You’re feeling drawn towards doing more of the Jewish thing. Maybe you’ve started eating kosher. Or keeping Shabbat. Or perhaps you’ve made a commitment to light Shabbat candles each week. Or it’s just that you’ve started learning and growing in a Jewish-thing way.

But as soon as you put one foot forward on your journey, you feel like you just walked into a mega shopping mall with a thousand shops beckoning and no one there to take your hand.

So here’s that hand. Here’s a few tips to find your way through the shops and aisles and come out with the right gear for you—as well as a pathway for continued growth.

1. Pace Yourself

Like they say, easy come, easy go. Or as G‑d told the Israelites before they entered the Promised Land, “It needs to go step by step. Otherwise, the wild beasts of the field will take over.”1

What are the steps? Depends on the person. Some people need a little nudging along. Others need some gentle, slow-down pacing.

It also depends on the terrain—meaning, what’s going on in your life. As with any terrain, you’ve got to ensure the front foot is firmly on the ground before you put the other one forward.

Some people’s default modality is to jump into the lake to learn how to swim. Most of us need time to first get our feet wet.

Take, for example, the couple that decided one day to keep kosher. They threw out all their dishes and bought two sets of new ones, the rabbi spent a whole day making the kitchen kosher, and they started buying only kosher-certified foods.

Within one week, nobody could remember which spoons were supposed to be for milk and which for meat, the pizza cutter had somehow snuck its way into the dishwasher with the plates from meatballs and spaghetti, and guests had to explain after taking a few bites that no, not all fish are kosher, certainly not ones with whiskers. Their kitchen, the rabbi had to explain, was no longer kosher.

So they gave up.

What should they have done? They could have started with a little internship in the home of the rebbetzin and rabbi. Then they could start getting used to buying kosher products and separating milk and meat. Next, they could get used to two sets of dishes, while reading everything on about keeping kosher.

And then, after a few months, it would be time to make the kitchen totally kosher. For life.

2. Know When to Leap

Yes, there are times for leaping forward. As with any upward hike, there’s going to be occasions where the only way to get ahead is by springing over a stream or climbing over that big rock.

If you’re going to keep Shabbat, at some point you have to say bye-bye to your electronic devices for 25 hours every week.

If you want your children to pass along your good new choices about living Jewishly to their children, you’re going to have to make the leap of putting them in a Jewish school.

Then there’s leaps that demand deep, inner strength, such as breaking up an intimate relationship with a non-Jewish partner.

And then, you stand there at your new vista point, take in the view, take in the air, take a bite of your kosher sandwich and, only when you’re comfortable up there, take the next steps forward. Step by step.

3. Know You Are There Already

But hold on. If you’re moving ahead step by step, aren’t you sinning in the meantime?

No, and the sages of the Torah have a lot to say about this:

G‑d isn’t a tyrant with His creatures.”2

“G‑d only expects from you whatever you’re capable of.”

“The Torah wasn’t given to angels.”3

Get that? G‑d prefers imperfect humans who try hard over sublime angels who sing nice songs all day.

There’s an important principle in halachah: As long as you’re sincerely climbing upwards, rung by rung, you’re at the top of wherever you have to be. Here’s an example:

On Passover, a Jew is not allowed to possess leavened bread. Let’s say you discover some bread in your home during the holiday. You need to destroy it immediately. But that takes time.

During that time that it takes you to find a way to destroy this bread are you sinning by owning this bread?

The answer is no. As long as you are actively engaged in the process of getting rid of this bread that you’ve found, it’s as though you’ve already destroyed it.4

The same with your efforts to fulfill all the mitzvahs and not break any prohibitions of the Torah. Nobody can be expected to suddenly get everything right from the get-go. It takes time to get up the speed to clear the runway. As long as you are fully engaged in reaching that goal, for the moment now, you’re exactly where you’re supposed to be.


For more on this topic, read What Is a Baal Teshuva.

4. What If I’m Not Sure I Believe In G‑d?

You’re on a long road. Doubts come and go like signposts on the highway. There are bumps, there are hills, there are sharp turns. Just keep driving with your eyes on the road ahead and your heart on your goal.

Judaism is more about a healthy way of life than a steady state of mind. That’s a good thing because minds are always in flux, but a healthy lifestyle is built of consistent, healthy habits.

Learn lots of Torah, do lots of mitzvahs, and your belief in G‑d will grow like a well-tended fruit tree.

Read the full article on this here.

5. Always Be a Mentsch

Rebbi said, “What is the straight path (in Torah and mitzvahs) that you should take? A path that fits you beautifully and is beautiful to others, as well.”

So if the path you’re taking is leading you away from the people who care about you the most, it’s time to check whether you’re taking it in the right direction.

After all, Torah is not just between you and G‑d. It’s also about you and others. Torah is supposed to make you a better child to your parents, a better parent to your children, a better spouse, and a better person all around to everybody.

That doesn’t necessarily imply compromise. Rather, think of it as a kind of art form. A halachic life is life as art.

For more on that, read How to Keep Halacha and Keep Your Friends Too.

6. Find a Guide

We call that a mashpia. Or a mentor. Vital, if you’re aiming for sustainable growth.

Many people in your situation have a family that sort of adopts them. That’s really neat. But if you can’t score such a treasure, just target someone you respect and proactively make this person your mashpia.

Another person you’ll need—and it may be the same person—is a rav. That’s the person you ask shaylas. A shayla is like when you don’t know whether something is permissible or forbidden, mandatory or just a good idea.

A mashpia is someone you ask when you know something’s technically permissible, but you don’t know if it’s intelligent or totally nuts.

Like: Am I ready to make my kitchen kosher?

Or: How much of this prayer book should I be saying?

Should I be staying home at night to put the kids to bed with my wife or should I go study Talmud with my rabbi?

One of us wants to be super strict about Passover, and the other one wants to just keep the basics. What do we do?

Should I be getting up in the middle of the night to sit on the floor with ashes on my head and weep over the destruction of the Temple in Jerusalem? Why not?

Sure, you can just wing it, deciding for yourself which way to go. You could also attempt making your way through the Australian outback without a guide or a GPS. It’s just not a smart thing to do.

I don’t have stats, but anecdotal experience tells me that people who have a good mashpia have greater success, more happiness, way better marriages, and far more spiritual growth than the lone cowboys. More sanity, too.

It’s a strange world out there. Don’t go it alone.

Read: Why Do I Need a Spiritual Mentor?

Also: The Difference Between a Rabbi and a Rav

7. Pray at Your Own Pace

Keeping up with the minyan is nice. But priority goes to kavana. That means meaning what you say, and you can’t always mean what you say if you’re rushed to flip pages.

Better, at least at the beginning, to start with the minyan and pray at your own pace.

It’s going to take a year or so. But then, it will flow, it will be natural, it will feel right, it will become important and meaningful in your life. None of that is going to happen if you try to rush the process.

People who attempt to rush the process end up ten years down the road skipping half the words and muffing up the rest with no clue what they are saying, and not much incentive to continue.

People who do it right find that their davening time each day becomes a crucial daily reconnect and core-system recharge. I mean, who wouldn’t want a daily appointment with the Master of the Universe?

8. What Prayers Should I Say Each Day?

Art by Rivka Korf Studio
Art by Rivka Korf Studio

Right now, you need to get the basics. You need to understand what you are saying, why you are saying it, and what are the main things to say.

The basics are to learn:

1. Morning blessings

2. Shema Yisrael

3. The Amidah

Try starting in English and slowly moving that over to Hebrew as you figure out the meaning of the words. If Hebrew is just too hard for you right now, don’t sweat it. G‑d understands any language, as long as it’s spoken by the heart.

Just focus on three things:

1. Pronouncing the words right.

2. Knowing what they mean to the best of your current ability.

3. Knowing that when you say them, you’re in a personal, intimate appointment with the Creator of the Universe who believes in you.

Every month or so, you can add on a little more. If unsure, ask you mashpia for guidance. Eventually, you’ll find yourself figuring out what you’re supposed to say on what verbal cue along with the crowd. One day, you may even discover you can daven together with the minyan—if you find an unhurried, easy-paced one.

Read: Must I Pray in Hebrew?

9. How to Keep Burning

They call you the meshuganeh baal teshuvah. It’s a term of affection that means they think you’re nuts. Because everybody else is walking through this in their sleep and you’re on fire.

That’s fantastic. Don’t try to be like them. Don’t let the flames go out. That’s why G‑d made a high-risk investment with your soul, sending you on your long, circuitous road to mitzvahs, so you would do them with a fire.5 Behave like everyone else and you just blew G‑d’s investment.

Ever see someone dancing to the music he hears through his headset? Looks meshugah, doesn’t he? But that’s only because you don’t hear what he hears.

Taking the long road makes sure you hear the music.

So, are you meshugah? A little bit, maybe. But then, the prophets were also called meshugah.6

As you learn more about what you’re doing, learn a lot of Torah, and learn to love these people for who they are, your mitzvahs will become better integrated into your life until they’re seamless. You’ll have both feet firmly planted on the ground.

But you need to always keep burning. Don’t waste G‑d’s investment.

10. Never Stop Learning

Art by Rivka Korf Studio
Art by Rivka Korf Studio

If you’re a Jew, your major occupation in life is learning Torah. “When you sit in your house, when you walk on the street, when you lie down at night and when you wake up in the morning”7 your head is into the Torah you are learning.

Imagine trying to move upward while standing on the down-escalator. The only way to keep going up and not down is by learning more and more Torah every day.

If you didn’t grow up with this, then multiply everything I just said by one order of magnitude, at least. Don’t be stuck with a post-graduate secular education and a Sunday school perspective of Torah.

Learning Torah doesn’t mean simply gaining knowledge. That’s important, but there’s something far more important.

What do you talk about at the dinner table? What do you listen to when you’re driving to work? What do you think about before you go to sleep at night? What do you pick up to read when you get up in the morning?

Learning Torah is about where you stick your head. Because if it’s not immersed in Torah, it’s going to find all sorts of crazy stuff to immerse in, and it gets real hard to get it out of that gooey stuff.

11. What should I learn?

Priority goes to knowing what’s right and what’s wrong, what you need to do, and what you need to avoid.8

Priority also goes to whatever inspires you best. No point in knowing what you have to do if you’re not inspired to do it.

For the dos and don’ts, there’s Kitzur Shulchan Aruch and other more recent works on basic halachah. There’s a lot of good material on this site, as well. You’re going to have a lot of questions, and if you’re not driving some rabbi or mashpia nuts with them, it’s likely you’ve got it all wrong.

For inspiration, read lots of stories of tzadikim, get your head into chassidut and whatever else in Torah inspires, and attend the classes of someone who inspires you.

Don’t rely on classes alone, though. It’s too easy to sit back and let the waves glide over you without really taking a thing in. Find someone to study with you one-on-one. If there’s no one local, check out JNet. They’ll set up a personalized partner for you at no cost.

The best investment you can make is to take a few months to study in a yeshiva. The immersive experience pays off many times over. But if you can’t, make your own yeshiva at home. Talk with your mashpia and build a program for yourself.

The only way any of this is going to happen is if you have set times for studying these things. All real change only happens through habit.

But let me warn you: As soon as you fix those times for learning Torah and attending classes, the entire world is going to come down on you like a flood to wash those fixed times away. Guaranteed.

Stand firm. Don’t budge. It pays off. We weren’t called a stiff-necked people for nothing. Indeed, it’s the only way we’ve survived.

12. Ask Hard Questions. Be Patient With the Answers.

“The timid never learn,” says the Mishnah.9

Rabbi Shlomo ibn Gabirol (Spain, 11th century) put it more forcefully: “Ask stupid questions. The best of all human qualities is the willingness to ask.”10

Of course, chutzpah is generally not a good thing, as the Mishnah says, “The brazen-faced end up in hell.”11 But when it comes to learning Torah, it’s just the opposite. In the game of gaining wisdom, it’s the die-hard nudniks that win.

Here’s a personal note:

In my initial interactions with Torah teachings, I had hundreds of questions. Some were fairly trivial, but many were highly critical. Even some that seemed to pull out the carpet from under the entire structure of Judaism.

Today, instead of hundreds of amateur questions, I have thousands of better-educated ones.

Did I get answers along the way? Yes, many very good answers. A lot of lousy ones, too. The good answers generally took years to find, sometimes decades. Some just walked in the door this year. The lousy answers came as soon as I asked.

What most surprised me, although it shouldn’t have, is that nothing I ever asked was original. It turns out there was always someone, somewhere along the long road of Jewish history, who had asked the same thing. Often in very different words. Often from a very different perspective. But the answers they found, if they did, led to a place of a higher understanding.

Even if they never found an answer, it’s comforting to know that you’re part of a people that believe it’s healthy to ask. Indeed, it’s a requirement. It’s called “learning Torah.” Learning Torah means it has to make sense to you. Not to your teacher, not to the rabbis in the book, but to you.

“If anyone tells you they tried to figure out the answer, but did not succeed, don’t believe them. If they say they say they didn’t try, and they got the answer right away, also don’t believe them. Only if they say they worked hard and they got an answer, then you can believe them.”12

And until you get an answer? Keep learning, keep doing, with a whole heart and a lot of faith. Jewish life still works, and it’s been working amazingly for three and a half thousand years. The bush keeps burning, but it doesn’t burn away.

We all have a problem living with cognitive dissonance. If there’s a question burning, we run for the closest bucket of whatever to put it out. Maturity is knowing that it’s okay to let it burn for a while. Even for a lifetime. It won’t destroy you. That’s the only way to get quality answers.

In fact, if you get close up to that burning question and stand there long enough, you might even hear G‑d calling you from within the flames.

A Few More Tips

The Fold-up Kitchen

You just started keeping kosher this summer and now your dorm-mate is frying bacon every morning. In return for your highly sensitive and accommodating explanation of your kosher pots and pans with the red and blue stickers you pull a blank stare. This is, after all, her kitchen as much as it is yours.

Do not despair, others have tread these waters before you and survived. How did they do it?

They discovered you can cook almost anything on one little device called a countertop Pizza Maker (best known as a “Betty Crocker,” just because they made the first one). Scrambled eggs, chicken cutlets, knishes, chop suey, steaks. Even pizzas.

(Okay, for pizzas you’ll need a second Betty Crocker.)

So no need to make a kitchen kosher only to have it de-kosherized within a day. Here’s your entire kitchen, and it fits neatly in a drawer with room for a few cooking utensils. All you need now is one little lock.

How to Get Out of a Handshake:

I know what it’s like. You have all these friends of the opposite gender who are used to receiving a warm hug each time they see you and now you won’t even touch their extended hand. In business, it’s particularly precarious.

Yes, there are some halachic authorities who will permit businesslike handshakes. But, having run my own business for several years, I can tell you that not every business handshake is just business. It’s better to be as consistent as possible, especially with those you do business with frequently.

One observant executive told me how he always manages to be holding a coffee in one hand and a Danish in the other when one of these situations is about to arise. (Actually, the full cup of hot coffee alone is enough to ward off any sort of physical contact if you look clumsy enough.)

But if you can’t do that, the best policy is to have a cogent, reasonable explanation for your newfound behavior, one that fits your personality and sounds natural. And always with a friendly, confident smile.

The truth is, limiting who you can touch and when is probably the most liberating and empowering feature of the halachic lifestyle. Touch has a deep impact on our subliminal psyches, our sense of self-dignity, and our emotional attachments, much deeper than we recognize.

Besides, placing boundaries can save you from many awkward social situations. Every living thing preserves its integrity by having a membrane to define it. So does every country. People, too, need borders.

Read What’s Up With Orthodox Men and Women and the Handshake

How to Be Modest and Elegant

Women tell me this can be both the most rewarding and the most challenging mitzvah for them to roll into. Rewarding, because they find it liberating and dignifying. Challenging, because shopping for good clothes gets a lot more complicated.

I asked my wife and daughters for any guidance they would give women who want to dress modestly and look good. Here’s what they came up with:

  1. Shop in the fall, when the clothing is modest and light enough for spring summer as well.
  2. Invest in classic, versatile pieces that can be worn repeatedly in different ways. Like a capsule wardrobe.
  3. Learn from friends who dress well. Don’t be afraid to ask them where they shop.
  4. Order online. A little tricky with boutiques that target the orthodox market because of their strict return policies, but some websites are easier.
  5. No need to change your entire wardrobe overnight. Like everything else, take it step by step.
  6. Wear clothes that make you feel beautiful, confident, royal, and most of all, clothes that feel like you. The “you” that you want to shine.
  7. Modesty is an investment and G‑d is your partner. It can be expensive, but you make back far more than you put into it.