So what makes a good letter? Let’s break it down

An encouraging letter, at its best, is not complicated. It is thoughtful, personal, and sincere. Often, it follows a gentle rhythm that helps the writer stay focused and the reader feel seen. In this chapter, we will break down that rhythm so you can write letters that are not only heartfelt, but also easy to create consistently.

The Five Essential Parts of an Encouraging Letter

Most effective encouraging letters include five simple elements:

1. A warm greeting
2. A personal connection
3. A message of encouragement
4. A word of hope
5. A thoughtful closing

Each part plays a role, and together, they form a complete expression of care.

Let’s walk through each one…

1. The Warm Greeting

The greeting sets the tone and signals whether the message will feel distant or personal.

It’s best to avoid overly formal or generic openings when possible. Instead of “Dear Sir or Madam” or even just a name with no warmth, aim for something that reflects a relationship. Some examples are:

• Dear Sarah,
• Dear Mr. Thompson,
• Dear Aunt Maria,
• Dear Daniel and family,
• Hello, my friend,
• Dear Sister in Christ,

A small addition of warmth can make a large difference. Remember that when the person is opening the letter, especially if it’s the first one they have received, they may be feeling confusion or anxiety about what the letter may contain. A warm and friendly greeting is the icebreaker and encourages them to continue reading.

2. The Personal Connection

This is where your letter becomes theirs. A good encouraging letter always includes something specific about the recipient.

It might be:

• A recent event in their life
• A shared memory
• A personal strength you’ve noticed
• A detail you remember from a conversation
• A meaningful milestone

Some examples of what they can sound like are:

• “I was thinking about our conversation last Sunday about your new job and wanted to follow up.”
• “I still remember the kindness you showed my family last summer during a difficult time.”
• “I heard about your recent surgery and wanted to check in on how you’re doing.”

This is where encouragement becomes personal rather than general, and is the first clue to the recipient as to what your intention is in writing to them.

Often, I write to strangers I have never met and know nothing (or little) about them. In these situations, I try to draw on a shared experience, such as the seasons, shared faith or community, or upcoming holidays. I also introduce myself right away and state my intention clearly so as not to add to any potential confusion or to cause alarm as to why someone they don’t know is writing to them. That opening line can sound something like…

• “I am writing to you to remind you that…”
• “I want you to know that you are loved…”
• “As part of a personal project of mine, I am writing…”
• “I felt God place it on my heart to…”

3. The Message of Encouragement

This is where you affirm, strengthen, and uplift the reader.

Encouragement can take many forms, such as affirming character, recognizing effort, acknowledging difficulty, expressing gratitude, and offering reassurance. The key is sincerity, not exaggeration, empty praise, or clichés.

Instead of writing “You’re amazing and perfect in every way,” you might write, “I’ve always appreciated your steady kindness and the way you make people feel welcome.” Instead of “everything will be fine,” try “I know things feel uncertain right now, but I’ve seen how strong you are through other difficult seasons.”

Encouragement does not have to deny reality. Rather, try to uplift the person by recognizing what they have or know. I see it as helping them lift their gaze a little higher to something more hopeful instead of trying to blindfold them with a pretty picture. From our personal experiences, we know that insincerity or an attempt to dismiss our feelings can lead to more harm than good. Finding the right words can be a challenge at times, but drawing on how we know we would like to be spoken to or encouraged is a great place to start.

I am often reminded of 2 Corinthians 3-4 on this topic: “Praise be to the God and Father of our Lord Jesus Christ, the Father of compassion and the God of all comfort, who comforts us in all our troubles, so that we can comfort those in any trouble with the comfort we ourselves receive from God.”

The God of all comfort that we worship is ready to equip us to comfort others. What a great help to have readily available for times when we don’t know what to say!

4. The Word of Hope

Hope is what gives encouragement and forward movement. It gently points the reader toward something beyond the present moment. For people of faith like us, hope will often include Scripture or reminders of God’s presence. For a broader audience, hope may simply be expressed through kindness, affirmation, or belief in their future strength (which will probably overlap with Point 3, so if you find that you’ve already shared something hopeful, there’s no need to repeat it!)

We may be people of faith, but that may not be true of the people we are writing to, who may not even know about the Bible and what it’s about. I always encourage my fellow letter-writers not to simply write “You need Jesus!” but instead to find a gentler way of pointing them towards the love and care of Christ. I lean towards a cautious approach as, in time, I hope to find the opportunity to express their need for God more clearly, but that can require greater trust and a deeper relationship with the person I am writing to. In my waiting for that opportunity, I can pray earnestly that God surround the person with love, care, and His truth. If I don’t expect to be writing to that person again due to circumstances or limited opportunity, I still try to be cautious in my approach, as the last thing I want to do is leave them feeling hurt or resistant to future conversations about faith.

Some examples of a gentle way to share words of hope can be:

• “I’m praying that you’ll find moments of peace this week, even in small ways.”
• “I know that brighter days are ahead for all of us.”
• “I hope you feel surrounded by care as you continue through this season.”
• “May you be reminded that you are not walking alone.”
• “Your situation made me think of this story in the Bible where… May you also experience…”
• “In times like these, I like to read my favorite Bible verse, which I hope will encourage you too… It can be found in a part of the Bible called Corinthians, where a man called Paul is writing to …” (Writing to someone who may have little to no knowledge of the Bible? If you’re going to share a verse or Bible story, introduce it and add context to help them understand why you felt like it was relevant to share!)

5. The Thoughtful Closing

The closing is your final impression. It should feel warm, sincere, and consistent with everything you’ve written. Avoid abrupt endings or overly formal sign-offs when writing encouragement.

Some examples I’ve used before are:

• With care,
• Thinking of you,
• With warm regards,
• Praying for you,
• Gratefully,
• In friendship,
• Blessings to you,

Then add your name in a way that feels personal. Even something simple like signing your first name can make the letter feel more intimate and genuine.

If I don’t know the person I am writing to well, I avoid adding hearts or anything that could be misinterpreted. This is something that is good to keep in mind if you are a woman writing to a man, or a man writing to a woman! Over the years that I’ve written to male individuals incarcerated in the US, I often sign off with both my name and my husband’s name (even if my husband isn’t directly involved in the letter writing) so as to avoid any confusion about my intention. Another way to use this approach can also be to include your partner or spouse earlier in the letter, such as “Chris was asking how you’re doing…” or “Mark says hello! He’s excited to hear more about…”

Both of these approaches are things that should be considered in order to encourage healthy boundaries between yourself and the person you are writing to, at least in the initial stages of your relationship.

Common Mistakes to Avoid

As you begin writing regularly, be aware of a few pitfalls:

1. Overusing clichés: Phrases like “Everything happens for a reason” can feel dismissive if not used carefully.
2. Making it about yourself: While sharing experiences can help, the focus should remain on the recipient. Similarly, we need to make sure that what we are sharing about ourselves doesn’t come across as boasting or pride. In my letters to incarcerated individuals, I try to be even more aware of this, as I have the privilege of many freedoms that they currently do not.
3. Offering unsolicited advice: Unless appropriate, encouragement is more powerful than instruction.
4. Being overly vague: General statements are easy to write but hard to remember.
5. Writing too formally: Warmth is often more meaningful than polish!

Did I miss anything? Let me know what you consider a good encouraging letter, and I can add you as a contributor to this Substack article!