This week, a young client missed a coaching session.

Unfortunately, it wasn’t the first time.

For several weeks, we had been talking about networking, outreach, and the steps required to find a job. Each conversation seemed to produce another reason why progress had stalled. She wasn’t sure who to contact. She didn’t know what to say. She wanted to make sure her message was right. She needed to think about her approach.

I was getting judgmental.

Then I looked at my own behavior.

I have been trying to grow the speaking and training side of my business. I want to work with more midsize companies helping leaders and early-career employees work seamlessly together. I wasn’t doing much better than my client getting started. I was spending a considerable amount of time researching potential organizations, trying to identify the right decision-makers, thinking about outreach strategies, and wondering whether my materials were polished enough.

Different goal. Same pattern.

The experience led me to a question that I suspect many people struggle with:

When does preparation become avoidance?

Preparation is important. I would never suggest that people blindly jump into situations without doing their homework. Preparation reduces risk, builds confidence, and improves outcomes.

The challenge is that preparation can quietly shift from being productive to becoming a very convincing form of procrastination.

Researchers have studied this tendency for years. Psychologist Barry Schwartz’s work on maximizing found that some people devote enormous effort to finding the optimal decision before acting. While that sounds responsible, maximizing is also associated with increased anxiety, delayed decision-making, and lower satisfaction with outcomes. The search for the best choice can become so consuming that no choice gets made.

I see many early-career employees fall into a version of this trap during a job search.

They all ask, “What should I say?” Even after we have scripted the basics of a conversation, they want the perfect answer to every possible question before they reach out.

They also worry that one awkward networking conversation will impede building a relationship. Or that asking a basic question will make them look inexperienced.

The irony is that one of the points of a networking conversation is to build rapport, and that is not going to happen if the conversation is too scripted and forced.

To be honest, the same dynamic is going on in my business development.

As I consider reaching out to organizations about speaking and training opportunities, I find myself thinking, “What if I waste a valuable contact because I don’t say the right thing?”

Beneath all of this planning is often something else: fear.

Not fear of working hard. Fear of getting it wrong.

Psychologists have long observed that people are more motivated to avoid losses than to pursue gains. In practical terms, we tend to focus more on what might go wrong than on what we might learn. So a networking attempt becomes a test of our competence rather than an opportunity to gather information.

The challenge is that fear often shrinks after action, not before it. Confidence is frequently the result of the experience rather than a prerequisite for it. Most of us don’t become confident and then act. We act, survive the experience, and become a bit more confident as a result.

I coach my clients that most people are far more forgiving than we imagine.
One networking message rarely determines the outcome of a career. One outreach email rarely determines the future of a business relationship.

What often creates more damage is waiting months to take action while trying to eliminate every possible uncertainty. This is where another body of research becomes useful.

Entrepreneurship researcher Saras Sarasvathy studied how experienced entrepreneurs make decisions in uncertain environments. One of her key findings was that successful entrepreneurs often start with the resources they already have and learn their way forward. Rather than trying to predict every outcome, they take action, gather information, and adjust. In other words, they allow action to create learning.

Organizational psychologist Karl Weick reached a similar conclusion through his work on sensemaking. His research suggests that successful people frequently act their way into understanding rather than think their way into understanding. Action generates information. Information generates clarity.

There are some problems that cannot be solved in advance. You cannot fully understand how potential clients will respond until you contact them. You cannot fully understand networking or searching for a job until you begin having conversations.

At the same time, I don’t believe the answer is simply to “go for it.” Preparation matters.
The challenge is determining when you have enough information to take a reasonable next step. Once you’ve crossed that threshold, more planning often produces diminishing returns.

This is where the work of behavioral scientist BJ Fogg becomes valuable. Fogg’s research shows that people overestimate the importance of motivation and underestimate the importance of small steps forward. Rather than waiting until they feel ready, successful people reduce the size of the next step until it feels manageable.

For an early-career job seeker, the next step may be identifying one person and sending one message. For me, it may be identifying one business leader or conference organizer and sending one outreach email. Neither action is likely transformative, but both actions create information and a better idea of what to do next.

So, the question I am asking myself right now is the same question I am asking many of the young professionals I coach: have you gathered enough information to take the next step?

If the answer is yes, the next lesson probably isn’t hidden in another article, another webinar, or another week of planning. It’s waiting on the other side of action.

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Resources

Fogg, B. J. (2020). Tiny habits: The small changes that change everything. Houghton Mifflin Harcourt.

Kahneman, D., & Tversky, A. (1979). Prospect theory: An analysis of decision under risk. Econometrica, 47(2), 263-291.

Sarasvathy, S. D. (2008). Effectuation: Elements of entrepreneurial expertise. Edward Elgar Publishing.

Schwartz, B. (2004). The paradox of choice: Why more is less. HarperCollins.

Weick, K. E., Sutcliffe, K. M., & Obstfeld, D. (2005). Organizing and the process of sensemaking. Organization Science, 16(4), 409-421.