Cultivate Enterprise to Take Initiative and Seize Opportunity

We can put ourselves in situations or environments where we are more likely to encounter opportunity. We can teach ourselves to better recognize and evaluate opportunity. If we want to seize and exploit an opportunity, however, we must take initiative. We must act.

A bias toward action, the willingness to do something different or difficult, the eagerness to embrace a bold undertaking – these are the hallmarks of the enterprising person.

Some people are more naturally enterprising than others, to be sure. They are inherently driven, ambitious, self-starting go-getters. Others need to look a little harder to find their motivation.

No matter. Regardless of where we fall on the action orientation continuum, we can cultivate the quality of enterprise. We can develop specific tendencies that will move us to act when action is needed.

Enterprise is often associated with business, entrepreneurship, or other material endeavors. However, we can apply enterprise to a number of pursuits, whether profit is our motive or not.

It is enterprise that compels us to take the first step down a promising path. At some point we have to stop thinking, planning, analyzing, justifying, and rationalizing and move forward.

“Even if you are on the right track,” said Will Rogers, “You’ll get run over if you just sit there.”

Characteristics of enterprising people

A review of the academic literature reveals a set of characteristics common to enterprising people.

Dr. Sally Caird of the UK’s Open University developed a self-assessment tool for measuring some of these tendencies. Her General measure of Enterprising Tendency (GET) instrument assesses people’s tendency to start and manage projects, and is based on the following core characteristics:[1]

  • Need for achievement. Enterprising people are driven, energetic, and motivated. They are optimistic and have a vision for the future. They have a strong task focus and are committed to getting things done. They set challenging but realistic goals, and are persistent in pursuit of their aim.
  • Need for autonomy. Enterprising people are independent and self-expressive. They are individualistic and like to do things their own way. They are often unconventional and opinionated, are sometimes stubborn, and prefer being in charge to taking orders.
  • Creativity. Enterprising people are imaginative, innovative, and inventive. They have a knack for synthesizing ideas and information. They seek novelty and change, and do not like the constraints of set routines. They are intellectually curious, ideologically versatile, and are resourceful problem solvers.
  • Calculated risk-taking. Enterprising people are comfortable making decisions in conditions of uncertainty, and with incomplete information. They are aware of their abilities and limitations, and they are skilled at evaluating the benefits and costs of a given course of action. They actively seek the information and expertise they need to evaluate opportunities.
  • Internal locus of control. Enterprising people believe they can shape their future and make their own luck. They want to achieve success on their terms, and take personal responsibility for overcoming obstacles. They are confident and determined, and they see a strong correlation between effort and results.

A lot of academic research connects enterprise with market-oriented behaviors or the entrepreneurial mindset. However, all people can exhibit enterprise in almost any domain of life.

Business psychologist Marco van Gelderen conducted a random telephone survey asking 462 people if they could provide an example of something enterprising they had done in the past three years, and why they considered that action enterprising. He found that, “people perceive themselves as showing enterprising behavior in different activity realms, and that dimensions of enterprising behavior change according to realm of activity.”[2]

The respondents in van Gelderen’s survey mentioned many of the same characteristics featured in Caird’s assessment tool. But they also included things like being active, organizing things, personal development, perseverance, thinking ahead, helping others, earning money, and doing something unusual.[3]

While there may be some variance among professionals and lay people as to the specific behaviors that indicate enterprise, the broad consensus is that enterprise at a minimum involves being proactive about tackling some project or task.

To that end, there are some simple methods we can all use to increase our tendency toward enterprise.

How to be more enterprising

“It is easy to sit up and take notice. What is difficult is getting up and taking action,” said the great French realist Honore de Balzac, allegedly, somewhere.

Whoever said it, that’s the crux of being more enterprising. It doesn’t matter how many opportunities we see. What matters is how many opportunities we seize. Enterprise requires taking initiative, accepting risk, and acting boldly.

Don’t wait for the perfect time

There is probably no perfect time to start. You will never have the perfect combination of time, money, talent, skill, motivation, and resources. Conditions will always be uncertain, you will always have doubts, and it will never be easy.

Sometimes we just have to plunge in and get going before we feel completely ready. Actually starting something is usually the fastest way to build our skill and confidence anyway.

That doesn’t mean you should act rashly. If your dream is to open a neighborhood ice cream shop, and investing your life savings would still leave you grossly undercapitalized, by all means wait until you’ve secured more funding.

It does mean, however, that at some point we have to stop listening to all our excuses for not starting and start looking at all the reasons why we could start.

What will you have a year from now? A year’s worth of accumulated experience, knowledge, and skill? Or a bigger collection of excuses for not starting?

Whatever you’re doing won’t be perfect

Ah, perfectionism. Dream snuffer. Initiative squasher.

Whatever you do will not likely ever be perfect. By your standards or anyone else’s. There’s a good chance you expect more from yourself than anyone else expects of you anyway.

Instead of trying to be perfect, just commit to doing the best you can with what you have and continuously improving. If you start with something workable, then engage in an iterative cycle of making it better, you’ll end up with a stronger product or service – or version of yourself – than you would if you were hell-bent on making it perfect before launching.

If you start small, you will learn from small failures and small mistakes. If you try to go too big out of the gate, you may be setting yourself up for a giant, spirit-crushing defeat.

You don’t need all the information

Analysis paralysis, decision paralysis, overanalyzing, or overthinking. Whatever you want to call it, we can easily get so lost in the data and metrics we use to support our decisions that we find it difficult to make any decision at all.

The more choices we have available, the more we procrastinate. One study of 401(k) plan participation rates found that increasing the number of funds available decreased the probability that employees would participate at all.

The study revealed that every 10 funds added would drop participation rates 1.5 to 2 percent. When employees had only two funds to choose from, participation peaked at 75 percent. However, when they were offered 59 funds to choose from, employee participation dropped to 60 percent.[4]

If we have a clearly defined goal, it becomes easier to reduce and filter our available choices. We can usually make a good decision with less than complete information. If we wait until we have all the information possible, we may have missed an opportunity altogether.

Find a comfortable balance between risk and potential reward. Sometimes it’s better to make a good decision when we need to instead of the optimal decision when it’s too late to do us any good.

Understand that most decisions are reversible

Most of us don’t need to make life-and-death, all-or-nothing choices in pursuit of our objectives. We can usually back out of a bad decision, or at least cut our losses and change course before too much damage has been done.

You don’t need to agonize over decisions of low consequence. Do a little research, make a well-informed choice, and move on. Recognizing that a decision is low impact greatly reduces analysis paralysis.

Any time we are starting a new project, we are faced with a lot of choices. If we let all of these little decisions overwhelm us, we’ll never move forward. Good or bad, reversible decisions give us data we can use to make better decisions in the future. Learn something and keep going.


Decatastrophizing can help us overcome some of our fears when starting something new, and can also help us see setbacks as opportunities.

Basically, just be careful not to overestimate the probability of something bad happening, or the severity of the consequences if it should happen. You should also never underestimate your own ability to handle negative circumstances.

By analyzing the worst-case scenario, its realistic probability of occurrence, its concrete impact, and how you might respond, you can increase your confidence and your ability to cope with obstacles. This will help prevent unfounded fears – or at least the fear of unlikely events – from derailing your plans before you get started.

There is no ideal skill set

Any new venture – especially if it’s novel – will require a diverse set of skills. That doesn’t mean, though, that it will require a specific set of skills. Maximize the application of your strongest skills, and acquire some new skills along the way.

If you haven’t yet acquired or developed a particular skill you think will be important, you can either learn by doing or seek help.

Being a beginner isn’t a bad thing. Looking at things with a beginner’s mind can facilitate fresher, more flexible thinking and kick-start creativity and innovation.

Learn by doing

Applying newly acquired knowledge to real-world situations is the most effective way to amplify our skill. Trying and failing and trying again provides invaluable experience. We have to learn anyway, so why not make a little progress while we’re doing it?

Does learning by doing increase failure rates? Sure. But if you learn any other way, you are always learning someone else’s methods and strategy. The only way to develop your own unique approach is refine it as you go along.

Whatever the undertaking, grabbing the reins and taking off – even if on a limited scale at first – provides the most engaging, personal, and integrative learning experience you are likely to get.


Do lots of tinkering and lots of testing. Getting used to improvisational approaches to goals or problems helps us prepare for situations where change happens too quickly for us to plan for it.

Improvising is critical to adapt and remain agile. Leverage whatever tools and resources you have available before assuming you don’t have what it takes.

A big benefit of improvising is that you learn to adapt to disappointing results and find ways to turn obstacles into opportunities.

Encourage feedback

Seek feedback about your ideas early and often. Feedback confirms the things you did right and reveals the things you didn’t, and gives you a lot of valuable ideas and potential fresh approaches.

Feedback can also motivate you to get started, or to persist once you have begun. It’s one thing to be enthused about a new venture, but when we hear from peers who share our enthusiasm, it can really bolster our confidence and push us forward.

Before you begin to solicit feedback, though, have a plan for how you will analyze it and use it. Also, learn to separate constructive and destructive criticism, and be prepared to handle either.

Make manageable, measurable progress

Start with small steps. If your goal seems too daunting at first, break it into more easily attainable milestones.

Tackling and completing smaller tasks gets you started and keeps you engaged, gives you a sense of accomplishment and satisfaction, and increases your confidence and motivation. Enterprise is largely about the habit of getting started on projects, and finding ways to manage them through completion.

Starting small allows you to grow at a comfortable pace, make incremental improvements, and recalibrate your approach. Completing smaller tasks allows you to clarify your goal and make progress without sinking too many resources into one thing.

You can start small and still finish big. Start small, start where you are, and don’t be afraid to restart if you have to.

Be enterprising on your own terms

Enterprise is not a precise quality. As Marco van Gelderen’s study indicates, people  have varying interpretations of which behaviors and characteristics are enterprising. A little introspection should reveal why you are having trouble getting started or staying motivated.

Consider some of the typical characteristics of enterprising people, and decide which of those you feel you need to develop or emulate. Review some of the methods presented here, and choose the ones that will help you take initiative.

Enterprise is a core serendipity strategy because we have to initiate action to exploit opportunity. To be truly enterprising, we must be able to muster the courage to act even in the face of doubt and uncertainty.

You may have a naturally high level of enterprise. If not, you can become more enterprising with a little focus and effort. All you have to do is start.


1. Sally Caird, “General measure of Enterprising Tendency test,” accessed May 28, 2021,

2. Marco van Gelderen, “Enterprising Behavior of Ordinary People,” European Journal of Work and Organizational Psychology 9, no. 1 (2000): 87.

3. Ibid, 83.

4. Sheena Sethi-Iyengar, Gur Huberman, and Wei Jiang, “How Much Choice is Too Much? Contributions to 401(k) Retirement Plans,” in Pension Design and Structure, eds. Olivia S. Mitchell and Stephen P. Utkus (Oxford, UK: Oxford University Press, 2004), 88-91.

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