A guide to Elul, Rosh Hashanah, Yom Kippur, and the practical work of teshuva

ELUL — The Final Month of the Jewish Year

Elul is the final month of the Jewish year — a time set aside at the end of our yearly cycle for each of us to pause, take stock of how we are living, and clarify what adjustments we need to make so that we end our year, and begin the new year, Rosh Hashanah, in the best possible way.

The Shofar's Wake-Up Call

In shul, the daily blasts of the shofar act as a spiritual alarm clock, reminding us that Rosh Hashanah and Yom Kippur are approaching. To really understand the opportunity of this month, we need to understand the essence of Rosh Hashanah and Yom Kippur - which is what this month is preparing us for - so please keep reading.

Yemei Ratzon — The Days of Divine Desire

The entire month of Elul has been imbued by Hashem with an extraordinary blessing — what our sages call Yemei Ratzon, the "Days of Divine Favour." As the verse says, "I am to my Beloved, and my Beloved is to me" — Hashem makes Himself especially close and available, even though we ourselves may be creating blocks, and He wants to help us.

In earlier generations, when the chazzan - prayer leader - would announce "Rosh Chodesh - the new month of Elul is coming," a sense of awe would fill the room. It wasn't fear of punishment — it was fear of missing the opportunity. Imagine being given a fixed amount of time to prepare for an amazing year, with all the help you need, and knowing that your year ahead will be shaped by how you use this month. You'd want to use it well.

That's Elul.

ROSH HASHANAH — Facing in the Right Direction

The way we see life — our paradigm — affects everything: What we understand to be valuable, and therefore, what we work towards and how we spend our time. If our values and goals are clear, it is easier to fill our days with pursuits that matter. But if we lose sight of the bigger picture, it's easy to get caught up in the small stuff and reach the end of a season, or even a lifetime, realising we were aiming at the wrong goals and now we are left with very little of significance and a lot of regrets.

The Chofetz Chaim illustrated this with a story.

A man once heard about a far-off island where diamonds lay scattered on the ground, free for the taking. The only catch: it took a year to get there, a year to gather treasure, and another year to sail home.

When he arrived, he bent down to pick up a diamond — but the locals laughed. "That's worthless here. We use fish oil as money." It was true. So he learned the fish oil trade, worked hard, and became wealthy — by the island's standards.

After a year, he filled barrel after barrel with fish oil and loaded them onto the ship. But on the long voyage home, the oil went rancid, and by the time they docked it all had to be thrown overboard. As his home port came into vision and he remembered the dilapidated home that he had left behind to seek his fortune, his memory was jolted — he suddenly remembered why he had come, and how somehow he had replaced his goals with the goals of those on the island. His heart sank.

When he arrived home, his wife found a handful of diamonds in his coat pocket, gathered absentmindedly during his first days on the island. Her face lit up: "You did it! We're rich!" He forced a smile, but thought: If only I had remembered my true mission, I could have brought home so much more.

The Essence of Rosh Hashanah

That's what Rosh Hashanah is about: remembering why we came into this world, and reconnecting to that mission as our big picture. Life offers endless "fish oil" opportunities — things that seem valuable in the moment but pale into insignificance in the light of eternity. Rosh Hashanah calls us back to the diamonds: the truth that there is a Creator, Hashem, Who is real, Who directs the world, and Who has a purpose for history and for each of us — Who gives the opportunity to choose truth and meaning and bring this spirituality into the physical world that we live in. 

When we keep that focus, our time and energy go into things that bring us deep meaning in the present and that last for eternity. When we lose our clarity, we risk spending our lives stockpiling fish oil that we can't take with us.

Teshuva Starts With the Big Picture

Rosh Hashanah is the first two days of the Ten Days of Teshuva (teshuva means "returning," or "realigning"); Yom Kippur is the last of these ten days. If teshuva is about fixing mistakes, why don't our Rosh Hashanah prayers focus on admitting any specific mistakes, which is what we do on Yom Kippur? One reason is that we can't begin to focus on the details of the ultimate goal before we have the ultimate goal clear.

If we understand the point of life as the opportunity to acquire really nice physical things, we haven't got the big picture, the purpose of our creation, our ultimate goal clear. This world is an opportunity for us to use our power of choice - of free will -  to choose that which is truly valuable - love, integrity, holiness... When we leave this world we are nothing other than the sum total of our choices. The values that we are choosing each day forms who we will be for the rest of eternity.    

Rosh Hashanah tunes us into the big picture, the reason for our creation. A few questions to ask ourselves on Rosh Hashanah and the days leading up to it are: Do I see Hashem as my God, my Father and King and myself as Hashem's beloved child? Do I understand the purpose of creation, the goal? Do I understand that I can gain more and more clarity on the goal and how to achieve it simply by seeing How Hashem communicated this to us in His Torah - His instruction manual for living? 

At the heart of Rosh Hashanah is one mission: to choose Hashem as King. Not just believing He exists, but taking Him seriously, welcoming His guidance, and putting His truth and purpose for us and the world at the centre of our lives. Crowning Hashem means choosing meaning over emptiness, clarity over confusion, connection over disconnection — saying, "Hashem, I recognise You as my King and I hope for the day when the entire world will recognise You."

Think of it like a yearly review with the CEO of your company. They want to invest in you — but you need to be committed to the mission, clear about your direction, ready to take the next step. That's Rosh Hashanah. How we "show up" over these two days sets the spiritual DNA of the year ahead.

Rosh Hashanah is not require us to turn up perfect, free of any misdemeanours and flaws. If we can, great! But it can take a long time to become perfect. Rosh Hashanah is about making sure we are pointing in the right direction, committing to the right goals starting with whatever is the next most appropriate step. We want to make sure that we're working towards the diamonds — and not getting distracted by the fish oil, which we can't take with us.

YOM KIPPUR — Working on the Details

If Rosh Hashanah is about setting the big picture, Yom Kippur is about beginning to align the details of our lives with it.

The Shema begins with the big picture — accepting Hashem as King. The second paragraph starts to focus on the details — the mitzvot - Hashem's guidelines for living. The order is deliberate: big picture first, then details. That's the flow of the High Holidays too — Rosh Hashanah is "Hashem, I accept You as My God, My Father and My King. I'm committing to Your vision for the world!" Yom Kippur is where we start working on the specifics of what that practically means.

The basic parts of teshuva are simple: recognising what needs repair - where our life choices are not ideal - feeling genuine regret the consequences of our choices, verbalising it before Hashem, and committing not to repeat it — or, where that's not immediately possible, committing to a real plan to get there over time.

One thing worth knowing now: Yom Kippur cleanses only that which pertains to between us and Hashem. Hurt or damage we've caused to another person needs to be made right before Yom Kippur — apology, repair, reconciliation — because Yom Kippur doesn't wipe away those debts without action. (More on exactly how, below.)

You Don't Have to Fix It All at Once

In the Torah, on the 1st day of the Jewish month of Nissan, Moshe communicates a message from Hashem for His special nation the Jewish people. The message was to bring the Pesach offering in about 2 weeks on the 14th of Nissan. The verse says they did it - seemingly implying that they brought it then and there on the 1st Nissan - yet we find out later in the Torah that they did actually only bring it two weeks later, on the day that it was due. Why does the Torah make it sound as if it the Jewish people brought the offering straight away and not 2 weeks later when it was due? Rabbeinu Yona teaches us that this is to communicate that once they truly committed to bring the offering, it was counted as done.

This is a life-changing principle: when we commit with sincerity, choose our next clear step, and set ourselves up with real support to follow through, Hashem counts it as if we've already achieved it — even if what we are working towards can't be achieved in one day and may take some time.

The Roots

Real teshuva requires one to look beneath the surface at why they are choosing what they are choosing. A repeated behaviour — say, speaking negatively about others — usually grows from something unhealthy, be it insecurity, a need for control, jealousy or something else. Learning to guard one's speech is the surface fix; understanding where it's coming from is where lasting change begins. Teshuva isn't about fixing everything at once — it's about uncovering one root at a time, and taking one achievable step forward.

Rosh Hashanah is about making sure we are valuing the right things, that we are pointing in the right direction. Yom Kippur is about admitting what parts of our life don't fit in this, regretting that and committing align oneself, one step at at time, even if it will take quite a lot of steps and quite a  bit of time. And, as we explained, when we admit, regret, and truly commit — even if full change takes time — Hashem sees it as if we've already reached our goal, braucse us getting there is only a matter of time.

So how does doing Yom Kippur teshuva which is teshuva for the details that aren't aligning with our purpose work in practice? There are two relationships to put right: the one between us and Hashem, and the one between us and other people.

TESHUVA BETWEEN YOU AND HASHEM — The Practicalities

Some mistakes are things we did that we shouldn't have. Others are things we didn't do that we should have. How do we do teshuva for these?

1. Admit. Before we can regret a mistake or commit to change, we first have to honestly admit we erred, rather than rationalise it away. That honesty takes courage — but it's the prerequisite for everything that follows.

2. Feel genuine regret. Think about why the mistake wasn't appropriate, and how it has limited or hurt you and is delaying the ultimate happy ending of world history. This is uncomfortable, but necessary.

3. Commit to change — even when it's a habit. Some things you can commit to never doing again with real confidence. Habits take longer. Either way, teshuva counts: commit to a real plan that will eventually get you there — starting with the first step, track your progress, and give yourself credit for starting.

4. Verbally confess. Verbally confessing your regret and commitment, out loud, before Hashem.

The Rambam gives a text of how one can do this:

"I implore You, Hashem, I have sinned, I have transgressed, I have committed iniquity before You by doing (or not doing) the following: ______. Behold, I regret and am embarrassed by my deeds. I promise never to repeat this act again — or, at the very least, I sincerely commit to a plan that will eventually get me there."

One reminder: You are a diamond! The mitzvah of teshuva is not about making ourselves feel worthless. That would be a huge mistake! Our essence — our neshama — is a holy soul, made in the image of Hashem. Teshuva is like removing gunk which has become attached to a diamond: however much gunk has built up, it doesn't change the value of the diamond underneath. It just hides its beauty.

Ready to put this into practice? Please check out the following exercises:

TESHUVA BETWEEN MAN AND MAN — The Practicalities

Yom Kippur only cleanses what's between you and Hashem. If you've hurt, embarrassed, taken from, spoken about, or let down another person, that needs to be rectified separately regarding the person or people affected. Speaking out our admission, regret and commitment for the future to Hashem can not cleanse us for misdemeanours that have transpired between ourselves and others until we have rectified those things with those people. This needs to be done as soon as possible but certainly BEFORE Yom Kippur. 

Yom Kippur only cleanses wrongs between people once:

1. Any real damage has been rectified — money or things returned, any harm done is undone.
2. The person's forgiveness has been received.

When to do this: as soon as you realise you've wronged someone — the sooner the better! If you haven't gotten to it yet, the days leading up to Yom Kippur are an especially powerful and appropriate time to ask.

How to ask forgiveness. Go in person, write a message, or — if it's too hard to go yourself — ask someone else to approach them for you. If you genuinely can't be explicit about what happened, a sincere general version is good:

"It's Yom Kippur in a few days, a time to ask for forgiveness in case a wrongdoing was done during the year. In case you have done anything to me, I of course forgive you… and if I have done anything against you, could I ask you to forgive me?"

If a situation feels genuinely complicated, it's worth speaking to a Rav for clarity.

Ready to put this into practice? Please check out the exercise below:

FORGIVING OTHERS

Just as it's important to ask for forgiveness when we've wronged someone, it's a core part of the season to give forgiveness when others have wronged us — for two real, practical reasons: Hashem deals with us as we deal with others, so we want to be quick to forgive; and carrying anger and hatred is unhealthy — it can weigh on you rob you of your day to day quality of life.

A general statement of forgiveness. One especially important exercise before Yom Kippur: make a sincere, general statement forgiving anyone who has wronged you this year, whether or not they've asked. For instance:

"I forgive anyone who's hurt me this year, knowingly or not."

You can find texts written to verbalise our forgiveness of others in an ordinary siddur - prayer book -and in a Yom Kippur machzor - prayer book. In a Siddur there is a paragraph in the nightly bedtime Shema prayers beginning "Master of the Universe, I hereby forgive anyone who…", that can be said. In the Yom Kippur machzor there is a paragraph near the very beginning in the prayer called Tefilla Zakah beginning "Since I know…"

Reach out, where it would help. For most things, forgiving privately is enough. But if it's someone you're still in a relationship with, and the issue has gone on too long and there are less than ideal vibes between you, reaching out and settling it can be a real act of kindness for both of you.

There are rare cases where forgiveness isn't required — but that's the exception, not the rule. If a situation feels genuinely difficult, it's worth speaking to a Rav for clarity.

Ready to put this into practice?

EXERCISES