Seeking Wisdom: Five Questions to Ask When Making a Decision

by Ann Sullivan

Why are some people able to make quick decisions while others struggle? One seems to weigh his or her options while the other tends to close his or her eyes and jump. One makes a decision and sleeps like a baby while the other lays awake wondering about the soup that got away.

We expect to toil, at least a little, over the monumental decisions, like who to marry or what business to merge. But what bugs us most is when we find ourselves laboring for an hour over which throw rug to buy.

We’ve all known intelligent people who’ve made really bad decisions that cost them everything. Their lives stand in sharp contrast to the sound judgment written about in Proverbs 3, ironically, written by Solomon himself. “Blessed is the one who finds wisdom,” it says.

This scripture is powerful and begs the question: How does one find wisdom?

These days, it’s not enough to listen to the experts, because if the Internet is any indication, everyone is an expert. And the ability to make bad choices doesn’t seem to discriminate. Race, gender, level of income, or education, identifying red flags seems trickier than ever.

I listened as a young woman blissfully told me about the older man she was about to marry. He’d been married several times before, so I asked, “Why did the marriages fail?” Without missing a beat, she said, “They were the wrong women.” Red flag.

Then there was the dad who asked whether he should keep lending his grown son money. He said he liked helping out in a pinch. And what parent wouldn’t, I thought? Then, he added, “His on-going gambling debts are a little concerning.” Red flag.

Or the woman who told me she was involved with her daughter’s soccer coach. They really connected, she said, and while there was “some” intimacy, it was completely harmless. Red flag.

I think it’s helpful to ask ourselves what ‘need’ is at the core of any decision we’re trying to make. Is it based on emotion? Are we compensating for some unmet need? And how will the decision we make impact those around us?

In his blog called Barking Up the Wrong Tree, Eric Barker mentions some of the more “amusing” bad decisions Americans have made, including those who’ve regretted getting tattooed. According to The American Society for Aesthetic Plastic Surgery, last year alone Americans spent nearly $30 million on tattoo removal.

“Ashley forever!” Not.

Barker actually makes a good point about decision making. He says we don’t need all the information in the world to make the right choice. What we need is the right information, and I agree. I also think I know where the right information can be found.

God has not left us to our own devices, trying to read nature and interpret circumstances, as the deist would claim. He has initiated dialogue and invited us to come to Him where wisdom is found. And why wouldn’t He?

As we look around our world today, genuine wisdom isn’t trendy, and common sense obviously isn’t common enough. But it’s always refreshing to be surprised by what seems obvious–namely, wisdom that has stood the test of time.

When making a decision, these five steps can be extremely helpful:

  1. Define your path. Ask yourself if your choice is in alignment with the core values you’ve developed as a believer. And does it fit into your long-term goals?
  2. Ask someone you trust for advice. Finding a person who has a track record that’s proven wise, reliable, and unbiased will make all the difference. And it’s worth asking, “Where do they get their wisdom?”
  3. Make an honest list of the pros and cons. If you can anticipate an outcome, good or bad, you’ll be much better prepared for it. Remember, difficultly doesn’t mean failure.
  4. Don’t ignore all warning signs and red flags. When your feelings become like that annoying kid in the pool yelling, “Look at me!” every 10 seconds, you may need to take a look. Even if it’s just to shut the kid up.
  5. Never stop asking God for guidance. Life gets cluttered and makes us lose sight of God’s amazing provision of wisdom. He says, “Call to me and I will answer you and tell you great and unsearchable things you do not know” (Jer. 33:3).

When we’ve carefully done these five things, it may be time to confidently take the final step.

So, go ahead, close your eyes and jump.


Ann Sullivan is an author, speaker, and blogger. Download her new free study guide for Permission to Doubt (Kregel). And watch for Ann’s next book on our universal search for contentment. Website: | Blog: