There’s an old legend told about the guy who wanted to borrow an axe from his friend—we’ll call him Yankel—who lived on top of a hill, just on the edge of town.

As he trudged up the hill, our protagonist started thinking, “I just know it. I’m going to ask Yankel for his axe, and he’s going to tell me, ‘But hey, you looked at me the wrong way the other day at the bank!’

“Then I’m going to have to explain to him that it was a hard day and my kid was sick.”

Our friend continues musing, “Yankel will certainly tell me, ‘Yeah, but I don’t know if I can go a whole day without my axe, you sure you really need it?’

“Then, I’m going to have to convince him that I really do need it, and get down on my knees, ugh!”

The entire time our friend drags his sad body up the hill, he’s thinking of the elaborate conversation he’s going to have with Yankel and how difficult it will be. Soon enough, he finds himself at Yankel’s door and gives a loud rap.

Yankel opens up, and before he has a chance to say anything, our friend blurts out in righteous fury, “You know what?! I don’t need you or your axe! Goodbye!” and slams the door in his face.

It’s a funny story about someone making way too many assumptions and then getting heated up about it. But the truth is, we all engage in such foolishness from time to time. Who hasn’t been faced with a task, a challenge, or a job, and then spent needless amounts of time coming up with creative reasons why it’s going to be too hard?

What can we do to escape such defeatist tendencies?

Caleb Stays the Crowd

Our parshah famously relates the debacle with the 12 spies. The freshly minted Israelite nation was on a roll and well on its way to the Promised Land. Alas, they came up with the very bad idea of sending spies ahead to scout the land, and so, 12 men were duly dispatched.

The spies returned with a dastardly report and sent the entire nation into a tailspin. “The people there are huge, they’re fortified to the teeth, and plus, the fruit are super strange!” they cried—and the people lost their minds.

Amid the chaos, the Torah tells us that not all 12 spies were bad, as there were two notable exceptions, Joshua (who eventually assumed Moses’ position after his death) and Caleb. The Torah describes how right in the middle of the hysteria, Caleb jumped in:

“Caleb silenced the people to [hear about] Moses, and he said, ‘We can surely go up and take possession of it, for we can indeed overcome it.’”1

Noting that the reference about Moses is a bit out of place, Rashi explains that Caleb actually employed a classic bait and switch: capitalizing on the people’s anxiety about Moses’ leadership capabilities, he caught their attention by crying out, “Is this the only thing the son of Amram has done to us?” With their undivided attention, he switched gears and exhorted the people: “Didn’t he split the sea for us, bring down the manna for us, and cause the quails to fly down to us?”

It was a deft move, and for a brief moment, it seemed like it may have even worked. Unfortunately, the other spies picked up where they left off, continuing to disparage Moses and … you know the rest of the story—it wasn’t pretty.

But here’s the question: Why did Caleb choose these three specific examples of Moses’ accomplishments? At that point, Moses had a long, impressive résumé, so why did Caleb pick these three incidents to illustrate his point?

Multiple Concerns

A close examination of the people’s fears as recorded in the Torah reveals three specific fears, and it was to these particular fears that Caleb was responding. Take a look:

“However, the people who inhabit the land are mighty, and the cities are extremely huge and fortified, and there we saw even the offspring of the giant. The Amalekites dwell in the south land, while the Hittites, the Jebusites, and the Amorites dwell in the mountainous region. The Canaanites dwell on the coast and alongside the Jordan.”2

Three concerns are listed: (a) The inhabitants of Israel are mighty, (b) again, in Israel, you have Amalek, and (c) various nations pose a challenge along the way.

So, Caleb addressed each concern individually. They are each individually fascinating, but life is short, so we’ll focus on just the last one for now.3

The final concern about the nations along the way is unique. You see, even after the people were placated that G‑d would have their back in the Promised Land—after all, that was the plan!—there was still room for concern: What if unexpected challenges arose along the way to the real showdown? Who’s to say that everything would be fine in such unchartered waters? Maybe they wouldn’t even make it to Israel at all!

Your Inner Creative Defeatist

Let’s stop for a moment and remind ourselves that such concerns are not limited to a bunch of ancient hysterical ex-slaves in a desert. They’re very much part of my and your life, every day.

Think about it: have you never entertained such creative calculations of anxiety?

Say someone is struggling with alcoholism, and they finally decide to tackle this destructive habit and clean up their act once and for all. They’re determined, they’re strong, and they tell themselves, “I can do this!”

And then… Sigh. It happens.

They get anxious and worried. “What if I get some really bad news and I won’t have the courage to withstand the urge to drink? What if my buddies come over and start pressuring me to throw one back? What will I do?”

They get increasingly concerned about all the “what ifs” that will happen along the way, and pretty soon, they’re too paralyzed to even take the first step.

Or say someone is not yet fully Shabbat observant, and they decide they’re going to take the plunge and observe a full 25-hour Shabbat. They clear their schedule, make sure everything is set up at home, and they’re ready to do it!

And then … it happens. The creative inner defeatist, that little “spy,” starts doing its thing. “What if my friends invite me to the movies and I’ll be in a bind if I refuse? What if I’ll be so bored at night, I won’t be able to resist the temptation to check the football score, the after-hours stock market, and my neighbor’s cat pictures on Facebook?”

Pretty soon, the determination is gone—and all because of imagined challenges that may or may not come up along the way.

Caleb’s Response

To this, Caleb responds, “Remember guys: G‑d gave us the manna in the desert.” The entire journey in the desert was pretty much an afterthought. The destination was Israel, not the Sinai Desert, and yet, even along the way, G‑d took care of the people in a most miraculous way.

Caleb’s response is unequivocal: Nothing is too big or too small for G‑d, and if you place your trust in Him, it won’t be for you either. There are challenges in your life that no one else has, and yes, you are uniquely equipped to rise up and meet those challenges. Never be afraid of all the “what if” scenarios that threaten to torpedo your resolve and derail your determination.

Just put your first foot forward and tackle your challenges. Take the first step towards that new resolution you made last time you were inspired by the rabbi’s speech and don’t be concerned about stuff that may happen as you head down the path to victory.

G‑d has your back. G‑d believes in you, and you should too. Don’t worry so much, He’ll take care of you every step of the way.4