Paradox: Stay the Course or Bail

I’ve posted before on the paradox of planning, meaning that sometimes you need to stick to the plan, and sometimes you need to revise. And leadership, and management, is knowing how to tell which situation is which. There are no formulas for that. Some things are always case by case, no rules.

I’m reminded of this reading Seth Godin saying “when the new stuff doesn’t work, do the new stuff more and better” from the author of The Dip. That seems like a contradiction. In What to do when the new thing doesn’t work, his post today, Seth says:

From the start, you have to choose a path and stick with it. Either you are on the path of the TV Industrial complex, and you’re prepared to promote and spam and spend and make average stuff for average people… or you are busy embracing the new media for everything it can offer.

In The Dip — a great book — is about knowing when to bail. Be the best or get out.

Sometimes we get discouraged and turn to inspirational writing, like stuff from Vince Lombardi: “Quitters never win and winners never quit.” Bad advice. Winners quit all the time. They just quit the right stuff at the right time.

Hmm … seems like a contradiction here, but maybe it’s just the built-in paradox that trips us up. Here’s where he brings it together, to my mind; a one-sentence paragraph near the bottom.

Don’t get stuck in the middle. It’s painful.

One of the hardest things we do, in business, is figuring out which is which. To be sung, I suppose, to the tune of the old folk-country song, the gambler: know when to hold ’em, know when to fold ’em.

* * * * *

Tim Berry, Entrepreneur and Founder of Palo Alto Software, and Borland International About the Author: Tim Berry is president and founder of Palo Alto Software, founder of, and co-founder of Borland International. He is also the author of books and software on business planning including Business Plan Pro and The Plan-as-You-Go Business Plan; and a Stanford MBA. His blog is Planning Startups Stories.




Tim Berry Tim Berry is Founder and Chairman of Palo Alto Software, Founder of Bplans, Co-Founder of Borland International, Stanford MBA, and co-founder of Have Presence. He is the author of several books and thousands of articles on business planning, small business, social media and startup business.

9 Reactions
  1. That is a tough question to answer and I think its a combination of knowledge, experience and a little bit of faith. Thanks for the advice.

  2. Quitting is a tough call to make. I agree that experience is an important factor along with sticking with your gut instinct. There can be a lot said for making a decision based on something that just doesn’t feel right. Sometimes you just know.

  3. I think if you stay the course, keep yourself focused and learn to make decisions that you’ve thought through – thought them through into the future – you’ll be allright. You’ll make good decisions for yourself and your business.

    Like he said, “Don’t get stuck in the middle.” Think things through completely. Don’t just think of the immediate benefit, think through it long term. And once you do that, mull it over for a while and let the answers come to you.

    I think the worst thing anyone can do is make an immediate decision about something that will have a long term impact. Just take a little time and you’ll feel you’ve made the right choice.

  4. Martin Lindeskog

    We got stuck in the middle and it was painful. But we survived and quit certain things. We will continue with the basic idea, but in a new form and and shape. We have learned a lot, established plenty of contacts that are interested in a cooperation in the future. I got inspired by recent tweets and post I have read on co-working, digital nomads and the idea of a “third place” between your home and office.

    I have to get The Dip.

  5. @Martin re The Dip: Yeah, you do. Like every other Seth Godin book I’ve read, short, well written, and thought provoking. Regards, Tim

  6. Excellent content here and a nice writing style too – keep up the great work!

  7. Tim: Thanks again for the book tip.

  8. Does anyone have a good story of an entrepreneur making this decision? Books and sayings are one thing, but I LOVE hearing how individual people have taken these ideas and actually used them in their business. Doesn’t matter what the result was…since we know we all learn from our mistakes. But what does matter is seeing the thought process in action: What specifics about the business environment were important? What part of the decision was analytical and what part was intuitive? What factors about the business were important — e.g., were there other opportunities, was the CEO just plain sick of it, did a specific person leave so it was too difficult to carry out? The devil (and God, to quote Lavoisier) is in the details.

  9. In my experience working with clients of small to mid size companies, I have found that often senior management is ready, willing and able to move in one direction or the other (stay the course or bail) but they have a much harder time deciding when to do so. Some bail too early, others too late; and others stick to the plan way too long. The magic seems to be in understanding the timing.

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