How to Be a Financially Impoverished High-Achieving Writer

I’ve promised complete candor with my Medium articles in an effort to help other writers. These are 10 steps NOT to follow from my path …

Everyone thinks I’m wealthy.

More pointedly, everyone thought I was wealthy when I didn’t yet have a proverbial pot to piss in.

To then, I had written several books and movies, been published in a literary journal or two, and have sold television shows of my creation to networks and streamers.

Though today may be a different story, the fact was in the midst of the above I was still struggling — boy, was I struggling — with bills.

I could not make ends meet.

I’m a homeowner and not asking for pity, but the more toys we accumulate, the greater the financial responsibility. And, sometimes, the greater the responsibility, the larger the deficit.

That’s exactly what happened to me. Learn from my mistakes, so you can focus on your writing career as you build to larger obligations.

My Mistakes:

Do not quit your day job until you are ready, meaning a) if you are entrepreneurial, you must have financial reserves to move forward, b) your writing is now earning income that supersedes your day job, and c) you have not only a realistic five-year plan, but an exit strategy should your writing efforts not pan out as expected. My mistake: I followed none of this advice, which was given to me by highly-experienced, entrepreneurial friends. I thought I knew better, and my writing would quickly pay for itself many times over. It did later on, but the stress of many years of hunger (which is not itself a bad thing if you use it to write for your life) nonetheless caused periods of stress that were nearly untenable.

Never sign on a financier or financiers to invest in your work until you are ready. Legal repercussions of structuring a proper entity to hold the money, as well as maintaining fiduciary responsibilities to your investor(s), have driven many writers into bankrutpcy. My mistake: I’ve shuttered a business as I was not ready for those responsibilities. That business had over a dozen financial partners.

If you are part of a couple (or more), understand that said financial burdens will absolutely impact the strength and longevity of your relationship(s). My mistake: I was called a “failure,” and worse, by some who used to trust me. That was another difficult reality to swallow.

Always use an attorney to review your writing contracts. My mistake: I was bit twice there, and frivolously sued. I won, then won again on appeal, though the extreme duress of getting to that point was harmful to not only my reputation at the time (over 15 years ago), but also my health. My blood pressure skyrocketed, and I had to be medically treated on more than one occasion.

Understand that no one is closer to your work than you are. Though you may indeed be a fine, under-appreciated writer, it does not mean the rest of the world will come your way if only you undertake a foolish risk. My mistake: I’ve taken plenty of risks and, in fairness, many have paid off. I still take risks, but along the way I’ve learned the difference between a risk that is calculated, and a risk that is stupid.

You must at all times work on your craft. Content is king. My mistake: I never considered this. For many years, I cockily assumed I was already where I needed to be. I believed, sincerely, that my writing was as good as it was going to get. I learned the hard way, with my first large stack of none-too-kind rejections.

Make the power of the pivot a primary weapon in your arsenal. My mistake: I was too proud to pivot. I honestly believe, today, the old adage: Where there’s a will, there’s a way. There is always a way. But if you continue to move forward with what does not work, you will only attain the same results. This statement is representative of another great chestnut: Repeating the same strategy and expecting a different result is the definition of ‘insanity.’

Never stop writing. My mistake: I became disgusted with my lack of progress at times, and gave up … only to return because I am a born writer. If I did not ultimately continue on as I did, I would not be where I am now.

Never make grand proclamations to friends and family that you are quitting writing. My mistake: I’ve done it, and though friends and family were happy I retuned to the craft, they were also not surprised. Credibility is lost if you do not keep to those promises.

My greatest mistake: I did not realize until my mid-40s (I’m 55 now) that writing is an ongoing process. Writing is a continual process of refining one’s craft, not giving up (but becoming smart as a more productive option), and learning the business of writing. I’ve been periodically guilty of ignorning all of these points.

Please learn from my candor.

This piece, however, is not all doom and gloom. As time went on, the scales tilted in my favor, as they will with you if you don’t give up. Several of my projects have done very well or are doing very well presently. I have a good reputation and I’m proud of my track record.

My writer’s journey has enabled me to honestly share my successes and failures with the world. I was once a school teacher; today I speak around the country at writers conferences, film festivals, and numerous other gatherings on the art and craft of writing.

My takeaway is this has all been part of my journey. Learning from your failures is imperative. Never giving up is equally important.

You can absolutely do this. Find your way, commit, move forward … and again, learn from the mistakes of others.

Thank you, as ever, for reading.

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