Let’s get straight to the point.
What’s the key to success in freelance writing?
Following up.
Most freelancers probably have a list of contacts and send out a few cold emails a week.
But frankly, that’s not enough.
This approach misses a crucial step: sending email follow-ups.
Just sending one email isn’t going to get you much progress. Most people aren’t ready to buy right away. It’s the later emails where you start making real progress.
Keep reading to learn more, or check out the video:
The Reality of Cold Emailing
Doing outreach right means sending personalized cold emails consistently, aiming to build personal connections and get new clients.
Yet, there’s a common mistake even the most diligent freelancers make: ignoring the follow-up.
Most people send one email, hear nothing, and give up. But the majority of responses come from follow-ups, not the first email.
Here’s what the data shows:
- 70% of cold emails never get a follow-up at all
- 48% of people never even make a single follow-up attempt
- Only 2% of responses happen on the first contact
- 55% of replies come from a follow-up email, not the first one
- 80% of deals require 5 or more follow-ups
If you only send one email and move on, you’re leaving clients on the table.
Why Follow-Ups Work
When you reach out via cold email, the odds of your prospect needing a freelance writer with your skill set at that exact moment are slim.
A potential client may not be ready to hire a freelance writer now. It can be a completely different story in 3, 6, or 9 months down the road.
The goal of the first email isn’t to land a client immediately. It’s about staying relevant and top of mind when the need arises, which may be months or even years down the road.
Timing Your Follow-Ups
Don’t follow up the next day. Wait 2-5 days between the first and second emails. Too soon feels pushy, too long and they’ve forgotten you.
After that, set up a timing cadence. These are guidelines; figure out what works best for you. After your initial follow-up:
- Send the next follow-up a week later.
- Then, wait two weeks before the next one.
- Follow with a month’s gap.
- Extend to quarterly.
This schedule ensures you check in regularly but not so frequently that it becomes annoying. It also helps give enough time so that things may change. You want to balance staying top of mind and lucking into a moment where they need your services, and being respectful.
Offering to help is not annoying; spamming is. And if they tell you to stop emailing them, take their email off your follow-up list.
I have some clients I send quarterly follow-ups to that line up with the calendar and give you a good talking point. For example, either right before the holiday season, saying I can help them get any last-minute requests done before the end of the year, or mid-January, wishing them a Happy New Year and seeing what they have coming up. Then I’ll send another in the spring, another in the summer, and another in the fall.
Personalization is Everything
I’m not gonna lie to you. I get so many crappy emails.
They’re not personalized. Perhaps they were written by AI, and then you get follow-ups every day that are also not personalized, and it drives me crazy. Those people give a bad rap to the people who do it properly. Everyone hates getting cold emails, and those people are why.
If I get an email where I see someone has taken the time to learn about me and the site, I’m way more likely to respond.
That doesn’t mean you have to spend hours personalizing. Just customize the first sentence. That’s honestly all you need.
So many people send out bad, generic emails that even a tiny bit of effort helps you rise to the top.
And close it with my secret weapon, the easy out.
This approach is non-intrusive and keeps the door open for future communication.
Staying on the Radar Without Being Overbearing
In most cases, when you’re following up, you’re actually doing the other person a favor.
If I’m at a point where what they’re offering isn’t something I need, I’ll ignore it. I get too many emails to respond to every single one.
But if that person follows up on a regular basis, there’s a good chance I’ll be interested somewhere down the line. And rather than having to go out and find someone for what I need, I’m way more likely to connect with the person in my inbox sending me thoughtful emails.
Different Ways to Track Follow-Ups
There are a couple of ways to go about this, and there’s no right or wrong answer. It’s what works for you.
Some people prefer to just use a manual spreadsheet and track it that way. That works fine.
But I think there are tools that work a lot better.
Streak for Gmail is a solid option. It essentially turns your Gmail inbox into a CRM, and it’s free to use. You can track when you send emails, see if they’ve been opened, and add notes to remind you when to follow up later. If you set up a cadence, you can get reminders when it’s time to send the next email.
AI tools like Claude or ChatGPT can also help if you hate spreadsheets. I keep Claude updated on the date, what outreach I did, and who I contacted. It tracks everything for me. Then I can go back and ask for weekly or monthly updates to see my progress, like how many cold emails I had to send to land calls, and then clients.
It’s like having a marketing assistant who never forgets anything.
Whatever system you use, the point is to have one. Once you have a way to track your outreach, it’s so much easier to send follow-ups and actually stick with it.
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Don’t Ignore Email Follow-Ups!
The whole point of this post was just to say follow up.
You’ve done all the hard work building your portfolio and writing samples. You’ve got a lead, researched the person, and spent time crafting a thoughtful email.
Don’t let all that effort go to waste. Spend the extra few minutes to write a follow-up and create a schedule to send more.
That’s going to give you the best shot to get on that person’s radar and hopefully land the gig.
Sean Ogle
Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.Join over 40,000 people who have taken our 6 part freelance writing course. Sign up below and let’s do this together.
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