You’ve probably been there. You're staring at a cover letter or maybe a performance review, and you want to say someone has "hustle," but that sounds a bit too casual for the setting. So you reach for a "power word." You think of the word enterprising. It sounds smart. It sounds like you’ve got your life together. But then you freeze. Does it sound natural? Or does it sound like you just swallowed a thesaurus?
Honestly, most people trip up because they treat it like a static adjective. They think it just means "hardworking." It doesn't. Not exactly. If you want to use enterprising in a sentence, you have to understand the specific energy it carries. It’s about initiative. It’s about that specific spark where someone sees a gap and decides to fill it before anyone asks them to.
What Does Enterprising Actually Mean?
Before we start throwing it into paragraphs, let’s get the definition straight. According to the Merriam-Webster Dictionary, being enterprising means having or showing initiative and resourcefulness. It’s rooted in the idea of an "enterprise"—a project or undertaking.
If you call your cousin "enterprising" because she started a lemonade stand, you aren't just saying she's a good kid. You're saying she saw thirsty neighbors, realized she had lemons, and organized a business. It’s a word about action.
It’s also an adjective with a bit of a "go-getter" vibe. You wouldn't usually use it to describe someone who is just really good at following instructions. That’s "diligent." Enterprising is for the person who creates the instructions.
The Most Natural Ways to Use Enterprising in a Sentence
Context is everything. You can’t just wedge it in anywhere. Let’s look at a few different vibes where this word actually fits.
Professional and Career Contexts
In a work setting, this word is gold. It’s a "soft skill" word that managers love. If you're writing a recommendation, you might say: "Sarah’s enterprising approach to the stagnant marketing campaign led to a 20% increase in engagement within the first month."
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Notice how it flows? It describes her approach. It tells the reader that Sarah didn't wait for permission to fix what was broken. She just did it.
You could also use it to describe a specific move. "The enterprising young lawyer spent his weekends networking at local tech meetups to build a client base from scratch." This paints a picture of someone who is hungry for success.
Describing Personality and Traits
Sometimes you aren't talking about a job. Sometimes you're just talking about how someone operates in the world.
"My brother has always been enterprising; even as a kid, he was charging the neighborhood kids a nickel to see his 'rare' rock collection."
It works here because it’s slightly playful. It highlights a personality trait that has been there forever. It’s a more sophisticated way of saying someone is "shrewd" or "clever with money."
Describing a Group or Effort
It doesn't always have to be a person. You can describe a collective effort. "The city's enterprising plan to revitalize the downtown area involved tax breaks for local artists and a new pedestrian plaza."
Here, the plan itself is enterprising. It’s bold. It’s a bit risky. It’s trying something new. That’s the heart of the word.
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Common Mistakes to Avoid
People get weird with this word. They try too hard.
One big mistake is using it as a synonym for "busy." If you say, "I had an enterprising morning cleaning my kitchen," you sound like a robot trying to be human. Cleaning your kitchen isn't enterprising unless you turned it into a professional catering hub while you were at it.
Another pitfall? Overusing it. It’s a strong word. It’s like truffle oil—a little goes a long way. If you use it three times in one email, you're going to look like you're trying to sell something.
The Subtle Difference Between Enterprising and Ambitious
This is where the nuance lives. Ambitious is about the goal. Enterprising is about the method.
If I’m ambitious, I want to be the CEO. I have big dreams. If I’m enterprising, I’m the one finding a way to save the company $50,000 by switching vendors, which just happens to make me look like CEO material. One is the "what," and the other is the "how."
Think of it this way:
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- Ambitious: "I want to climb Mount Everest."
- Enterprising: "I’m going to sell custom-designed climbing gear to everyone else who wants to climb Mount Everest."
Real-World Examples from Literature and News
We see this word pop up in high-level journalism quite a bit. The New York Times or The Economist love it.
A journalist might write: "Through enterprising reporting, the team uncovered a trail of digital breadcrumbs leading back to the offshore accounts." In this case, "enterprising" means the reporters didn't just sit at their desks; they dug, they hustled, and they found a way.
In literature, authors use it to establish character quickly. Think of a Dickensian character. Someone "enterprising" in a Dickens novel is usually a street urchin who has found three different ways to stay warm and fed despite having no money. It implies a certain grit.
How to Practice Using It
If you want to get comfortable with this, stop thinking about it as a "vocabulary word." Start thinking about who in your life actually fits the description.
Think about that friend who always finds the best travel deals by calling hotels directly instead of using an app. That’s an enterprising traveler.
Think about the coworker who taught themselves Python over lunch breaks to automate a boring spreadsheet task. That’s an enterprising employee.
Quick Drill
Try to rewrite these boring sentences using our keyword:
- "He was good at finding ways to make money." -> "He was an enterprising teenager who always had a side hustle."
- "The company tried a new, bold strategy." -> "The company’s enterprising new strategy took the competition by surprise."
- "She figured out how to fix the problem herself." -> "With an enterprising spirit, she bypassed the bureaucracy and fixed the issue herself."
Why This Word Matters in 2026
We live in a world that moves fast. Automation is everywhere. AI is everywhere. Being "diligent" is great, but being enterprising is what makes you irreplaceable. It’s the human element of seeing a path where others see a wall.
When you use this word in a sentence, you are signaling that you value that specific kind of creative energy. You're recognizing the "extra mile."
Actionable Steps for Your Writing
If you're ready to start using this word effectively, here is how to handle it:
- Check the stakes. Only use "enterprising" when there is a sense of initiative or "starting something." Don't use it for routine tasks.
- Watch the tone. It’s a formal-leaning word. It’s perfect for LinkedIn, resumes, and news articles. It’s a bit heavy for a casual text to a friend unless you're being ironic.
- Pair it with action. The best sentences using this word usually follow up with a result. If someone is enterprising, what did they achieve?
- Vary your synonyms. If you've already used it, reach for "resourceful," "ingenious," or "pioneering" next time to keep your prose from getting stale.
Start by looking at your current projects. Is there one that required you to be particularly resourceful? Try describing it out loud: "I took an enterprising approach to my home renovation by sourcing reclaimed materials from local teardowns." Once it feels natural in your mouth, it will feel natural on the page. Use it to highlight the moments where you—or others—went beyond the script. That is the true power of the word.
The next time you're writing a bio or a project summary, look for the spot where "hardworking" feels too small. That’s exactly where an enterprising choice of words belongs. It changes the narrative from someone who does work to someone who makes things happen. That’s a distinction worth making every single time.