All Articles Leadership Careers Being "Scrappy" and why success lies in how you prepare

Being “Scrappy” and why success lies in how you prepare

"Scrappy" shows us how we might find a realistic path toward achieving more of what we want.

7 min read



We’re all familiar with that form of bad writing that pretends to be expert analysis. It starts with a familiar situation described in broad terms, and the author prescribes an equally broad solution to be achieved through a checklist of arbitrary length.

It’s everyone’s (least) favorite form of business advice — the generic listicle — and yet it works often enough that even thoughtful and/or well-reported journalism and criticism gets headlined this way. Even I have to admit that “10 ways to…” headlines will outperform more nuanced and/or thoughtful headlines.

Why am I getting into the vagaries of clickbait media? Because so much of this advice sends the message that success is a simple process, if only you’d just decide to do it. Or that failure is simply an inevitable part of getting it right. You can come away from these articles with some odd ideas about the roles of failure or grit in life.. 

For a diffierent view, I recently read the book “Scrappy” by Terri Sjodin (Portfolio, August 2016), which shows how hard work is important, but if you think, research and prepare in a more thoughtful and disciplined way, you can find success more quickly and in a more informed manner.

Goals, strategy and tactics

We know that it’s easy to simplify a problem and its solutions. We also know that, in real life, defining the problem is often difficult enough, much less knowing what to do next or how to execute that plan.

On a personal level, taking your situation and improving upon it is difficult, possibly confusing and often frustrating. Sometimes, the answers will be easily discoverable and easily attained, but other times you’ll need to experiment, to take risks. And it all might fail in the end. All of that makes it understandable why we procrastinate, why we fall back onto old habits and comforts.

So, how do you try to change and improve a situation, especially if it’s your career or business? “Scrappy” looks to avoid the pitfalls I mentioned above and stick to basic-yet-commonsense advice about assessing where you are, where you want to be and how you might try to get there.

Most importantly, “Scrappy” doesn’t skip the part many management listicles do: The part of doing the hard work before taking action. Identifying a problem is great, and so is deciding what the desired outcome would be (fixing the problem, overcoming it, developing an opportunity, etc.). And deciding to take action, as Sjodin notes, is an important step. But that is not the same as taking action. Before you can act, you must:

  • Come up with ideas, and determine which ones are best
  • Do your research, including into whomever you need for guidance or that you wish to influence.
  • Determine the timing of your plan.
  • Test it — this includes a “premortem” to examine how and why this plan might fail.
  • Then, take action.

Essentially, goals and strategy matter, but don’t forget that tactics are not the same as strategy. Developing the right tactics, before and after you take action, is how goals are reached and strategies executed.

The ethics of influence

Many listicles do not have space to address any ethical quandaries that may result because of your plans or actions. Now, they usually do not endorse unethical behavior, such as lying to people or being overly aggressive in pursuit of a target. That’s good!

However, such articles usually fail to offer any guidance as to the boundaries of their advice. When does doing X mean you’re a go-getter and when does it mean you are freaking everyone out?

If, as I mentioned earlier, most situations will have particular problems, solutions and available actions, then it might not always be easy to tell what is ethical or a display of smart persistence, versus what is wrong or abrasive or stalkerish.

If you follow the advice in “Scrappy,” you might walk up against this line. The book tells stories of people who bought joke gifts for a potential client, or who confronted an executive at a public conference to ask for a job, or who went to great lengths to get a prospect a round of golf at Augusta, where the Masters is played. These are all aggressive actions, and not for everyone or every situation.

However, what you can learn from “Scrappy,” if you’re a careful reader, is that if you do your preparation, ask good questions, think creatively and know your business, you’ll be able to take such risks with a higher degree of certainty.

And in case you’re inclined to brush off this advice, bear in mind that being too scrappy isn’t beneficial. As Sjodin writes, “You are only going to dig as deep as it’s appropriate within the context of the professional relationship. If you go farther than that, it’s called stalking, and that’s creepy.”

Stop being negative

“Scrappy” does not promise success, and it also doesn’t pretend effort alone gets the job done. And failures will occur. But put all of that aside for the moment. Before any of that can happen, you need to have the right attitude about yourself and what you want to do.

Depending on your personality or how your day has gone, it’s easy to look at a problem and imagine how insurmountable the barriers are, or how many obstacles there are, or how you’ll never figure it out. But, Sjodin writes, what if you did the opposite?

“Expand your vision of what could really happen in your life and ask yourself a few ‘what if?’ questions before opting out. … If you could be, do, or have anything you wanted, what would you choose? Have you tried to get it? If so, what happened? If not, why not?”

Not everything is possible. However, Sjodin urges us to put that aside, to “get out of your own way,” and imagine what good could happen. If there is a failure, OK. That’s part of taking a chance, part of trying to improve yourself, to push yourself past your discomfort into new possibilities.


“Scrappy” covers all of the above and more than I can cover today, but one last section I wanted to mention was Chapter 9, “Leaving Room for Serendipity.” That’s a word that’s often forgotten in a world (and economy) where everything wants to be on-demand and customizable.

Why would we want the element of chance in our lives? For one, many of us know that even well-meaning processes and rules can stifle randomness and discovery. For Sjodin, serendipity is simply acknowledging that little in life can be fully planned and controlled. And, just as we see with scrappy people who push past early setbacks, or how we should coach ourselves to look for opportunities instead of obstacles, the unpredictable nature of serendipity can be a good thing.

The examples Sjodin provides are, of course, stories of happy endings, but there’s an important message in there: “Don’t limit your options with old beliefs and your negative forecasting; you don’t know how the journey will end or how things will unfold.”

We know little of what’s to come, for us or for others. There will always be more to learn than we possibly have time for.

If there’s one thing to take away from “Scrappy,” it’s that while we cannot dictate outcomes, we can control how we react to today’s reality in service of a better tomorrow.


James daSilva is the longtime editor of SmartBrief’s leadership newsletter and original content, as well as newsletters for entrepreneursHR executives and various other industries. Find him at @SBLeaders or email him.