How to Overcome the Big Send Anxiety: What SaaS Email Marketers Recommend

Hitting send on an email campaign can make anyone feel on edge. “The big send anxiety” affects newbies and seasoned marketers alike.

An email mistake can feel like a catastrophic event.

We talked to 12 SaaS email marketers about anxiety reasons, the worst mistakes they’ve made, their pre-send checklists, and tips to overcome the fear. Here’s what they shared.

What drives email sending anxiety? What are marketers afraid of?

Email and workflows have a long list of moving parts that it’s common to feel overwhelmed and fear that you might miss something. Our respondents share what makes them worry before hitting send:

Typos and content errors

Some email marketers get a bit anxious about typos, but Alan Harris of TLDR says it’s a minor offense compared to other mistakes:

“A typo is unfortunate but not even the biggest error that can happen, especially in B2B SaaS. Worse outcomes could be anything from sharing incorrect information, accidentally including a ‘do not contact’ or low-quality segment, or a broken CTA link.”

Broken links

Head of Email creator Devin O’Toole explains how missing a broken link affects both readers and the sender:

“Broken links are frustrating because they disrupt the user experience. Whenever you have to do a re-send, it not only creates extra noise in the inbox, it makes reporting on things like click rate a lot more challenging.”

Getting the send time wrong

CaaSocio co-founder Aiza Coronado shares that potentially messing up the send schedule can affect performance:

“If it’s a sales campaign, my anxiety is around whether I scheduled it correctly (hello timezones). I’m paranoid because even a small miss can affect performance.”

Sending an email right away

Emails Done Right founder Samar Owais shares that sending an email immediately after a review makes her anxious:

“My anxiety peaks anytime I’m sending out an unscheduled email. I HATE sending out an email immediately after it’s finalized. Part of my process is to ‘sleep’ on my emails. It isn’t until I see them with fresh eyes that I pick things that I would have otherwise missed.”

Segmentation errors

Since there’s no way to unsend emails, sending an email to the wrong segment might cause confusion with readers or potentially get them to unsubscribe or report your emails as spam.

James Lamb explains why he fears making this error:

“I fear putting someone in the wrong segment or putting them in two segments. Or sending a split test and one of the splits has the wrong audience.”

Samar also shared that she’s nervous about committing this mistake with folks in the welcome sequence:

“The other thing that makes me anxious is sending emails to folks who’re still in the welcome sequence — that’s the worst email offense I can make as an email marketer.”

Deliverability

Suped co-founder Michael Ko shares that he’s worried about deliverability issues that could tank their domain:

“A busted domain reputation takes weeks to fix. My anxiety spikes over deliverability. I worry that a DNS change we made last week quietly broke our SPF record. I have spent enough time staring at DMARC failure reports to know exactly how fast an unaligned campaign can tank a domain.”

Auroriele Hans of AuthorityScribe explains that she’s worried about this for larger sends because the effects scale with volume:

“For larger sends, I’m more worried about deliverability because issues like hard bounces, spam complaints, and low engagement scale with volume.”

No second set of eyes to check the email

An email could have so many elements so there’s extra pressure if you’re doing the pre-send QA process alone. Aerin Paulo shares why having no second set of eyes spikes her anxiety:

“I’ve been a team of one either literally (just me) or in practice (nobody has time but me) — I’ve looked at this so many times now I’ve stopped seeing words that resemble English, so does that mean I’m going to miss something? Did I remember to check mobile? Does this look okay to users on dark mode even though I don’t like it (but there’s not much I can do while also following brand guidelines)?”

Holding yourself to an imagined expert standard

Emailmonday founder Jordie van Rijn says that holding ourselves to an expert standard we made up for ourselves drives the anxiety and causes us to overthink:

“What would people think? Is it good enough? Is it providing enough value? Because you imagine everyone being critical and going through your words with a fine-tooth comb. And as an email marketing specialist that feels doubly true. Both the content AND the email. It should be up to some ‘expert standard’ we make up for ourselves.

The truth is: you are probably the one who cares the most about your own writing and emails.”

SaaS email horror stories and lessons learned

For some email marketers, their hypothetical worst scenario became real. While unfortunate, these experiences taught them some valuable lessons:

Wrong details slipped past three reviewers

Aerin recalls the time when wrong details in an event email made it past three people:

“Sending the wrong details out in an event email. It did happen once, and in that instance it made it past three sets of eyes with the mistake. We’re only human.

Thankfully it was correct everywhere but one paragraph, and oops emails tend to do pretty well, so it worked out okay.”

Sending a blank email to 500k subscribers

Alan shares how an accident turned into the biggest mishap of his career:

“My biggest f-up in my lifecycle marketing career was when I was on the B2C side and working with send volumes in the millions. I accidentally sent an email to half a million subscribers that was entirely blank — no content whatsoever.”

VIP dinner invite sent to a broader list

Alan also recounts how a colleague accidentally sent an exclusive invite to a broader list, and everyone got in trouble for it:

“The biggest secondhand f-up I’ve heard of from a colleague was an email marketer sending invites to a VIP dinner for a field event targeting decision makers at enterprise orgs. They apparently accidentally sent it to a much broader list, which included junior roles and small companies outside their ICP, which quickly filled up the RSVP list. Everyone from the email marketer to the head of field marketing got in trouble for that one.”

Getting a 100% bounce rate

Michael Ko shared how missing a crucial step resulted in a 100% bounce rate:

“I lived the nightmare at my last company. We finally tightened our DMARC policy to reject to stop spoofing. The problem is we forgot to authorize our marketing automation platform first. We hit send on a major product announcement and Google and Yahoo flat out rejected every single message. The open rate sat at absolute zero.

I spent the next 48 hours in a panic trying to decipher cryptic XML reports just to figure out what broke. I learned that managing email infrastructure manually is a trap. You miss one DNS text record and you are completely invisible.”

Exclusive offer sent to a broader list

SaaS Playbook author Etienne Garbugli learned the importance of running through checklists with this incident:

“We sent 100k free subscription offers instead of 500. I learned the importance of running through checklists before hitting send.”

Forced email re-send deflating an exciting moment

Devin shares a time when a collaborator asked them to do some minor wording changes and a re-send:

“I usually don’t expect or anticipate mistakes. But of the ones that have happened, one of the more frustrating ones was related to a high-profile marketing collaboration that was sweeping across social media — and unexpectedly involved our product.

Since we didn’t know it was happening, our marketing team scrambled and quickly published supporting content across all our channels. Except — after the email went out — one of the companies involved in the campaign insisted we re-send the email with a few minor wording changes. Our users were not only annoyed at receiving multiple messages, but confused as to why we re-sent it. It deflated what should have been an exciting moment.”

After this incident, their team is became more cautious about reactive marketing:

“While it was a rare occurrence, it taught us to be more cautious with reactive marketing, particularly in email. It’s easy to change a blog post or delete a social media story, but you can’t unsend an email.”

Pre-send checklist

While their actual pre-send checklists look very different, most email marketers include these steps before an email or workflow goes out:

Step 1. Check the email content

Scan or read through the email content to catch typos and confirm details.

Alan says that you could also use AI if you’re doing the QA process solo:

“One great AI use case for busy marketers and smaller teams is using LLMs for QA. Share a screenshot of your email with your LLM of choice and it will flag typos, copy suggestions, etc.”

Some email marketers go the extra mile and read it aloud. Michael Wilding shares why:

“Read aloud the subject line, preview text and email body copy. It is important to read it aloud because it forces you to read every word and prevents you skimming over the content and seeing what you think should be there.”

Step 2. Send a test email

Most email marketers send a test email to themselves, and/or their teammates to check what the actual email would look like to recipients.

Step 3. Check the web and mobile view

Review the formatting by viewing the email on a desktop and mobile device at the minimum. You may also use an email preview tool for this step.

Step 4. Check every link

Click on every link and CTA, including the unsubscribe button, to check that they’re working and to confirm that they’re redirecting to the right place.

Step 5. Check the recipient segment

Double or triple check the recipient field contains the right segment.

Step 6. Schedule the email to go out at a later time

This lets you take a step back and do your QA process calmly and thoroughly.

Tips on overcoming email send anxiety

Create your segments first

Etienne advises that you should create your segments first before adding messages:

“Create segments first. Watch who passes through them. Adjust. Only then start adding messages.”

Get your authentication locked down

Michael Ko stresses that you should also look at your headers:

“Stop obsessing over the perfect subject line and start looking at your headers. You can survive sending a broken link. You can survive a typo in the first paragraph. You cannot survive hitting the spam folder on every send. Get your authentication locked down. Put a tool in place to monitor your reports so you actually know what happens after you hit send. Once you know your infrastructure is bulletproof, hitting that button gets a lot less terrifying.”

Build a thorough QA process

Alan shares that a QA process will give you the confidence to hit send:

“Every email marketer has at least one story of a big f-up they were directly or partially responsible for, but a thorough QA process will give you the confidence to hit send without fear.”

Always schedule, never use “send now”

Michael W. advises scheduling so you’re not rushing:

“Schedule your messages at least an hour in advance to give yourself time to do everything calmly. If you are rushing to send an email then you are more likely to make mistakes.”

Devin shares the same sentiment:

One big rule I have is never use ‘Send Now.’ ALWAYS schedule. Scheduling means you are prepared — sending now means you are in a rush. I spent years working as an editor, and I can confidently say that rushing leads to more mistakes. Even if you need to schedule it 10 or 15 minutes from now — this gives you a chance to step back, give it a final look, and pause it if needed.”

Gain knowledge and experience

Auroriele says that you should arm yourself with knowledge to minimize risks. She adds that experience will help build more confidence:

“Knowledge is the best way to combat your fears. Learn the steps to minimize the risk of large sends: keep your list clean, personalize your message and offers, and drip out large sends to different portions of your audience over time. Just like anything else, experience successfully pulling off big sends will make you more confident.”

Own up to your mistake

If you do make mistakes, Aerin says owning up and apologizing because readers will appreciate it:

“Deep breath. There are no marketing emergencies. You did your best, and if you made a mistake, be real with your audience — they sincerely appreciate it 9/10 times.”

Learn from your mistakes

Samar reminds us that mistakes will be part of the journey to becoming a better email marketer:

“Do your due diligence then put your big girl or boy pants on and hit send. And if you mess up? It’ll make you a better email marketer. You’ll be in good company. Every seasoned email strategist’s QA checklist or process is built on the mistakes they made. Those processes and checklists are battle-tested for a reason.”

Meanwhile, Aiza advises to fix mistakes fast, learn from them, and don’t let these incidents stop you from sending:

“No matter how experienced you are, mistakes can still happen. I mean, we’ve all gotten those empty test emails from HBO, right? It’s not the only one. I’ve received a couple wrong emails, even from really solid brands. But that doesn’t mean we get careless.

My operating principle: get it right the first time as much as possible. But if something breaks — fix it fast, learn from it, and move on. And most importantly — don’t let one wrong send define your entire email career. Keep on sending.”

Embrace the fear

James shares that instead of overcoming the fear, you should recognize and embrace it because it shows that you care about your work:

“When you lose the fear, you make mistakes. Recognize the fear or anxiety as a beneficial force. Slow down. Take a breath. Double or triple check if it helps.

I don’t do as many deployments these days, but when I did, I used to stop and say a quick prayer for the recipients. I wasn’t praying for my campaign or my company, but it was a quiet moment before pressing the button, acknowledging I was able to do something to impact countless people out there in the world living their lives.

Find something — a few pushups, a run up and down a flight of stairs, four slow sips of coffee, a cookie — any completely optional ritual between pre-flight and pressing the button that creates a moment of zen for you.

But embrace the fear, acknowledge the anxiety, take a breath.”

Embrace the uncertainty

Jordie says that we should take comfort in the fact that we’re all still learning:

“If you are anxious about whether you are doing it right and if the email will have the expected results, then take comfort that nobody really knows for sure. We are all learning.”

That email is rarely as high stakes as we think

Rachael Pilcher of Mighty Fine Copy shares what personally helped her is reframing how she thinks about the email’s impact:

“What actually helped me most was recognizing that an email is rarely as high-stakes as my brain insists it is. Most people read your email once, get the gist, and move on with their day. They’re not forensically analyzing your word choices the way you are.”

Insights from SaaS email marketers

James Lamb

James Lamb shares that his sending anxiety is mainly driven by potential mistakes in segmentation:

“Making a mistake in segmentation. Specifically, I fear putting someone in the wrong segment or putting them in two segments. Or sending a split test and one of the splits has the wrong audience.”

To prevent those mistakes, he relies on a checklist in Google Sheets that does the math for him:

“It produces the asset names and adds up segment counts so you know you’ve selected correctly. When splitting audiences, try to make each audience different (for example 50,001 + 49,999 instead of 50,000 + 50,000) — too small to ruin statistical significance but much clearer that you’ve got the correct audiences.”

His advice for fellow email marketers? Befriend the anxiety:

“When you lose the fear, you make mistakes. Recognize the fear or anxiety as a beneficial force. Slow down. Take a breath. Double or triple check if it helps.

I don’t do as many deployments these days, but when I did, I used to stop and say a quick prayer for the recipients. I wasn’t praying for my campaign or my company, but it was a quiet moment before pressing the button, acknowledging I was able to do something to impact countless people out there in the world living their lives.

Find something — a few pushups, a run up and down a flight of stairs, four slow sips of coffee, a cookie — any completely optional ritual between pre-flight and pressing the button that creates a moment of zen for you.

But embrace the fear, acknowledge the anxiety, take a breath.”

AuthorityScribe

AuthorityScribe founder and email strategist Auroriele Hans shares that her anxiety shifts depending on the size of the send:

“I’m usually a bit anxious about typos slipping through on smaller sends. For larger sends, I’m more worried about deliverability because issues like hard bounces, spam complaints, and low engagement scale with volume. List hygiene helps keep bounce rates low, and spam complaints and engagement are usually better managed by sending relevant content to the right people at the right time.

So even on large sends, I’d segment and use conditional content. I’d also use a workflow to drip the send out to different segments over time instead of sending everything at once.”

When asked about the hypothetical worst case scenario, she fears that her client might get quarantined for a spike in bounces or complaints:

“The worst outcome would be getting quarantined because of a spike in bounces or spam complaints, which could tank my client’s sender reputation and cause future emails to land in the spam folder. Fortunately, this hasn’t happened to me.”

Auroriele relies on segmentation and a system that routinely cleans her client’s email list:

“I have systems in place like integrating my client’s ESP with email validation tools, so their list gets scrubbed continuously. When I’m planning the email, I look for ways to segment the audience and personalize with conditional content. Large sends always get broken up and dripped out via a workflow.”

She believes the best way to combat fear is to learn your way out of it:

“Knowledge is the best way to combat your fears. Learn the steps to minimize the risk of large sends: keep your list clean, personalize your message and offers, and drip out large sends to different portions of your audience over time. Just like anything else, experience successfully pulling off big sends will make you more confident.”

Aerin Paulo Marketing

Aerin Paulo, founder and principal strategist of Aerin Paulo Marketing, shares that her anxiety stems from having to review different aspects of the email all by herself:

“I’ve been a team of one either literally (just me) or in practice (nobody has time but me), so it’s really that pressure of ‘I’ve looked at this so many times now I’ve stopped seeing words that resemble English, so does that mean I’m going to miss something? Did I remember to check mobile? Does this look okay to users on dark mode even though I don’t like it (but there’s not much I can do while also following brand guidelines)?’”

She shared that the worst case scenario did happen, with the wrong details making it past three set of eyes before going out:

“Sending the wrong details out in an event email. It did happen once, and in that instance it made it past 3 sets of eyes with the mistake. We’re only human. Thankfully it was correct everywhere but one paragraph, and oops emails tend to do pretty well, so it worked out okay.”

While nothing really removes the anxiety, Aerin has her FCLM list in place:

“Nothing removes that what if anxiety for me, but I like to do an FCLM list — Formatting, Content, Links, Mobile. I check for weird spacing and colors, then read the email (out loud when possible) to myself, then click the links to confirm they’re going to the right place, then do a pass on mobile for formatting.

HubSpot is especially fun on mobile because if you weren’t the original creator of an email and you forget to check mobile, sometimes there are surprise elements or pictures in your email.”

She also reminds us that if you make a mistake, everyone will sincerely appreciate your apology:

“Deep breath. There are no marketing emergencies. You did your best, and if you made a mistake, be real with your audience — they sincerely appreciate it 9/10 times.”

TLDR

TLDR senior growth marketer Alan Harris shares he’s more concerned about mistakes that have real downstream consequences:

“A typo is unfortunate but not even the biggest error that can happen, especially in B2B SaaS. Worse outcomes could be anything from sharing incorrect information, accidentally including a do not contact or low-quality segment, or a broken CTA link.”

He shares two horror stories: one about sending a blank email to half a million subscribers and the other one about sending an exclusive invitation to a broader list:

“My biggest f-up in my lifecycle marketing career was when I was on the B2C side and working with send volumes in the millions. I accidentally sent an email to half a million subscribers that was entirely blank — no content whatsoever.

The biggest secondhand f-up I’ve heard of from a colleague was an email marketer sending invites to a VIP dinner for a field event targeting decision makers at enterprise orgs. They apparently accidentally sent it to a much broader list, which included junior roles and small companies outside their ICP, which quickly filled up the RSVP list. Everyone from the email marketer to the head of field marketing got in trouble for that one.”

Alan’s process starts with a small seed list and ends with another QA layer done by a colleague:

“First, QA it yourself with a real send (not a test email) to a small seed list. Scan the copy for typos, click every link, check renders in common email browsers with an email preview tool. If possible, have a colleague (1+ set of internal eyeballs is ideal) also QA it.

One great AI use case for busy marketers and smaller teams is using LLMs for QA. Share a screenshot of your email with your LLM of choice and it will flag typos, copy suggestions, etc.”

He shares that a thorough QA process will help you overcome the fear:

“Every email marketer has at least one story of a big f-up they were directly or partially responsible for, but a thorough QA process will give you the confidence to hit send without fear.”

Suped

Michael Ko, co-founder of Suped, shares that his anxiety spikes around deliverability:

“For me, it is rarely about typos. A typo is embarrassing, but a busted domain reputation takes weeks to fix.

My anxiety spikes over deliverability. I worry that a DNS change we made last week quietly broke our SPF record. Or that we forgot to authenticate a new sending tool and now a massive broadcast is going straight to the spam folder. I have spent enough time staring at DMARC failure reports to know exactly how fast an unaligned campaign can tank a domain.”

He shares that he experienced his worst case scenario at his last company:

“The nightmare is always a 100% bounce rate. And yes, I lived it at my last company. We finally tightened our DMARC policy to reject to stop spoofing. The problem is we forgot to authorize our marketing automation platform first. We hit send on a major product announcement and Google and Yahoo flat out rejected every single message. The open rate sat at absolute zero.

I spent the next 48 hours in a panic trying to decipher cryptic XML reports just to figure out what broke. I learned that managing email infrastructure manually is a trap. You miss one DNS text record and you are completely invisible.”

Before he hits send, he checks if they’re are clean on the auth side and if the segment is right:

“First, I check the actual audience segment logic twice. Then I send a test batch to a mix of personal GMail and Outlook accounts. I do not just look at how the design renders. I dig into the message headers to confirm SPF and DKIM pass and align with our domain.

If we are clean on the auth side and the segment looks right, I feel okay pulling the trigger. I’ll also typically run any flows or campaigns for a while in a test period with internal addresses only to test all the logic before opening it up to real segments.”

His advice for fellow marketers is to get their authentication locked down because it’s harder to recover from:

“Stop obsessing over the perfect subject line and start looking at your headers. You can survive sending a broken link. You can survive a typo in the first paragraph. You cannot survive hitting the spam folder on every send. Get your authentication locked down. Put a tool in place to monitor your reports so you actually know what happens after you hit send. Once you know your infrastructure is bulletproof, hitting that button gets a lot less terrifying.”

Michael Wilding

Michael Wilding says that his anxiety comes from three possible scenarios: a mistake in the content of the message, a link not working, and on complex segmentations, the wrong segment getting the wrong content.

He also shared that the worst scenario he imagined did happen but not in the way he expected:

“Broken links in the middle of a large product launch. It did happen, but not because the email link was broken — the website crashed due to the volume of traffic in a short period of time generated by email.

Stress test the landing pages during large launches for the maximum expected volume of traffic produced via email.”

Michael emphasizes the importance of reading everything aloud during your QA step:

“Do a test send and read aloud the subject line, preview text, and email body copy. It’s important to read it aloud because it forces you to read every word and prevents you skimming over the content and seeing what you think should be there.

Then click on every link in the message (including unsubscribes) to check if they’re working. During large launches, stress test the landing pages for the maximum volume of email traffic expected.”

He advises fellow email marketers to schedule messages at least an hour in advance:

“Schedule your messages at least an hour in advance to give yourself time to do everything calmly. If you are rushing to send an email then you are more likely to make mistakes.”

Head of Email

Head of Email creator and Bitly’s senior lifecycle marketing manager Devin O’Toole shares that mistakes happen but the effects can vary:

“Mistakes happen to all of us at some point. Most typos are easy to laugh off. I once left out a word in the subject line of an email all about copywriting best practices. It was embarrassing, but actually ended up resulting in a number of replies and opportunities to have one-on-one conversations. While I would never do it on purpose, mistakes like this can inadvertently make your brand feel more human and relatable.

Broken links are frustrating because they disrupt the user experience. So this is one I really don’t like to see happen. And whenever you have to do a re-send, it not only creates extra noise in the inbox, it makes reporting on things like click rate a lot more challenging.

But the worst mistakes are the ones that can cost a company in money or reputation. Things like legal issues, or accidentally listing the wrong sale price for something. I’m fortunate I don’t work with topics that venture into these territories too often, but when I do, I always make sure to get extra eyes on the message.”

He recalls a frustrating incident where miscommunication took the wind out of an exciting moment:

“I usually don’t expect or anticipate mistakes. But of the ones that have happened, one of the more frustrating ones was related to a high-profile marketing collaboration that was sweeping across social media — and unexpectedly involved our product.

Since we didn’t know it was happening, our marketing team scrambled and quickly published supporting content across all our channels. Except — after the email went out — one of the companies involved in the campaign insisted we re-send the email with a few minor wording changes. Our users were not only annoyed at receiving multiple messages, but confused as to why we re-sent it. It deflated what should have been an exciting moment.

While it was a rare occurrence, it taught us to be more cautious with reactive marketing, particularly in email. It’s easy to change a blog post or delete a social media story, but you can’t unsend an email.”

Devin’s one big rule is to never use Send Now for their emails:

“The main part of my proofing process is firing off a test send to myself, which I view on both mobile and desktop. (If it has dynamic content, I’ll send multiple versions to test the logic.) Double check everything — read it through multiple times, check the links, check the segmentation, scheduling, campaign settings, etc.

One big rule I have is never use Send Now. ALWAYS schedule. Scheduling means you are prepared — sending now means you are in a rush. Even if you need to schedule it 10 or 15 minutes from now, this gives you a chance to step back, give it a final look, and pause it if needed.”

He also emphasized that mistakes will happen and when it does, we should learn from it and move forward:

“We all make mistakes. ‘To err is human.’ Mistakes will happen in this line of work. When they do, figure out what you need to tweak in your process to prevent it from happening again, but keep your head up and keep moving.”

Mighty Fine Copy

Mighty Fine Copy founder Rachael Pilcher shares that getting the right tone drives her anxiety:

“I think that email sending anxiety is more common than people admit, and I say that as a professional copywriter who has genuinely reread a three-sentence email 17 times before hitting send.

For me, the anxiety usually looks like: Is the tone right? Did I sound too formal? Too casual? Should I have used an exclamation mark? Should I remove the exclamation mark? So by the time I’ve finished second-guessing myself, I’ve spent half an hour on an email that says ‘Sounds good, see you on Tuesday.’”

For her, the worst case scenario would be sending an important email with a bad typo:

“It would be something like hitting send on a really important email to someone, and then noticing there’s a typo so bad it will haunt you for the rest of your life. This has not happened to me…yet!”

Rachael asks herself three questions before hitting send:

“I stopped aiming for perfection. Copywriters especially can over-polish everything to the point of paralysis. For important emails, I ask myself three questions: Does it say what I need it to say? Is the tone right for this person? Would I be embarrassed if someone forwarded it? If it gets three yeses, I hit send.”

And what has helped her personally is a reframe about an email’s impact:

“What actually helped me most was recognizing that an email is rarely as high-stakes as my brain insists it is. Most people read your email once, get the gist, and move on with their day. They’re not forensically analyzing your word choices the way you are.”

SaaS Playbook

SaaS Playbook author and lifecycle email consultant Etienne Garbugli shares that his email pre-send anxiety is driven by targeting errors or variables not showing values.

The worst case scenario materialized for him but he learned an important lesson:

“We sent 100k free subscription offers instead of 500. I learned the importance of running through checklists before hitting send.”

He emphasizes the importance of creating segments first:

“Create segments first. Watch who passes through them. Adjust. Only then start adding messages.”

Emails Done Right

Samar Owais, founder of Emails Done Right, shares that her anxiety stems from unscheduled sends and sending emails to subscribers still in the welcome sequence:

“My anxiety peaks anytime I’m sending out an unscheduled email. I HATE sending out an email immediately after it’s finalized. Part of my process is to “sleep” on my emails. It isn’t until I see them with fresh eyes that I pick up things that I would have otherwise missed.

The other thing that makes me anxious is sending emails to folks who’re still in the welcome sequence — that’s the worst email offense I can make as an email marketer.”

The worst outcome for her is not hitting her baseline numbers:

“I’m a little spoiled as an email marketer who’s had some incredible wins in my career. So I say this from a place of privilege — my worst outcome is not hitting my baseline numbers. Whenever I’m planning a campaign, I decide on three sets of metric numbers: baseline or good enough, as expected, beyond our expectations. The baseline numbers are the minimum I want my emails to achieve, and if I don’t get those? I want to audit and diagnose why, and then optimize until I’m satisfied with the result.

You’d be shocked at how often that happened early in my career. But figuring out why an email didn’t perform and then optimizing it is what made me a great SaaS email strategist.”

Samar built a five-part checklist that she couldn’t survive without:

“I wouldn’t survive without my Email Conversion Checklist. It’s got 5 parts: prep work, strategy, getting our emails opened, read, and clicked.

• Step 1 (prep work) is all about internal decision making.
• Step 2 (strategy) is all about figuring out our macro and micro conversions and our backup plan for folks who don’t convert.
• Steps 3, 4, and 5 focus on different components of the email and are more tactical.”

She also reminds us that making mistakes is part of growing into a better email marketer:

“Do your due diligence then put your big girl or boy pants on and hit send. And if you mess up? It’ll make you a better email marketer. You’ll be in good company. Every seasoned email strategist’s QA checklist or process is built on the mistakes they made. Those processes and checklists are battle-tested for a reason. So take a deep breath and hit send. Good luck!”

Emailmonday

Emailmonday founder and email marketing consultant Jordie van Rijn says early in his career, he was overthinking what other people would say about his newsletters:

“Your very first send is super exciting and you may feel anxious. But with practice and experience, and higher email frequency, it becomes more routine. Like a muscle — you train it, it becomes easier. At least for me.

There was a time where I would be thrilled but at the same time pretty nervous about what people would think about my newsletter. Not for the brands that we sent mail for while working at a marketing agency — mainly for my own newsletter.

Other people who are specialists in their field may recognize this. What would people think? Is it good enough? Is it providing enough value? Because… well… you imagine everyone being critical and going through your words with a fine-tooth comb. And as an email marketing specialist that feels doubly true. Both the content AND the email. It should be up to some ‘expert standard’ we make up for ourselves.

The truth is: you are probably the one who cares the most about your own writing and emails. Done is much better than perfect. And no true expert will look down on someone who is obviously putting in the work. And if they care enough to give feedback — positive or critical — that’s already a big win.”

Jordie made an 11-category pre-flight checklist not only to catch mistakes but to make sure that his emails are clear, action-oriented, and valuable:

“When I first made my pre-flight checklist, it wasn’t just to catch mistakes but also to check: is my email very clear, is it action-oriented, does it provide value to the reader as well?

What helps is to know your numbers by heart. Know exactly how many people are in your database and what you’d expect your selections to be, and even the results in opens, clicks, etc. Have those top of mind — this will prevent, in part, you picking the wrong selection or list by accident.

To avoid mistakes, here are some important tips:

1. Don’t write your emails in the email marketing software directly. Rather write/create it outside of it and then load it in.
2. Minimize feedback rounds and what people can give feedback on. Set expectations clearly. If someone is over the deadline, send without their feedback.
3. Use an email master template, so you don’t have to worry about the coding, brand, and technical things working well.
4. Know your numbers and your database inside out.
5. Always, always schedule your emails to go out later — preferably the next day. The most common small mistakes happen when you just did a test send, corrected something, then did another change under time pressure. Scheduling for the next day prevents that.”

He advises fellow email marketers to take comfort in the fact that nobody really knows for sure if an email will have the expected results:

“If you’re anxious about whether you are doing it right and if the email will have the expected results, then take comfort that nobody really knows for sure. And we are all learning. Some of my own thoughts on that made it all the way into the email marketing quotes hall of fame: ‘Design like you are absolutely right, then optimize like you were wrong from the start.’

And to add one for when working with colleagues and customers: ‘If we all have an opinion about how it should be done, let’s just go with mine. Seeing it’s my job.’ It may just get a laugh — and usually that’s all it takes.”

CaaSocio

Aiza Coronado, co-founder of CaaSocio, says that her anxiety is tied to time zones, audience control, and deliverability signals:

“It actually depends on the type of campaign I’m sending. If it’s a sales campaign, my anxiety is around whether I scheduled it correctly (hello timezones). I’m paranoid because even a small miss can affect performance.

For newer flows, even if I’ve tested the actual attributes and filters, I still feel a bit paranoid about sending it to the wrong segment altogether. That’s actually why I don’t like sending flows to segments—especially in Klaviyo. I’d rather put filters that way, I have time to check the users who are about to go into the flow and whether the conditions are functioning properly.

And for deliverability-focused clients, it’s a different kind of anxiety. I’m watching the opens immediately. I hit refresh hard! The open rate after the first 5 minutes is a critical signal that tells me if inbox placement is holding. So my email anxiety isn’t random—it’s tied to timing accuracy, audience control, and deliverability signals.”

She shares that the worst case scenario for her is sending the emails to the wrong segment when there are changes such as onboarding logic shifts:

“The worst outcome I imagine is sending the wrong message to the wrong user, especially in SaaS onboarding flows where everything is behavior-based and highly intentional. For example, we send different emails depending on whether a user has added their credit card or not. So if a paying or active user suddenly gets an email saying, ‘You haven’t added your credit card yet…’ or the ‘Your trial is ending’ email goes to someone who’s already converted, that creates confusion immediately. And it’s not just a small mistake, it breaks trust. That’s one of the horrible scenarios I imagine, and it would happen once or twice in real life usually during moments of change. Like when onboarding logic shifts (e.g., removing credit card requirements), even with preparation, edge cases slip through.

But here’s what I’ve learned: most mistakes don’t go to everyone, they go to a small subset. Monitor closely (especially in the first 24 hours), you can catch and contain mistakes fast. And most importantly: speed of correction matters more than perfection.”

She has separate pre-send processes for email campaigns and workflows:

“I have a very consistent pre-send process, and it’s a mix of technical checks and controlled paranoia.

For campaigns: I always send a test email to myself and/or my team, review it on both desktop and mobile, check the content/layout/formatting, click every single link, and double- to triple-check the recipient segment.

For flows, it’s more layered: I follow a segmentation framework where users should only qualify for one flow at a time (to avoid overlapping emails). Before going live, I review entry conditions, filters, and overall flow logic. And once the flow is live, I monitor users who are queued to receive emails and manually check their profiles to confirm they actually belong in that flow. Even after triple-checking everything, I still verify in real-time. It might sound paranoid, but for me, that’s what creates confidence.”

Aiza also reminds us that mistakes can happen, and what’s important is to fix it fast and learn from it:

“No matter how experienced you are, mistakes can still happen. I mean, we’ve all gotten those empty test emails from HBO, right? But that doesn’t mean we get careless.

My operating principle: get it right the first time as much as possible. But if something breaks — fix it fast, learn from it, and move on. And most importantly — don’t let one wrong send define your entire email career. Keep on sending.”

Don’t let the anxiety get in the way of sending more emails

Mistakes happen, but that shouldn’t stop you from sending emails. These unfortunate mishaps teach you valuable lessons and help you grow into a better email marketer.

Because waiting until everything feels perfect isn’t realistic. There will always be one more thing to check, one more way it could go wrong. At some point, you just have to decide when that email or workflow is good enough.

So take a deep breath, run through your pre-send checklist, and hit “schedule for later”.