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    Grow Your Business
    December 9, 2024
    Ryan Wilson headshot sharing advice about making hard decisions as an entrepreneur

    Bold Moves: Why Hard Decisions Drive Success

    Guest blogger

     | 

    Entrepreneur

    By:
    Ryan Wilson

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    Entrepreneurship is full of decisions—big, small, and everything in between. If I’ve learned anything over the years, it’s that at the end of the day, only a few critical decisions truly define the trajectory of your business. These are the decisions that carry weight—the ones that keep you up at night. In short, the hard decisions. The ones we often delay because we’re waiting for the perfect sign or set of circumstances. Yet, as entrepreneurs, we often know in our gut what needs to be done but somehow struggle to do it. I’ve found that success often hinges on making the hard decisions. No cliché here—mastering the art of making tough choices is the true key to business success.


    📌 My grandmother used to say, "You stare long, you stare wrong." This advice has stuck with me because, in business, hesitation can be costly. We don’t always have the luxury of endless deliberation, and even if we do, we shouldn’t take it. While it’s natural to second-guess yourself, the real skill you need to develop is trusting your gut, assessing the information you have, and taking action. Waiting too long can paralyze progress, and the opportunity you were pondering might pass you by.

    📌 There’s no doubt that making a hard decision is, by definition, difficult. Whether it’s deciding to pivot your business strategy, parting ways with a vendor or partner, or committing to a significant investment, these decisions are rarely black and white. But remember this: the need to make a decision is rooted in something real. That doubt or discomfort you feel? It’s often an indication that change is necessary. Ignoring it won’t make the problem go away—it only delays the inevitable.

    📌 One of the biggest misconceptions I see is that people overestimate the downside of making the wrong choice. Yes, there are risks, but the cost of inaction is often greater than the cost of a misstep. As entrepreneurs our job is to look for the upside. It’s not about being reckless but about recognizing that progress comes from action. You can always adjust and refine as you go. What separates good entrepreneurs from great ones is their ability to act decisively and move forward, even in uncertainty.

    ⚠️ Now, let me be clear: making hard decisions doesn’t mean abandoning your values or forgetting your “why.” On the contrary, your values should be your compass. They anchor you in who you are and why you started in the first place. Lean on them to guide you as you make the cut. Your decisions should reflect the mission and integrity that define you as a leader.

    💡✍ Making tough calls is never easy, but it’s part of the job. And the more you practice this muscle, the stronger it becomes. The path to success isn’t paved with perfect decisions—it’s marked by bold ones. So, the next time you face a crossroads, remember: trust yourself, make the decision, and keep moving forward with purpose.


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    © 2025 Hiscox Inc. All rights reserved. Underwritten by Hiscox Insurance Company Inc., 30 N. LaSalle St., Suite 1760, Chicago, IL 60602. As of December 31, 2024, HICI had admitted assets of $1,985,481,103 and policyholders surplus of $558,441,204. Total liabilities were $1,427,039,899 (inclusive of $846,124,559 of loss reserves) and paid-up capital stock was $4,242,000.

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