages. Why? I think it’s that when you have a formal job title, you are an expert in that area, by virtue of your position.” Lauren Kosa

Then there’s the issue of how other people see you.

There are those who think you’re crazy for turning your back on a job with regular paychecks, benefits, and paid time off, and others who support you as you pursue your “little hobby.”

Relatives treat you like the family chauffeur and errand-runner while others support you wholeheartedly. You cling to them like a life jacket in a stormy sea.

You quickly discover that your colleagues have dropped you because you are no longer relevant for their careers. There are no more coffee breaks and long lunches where you carp about management and impossible deadlines.

Even phone calls to catch up soon die away because you no longer have much in common.

You miss the kinetic energy of the workplace. (This is one reason why social isolation is so taxing on those with jobs. We are bereft of energy.)

Writing Must Be a Business to Succeed

It’s easier to head off to a job and put in your 8 or 10 or 12 hours than to sit in your home office and do the same. There are no distractions, no water-cooler chat, no meetings to attend. You should be hammering away, creating, just as you did when you had a full-time job.

Interestingly, what worked for you as a part-time freelancer no longer works when you’re behind your laptop all day.

All day?

That’s right.

You discover that the dream of full-time freelancing is a lot rosier than the reality.


Aspiring writers, newly published writers, and even old-timers sometimes overlook that writing is a business, and writers need to become business people to succeed.

It takes more than being a good writer, however, to make a living at it. We also need skills in:

  • Marketing
  • R&D
  • Sales
  • Copy-writing (different from article or blog writing and more challenging)
  • Finance (taxes, investments, insurance, and so on)
  • Social media
  • Time management
  • Networking
  • And lots more

I started reading and studying entrepreneurship and what was needed to succeed. It took another six months to put in place a foundation for my business.

Office Hours

Every business has office hours — time dedicated to the work.

I broke my office hours into two segments, based on my cycles. I’m a morning person, so I do my creative work then. The afternoon is spent on other activities that support my business.

Use a tool like the Pomodoro technique that lets you work in a series of focused spurts to be more productive. Refuse to be interrupted and hold your boundaries firm. You have a business to run and make profitable.


Amazon may have started selling books, but they didn’t stop there. They have used diversification to take over online shopping.

Let’s be honest: Most of us probably will not hit The New York Times best-seller list — although some of us writing here will and have. But all of us have the opportunity to earn a comfortable living from our business.

Broaden your offerings and explore other areas where you can make money as an entrepreneur.

Writing became just one stream of revenue for me. I added several others, including consulting and teaching workshops and webinars in organizations and online.


Leverage your previous job experience. Whatever your field, you can create and market training programs and other information products unrelated to writing. My first programs were on writing and editing; today, they go way beyond these topics to include a wide variety of professional and personal development skills— all either from my work experience or research.

Explore what interests you and re-purpose that knowledge into revenue streams.


Become comfortable with uncertainty. Freelancing is a volatile business, Editors come and go like the tides, publications rise and fail, payment takes months while you pray the publication stays in business.

Cultivate multiple audiences and areas of expertise.

Don’t just niche your writing, multi-niche and build portfolios for each. If one niche dries up, you have others to fall back on.

You’re an Entrepreneur

That’s what you want to see when you look in the mirror.

“If you want to be an entrepreneur, it’s not a job, it’s a lifestyle. It defines you. Forget about vacations, about going home at 6 pm — last thing at night you’ll send emails, first thing in the morning you’ll read emails, and you’ll wake up in the middle of the night. But it’s hugely rewarding as you’re fulfilling something for yourself.” Niklas Zennstrom, founder Skype

Want more help improving your self-confidence as an entrepreneur? Check out my e-course How to Improve Your Self-Confidence.

Have trouble talking about yourself? See my article How to Tell People Your Good without Bragging.






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