The Rewards of Balancing Risk and Opportunity

by | Jul 13, 2015

Editor’s Note: The monthly Ebook Cover Design Awards will appear here next Monday, July 20th, and on approximately the same date in coming months.

As you probably know, I go to a lot of publishing events and I really enjoy doing that. There’s an excitement and energy that seems to invigorate everyone, and together we form a temporary community where we all speak the same language and have roughly the same goals.

Probably my favorite is Mike Larsen’s San Francisco Writers Conference. It sells out every year, and people come in from all over the country to attend.

A lot of these writers have never been to the conference before, so there’s a certain amount of risk involved in going, right?

You’re going to have to pay the fee for the conference, make time to plan and book your flight and hotel for the trip, and the whole thing is going to cost you money and time.

That’s what you’re risking.

Naturally, these writers are willing to take the risk because they see a genuine opportunity as the pay off.

Maybe it’s attending the keynotes, panel discussions, and workshops. There’s always a lot of education packed into the schedule.

For others it’s the chance to meet face to face with an agent or an editor. That’s a big enough opportunity to make you say, “yes, I’ll take the risk.”

But this balance of risk and opportunity is playing out all the time.

Risk in the Pre-POD Days

When I first started publishing my own books, back in the days before print on demand and ebooks, the risk amounted to thousands of dollars in up front payments to vendors and printers, and several months worth of work.

The risk was more than financial, because my name would be on the book. The subject was one no publisher was interested in. What if people who knew me started to think I was a nutcase?

But the opportunity looked big to me too, so I was willing to take the risk. In the end, and I’ve talked about this before, it really was worth the risk. Over the following years I ended up with my own publishing company, started doing a lot of public speaking, and began a lifelong career in independent publishing.

It could have just as easily gone the other way. That’s what makes it a risk.

Stepping Out as a Blogger

There was another moment like that when I started blogging, when I had my very first post ready, but I hadn’t pushed the “Publish” button yet.

What if people hated it? What if someone came along and poked holes in my writing and laughed at me?

In the end I did find the courage to click that button and accept the risk, because the potential rewards were just too great to ignore.

It’s no different when you step outside your own comfort zone to do something that might seem radical. This has been especially true for me in getting help learning the skills I felt I needed to succeed in my writing and business.

—Going to a writing class and sitting and writing in real time, then reading what I had written to everyone else? Terrifying, tons of risk there.

—Paying $260 to consult with an expert in online book sales? Sounds crazy, who needs to do that?

—Spending hundreds of dollars on a course on blogging taught by a fellow less than half my age? Sounds risky to me!

—Spending over $4,000 in one year on advanced instruction in developing online training programs? Are you kidding? “I must be crazy!”

In each case I doubted myself, I resisted, I had internal arguments for hours or days.

But here’s the thing: every time I said “yes” to these opportunities, the rewards I got from making the leap always crushed the risk I had taken.

Every time.

Results Are What Matter, In the End

That writing workshop opened up my writing ability, blocked for over 20 years.

My consult showed me a clear way forward and the exact next steps I needed to take to get my business off the ground.

That blog training? Yeah, I think that’s worked out pretty well.

And the $4,000 in instruction—that was a lot of money to spend, I agree—showed me how to build my Self-Publishing Roadmap course, which has helped many authors and generated many, many more times the revenue than I put into it.

Probably the place I see this most clearly is when I’m consulting with authors. One on one consulting is expensive, because you’re getting not only time and expertise, but experience gained helping hundreds of authors reach their publishing goals.

Now it’s up to each of us to do this risk/opportunity calculation for ourselves. I can’t tell you what to risk and what to keep safe, and I can’t fully estimate what opportunities you might find if you take those risks.

We all have to make sure we’re safe and secure first, and only risk what we can afford to lose. That just makes sense.

But if you think about this risk/opportunity balance, the next time something comes along that both terrifies and excites you at the same time, focus on the opportunity half of the equation. Be daring. Take the leap!


tbd advanced publishing starter kit


  1. Sharon Goldinger


    Terrific post. You’ve taken an amorphous topic and crystallized the essence of it in a way that everyone can understand and relate to. I found it very motivating. Well done.

    • Joel Friedlander

      Thanks, Sharon, I take that as high praise coming from you!

  2. Frances Caballo

    Love this post, Joel. By explaining all the risks you took, you help everyone else to be less afraid to make a similar type of monetary investment in our online marketing careers and book marketing efforts. Thank you!

    • Joel Friedlander

      It’s something I’ve been thinking a lot about lately, Frances, so it’s great to hear your feedback.

  3. Carol

    Great article Joel. Reminds me how many times I was reluctant to spend money for conferences and workshops–and eventually my MFA–feeling I was indulging an increasingly expensive habit. To become the best writer I can be, I have to takes risks, including investing in myself and my writing.
    Thanks for that reminder.

    • Joel Friedlander

      Carol, I’m guessing that the money and time you’ve spent to become a better writer is going to come back to you in results, exactly in the area that’s most important to you.

  4. Ernie Zelinski

    A great article. I agree with you totally.

    Just a note that you and I may have better ability to assess the risk/reward equation than a lot of people. Or in my case, I may just be crazier than most people. Let’s go back to 1989 when I wrote my first book. It was a book on creativity called “The Art of Seeing Double or Better in Business.” Even though I had a literary agent to represent me, no publisher was willing to take a risk on the book. Based on the comments that the agent forwarded to me, it appeared that most publishers thought that the manuscript was written by a ditchdigger whose last three years of education were spent trying to get through grade nine.

    Given that I wanted to prove that all the publishers who looked at the manuscript were a bunch of morons who should be in another line of business, I did not have too difficult of a time convincing myself to self-publish the book. The initial 2,000 copies of the book cost $7,500 to have printed. Because I was having one of those weird out-of-money experiences, as I had been for many years, I had to borrow half of the money from my mother. She later told me she thought that I would lose my shirt and not be able to pay her back ever. Regardless of my mother’s lack of confidence in my entrepreneurial abilities, I figured that I was in a privileged position because I had a chance to prove the moronic publishers wrong.

    Within a year, I managed to sell enough copies of “The Art of Seeing Double or Better in Business” to pay my mother back and justify another print run. I also managed to book around $15,000 in creativity seminars because of the book. Things really improved from then on. In the fall of 1991, I published “The Joy of Not Working”, which has now sold over 280,000 copies, has earned me around $750,000 in pretax profits, and still earns me around $25,000 a year.

    Even with the success that I had with several books, I almost did not publish “How to Retire Happy, Wild, and Free.” It was turned down by 35 American and British publishers in 2003, including Ten Speed Press, which has published “The Joy of Not working” in the U.S. since 1997. In the end I did a profit analysis and concluded that I should at least break even. Good thing, given that “How to Retire Happy, Wild, and Free” has now sold over 250,000 copies.

    This recent comment by one of my favorite marketing gurus really resonates with me:

    “When you do work that matters, the crowd will call you a fool.
    If you do something remarkable, something new and something important, not everyone will understand it (at first).
    Your work is for someone, not everyone. Unless you’re surrounded
    only by someones, you will almost certainly encounter everyone.
    And when you do, they will jeer.
    That’s how you’ll know you might be onto something.”
    — Seth Godin

    And here is a bit of great advice from someone who lived a bit before our time:

    “In the arena of human life the honors and rewards fall
    to those who show their good qualities in action.”
    — Aristotle

    • Joel Friedlander

      Fantastic story, Ernie, thanks for that. What we likely have in common is the understanding that it’s okay to fail when you take a risk, that’s what risk is all about. But I’ve never had a failure (and I’ve had many) where I didn’t learn something absolutely critical. Besides, taking action always comes with risks, so if we want to get anything done, we have to learn to deal with risk in a practical way.



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