3 mindset shifts that made following up easier

How to follow up with potential clients without feeling awkward or pushy.

Photo by Compagnons on Unsplash

If you’re reading this post, you probably already know you should be following up with potential clients. But most freelancers don’t do it often or with much consistency. So where’s the disconnect?

I’m guessing it’s probably some combination of the following reasons:

• They don’t want to bother people.

• It feels uncomfortable when someone doesn’t respond.

• They assume silence means no.

• They worry about looking desperate.

Because of this, I’ve noticed that most freelancers are constantly winging it when it comes to following up, so the results are minimal and inconsistent. To help you break free of this pattern, here are three mindset shifts I’ve had when it comes to follow-ups.

1. You need a follow-up routine

Years ago, I decided I wanted to start working out regularly. My goal was to work out five days a week, so I decided I would do it on Monday, Tuesday, Wednesday, Friday, and Saturday. But inevitably, there would be a Monday or a Tuesday when I just wouldn’t feel like working out. No big deal, I would tell myself. I’ll just skip today and do it on Thursday instead.

Do you think I made that workout up on Thursday? Um, no, I did not. Those were typically the weeks I only worked out two days, or just blew it off altogether. Over time, I realized that if I wanted to be consistent with working out, I needed to have a specific plan and I needed to stick to it.

And honestly, following up is no different. When you first cold email a prospect, do you know how long you’ll wait before following up with them? If not, there’s a good chance you won’t do it.

Personally, I always follow up on Thursdays. I don’t send cold emails or write social media posts, I just follow up with prospects or clients I haven’t heard from in a while.

After sending that first cold email, I typically wait a week and then send a follow-up email. If I still don’t hear back, I’ll send another quick email two weeks later. If I still don’t get a response, I might reach out to someone different within the company. You don’t have to copy my process for following up, but you should come up with your own.

2. My goal isn’t a yes — it’s to get a response

Okay, let’s state the obvious first. When I cold email someone, my preferred response is a yes. But when I follow up with someone, my ultimate goal is just to get a response. Because once someone responds, I know what to do next.

If they say yes, then great — we can talk about assignments or next steps. If they say no, that’s helpful too. It tells me that I should focus my attention elsewhere instead of continuing to wonder if that company might hire me.

The hardest situation is when you’re stuck in that in-between stage where you don’t know if the person is interested, too busy to respond, or simply not seeing your emails. And that uncertainty can drag on for months if you let it.

I’ll give you a real-life example of this. I had been writing articles for a fintech company for about five years when my main point of contact left the company last fall. Before he left, he mentioned that he would connect me with the person who would be taking over content, but that handoff never happened.

So I realized it was up to me to find this information. I managed to track them down on LinkedIn, so I sent a quick email introducing myself and asking if they needed any articles that month.

My inbox was a bit of a ghost town for the next couple of months as that person never answered a single email I sent them. After about three emails, I tracked down someone else at the company and reached out. Finally, in February, I received a response from the Director of Marketing explaining that they had decided they no longer needed freelance writing support.

Some freelancers might see that outcome as a failure, but I actually consider it a win because now I know exactly where things stand. Instead of wondering whether work might pick back up, I have a clear answer. And that means I can move on and focus my attention elsewhere while finding other ways to stay in touch.

3. A no today doesn’t mean no forever

One of the biggest mindset shifts I’ve had about freelancing is realizing that client relationships rarely have an obvious beginning and end. And one pattern I’ve seen in my own business is that once a client has paid me over $5,000, there’s a good chance that they’ll stick around for years. To give an example of this, my longest client has been with me since 2019!

But even if the relationship does eventually slow down or stop, it’s not uncommon for those same clients to come back at some point. Things change, content strategies shift, and opportunities have a way of resurfacing. That’s why I try not to mentally close the book on a client relationship.

The same thing can happen with cold outreach. I’ve had multiple situations where someone told me they didn’t need freelance writers at the time, only to reach out months later when their workload suddenly increased. Content needs can change very quickly inside a company. One quarter they’re fully staffed, and the next quarter they’re scrambling to find help.

Now, if someone clearly states that they don’t need freelance help, I don’t keep pestering them with emails asking for work. But I do look for ways to stay in touch with that person and remain top of mind. That could look like commenting on their LinkedIn posts or sending a quick check-in message once or twice a year.

Because in freelancing, you never really know when a past conversation or client might turn into a future opportunity. And when that happens, it’s a lot easier to restart a relationship that already exists than it is to build a brand-new one from scratch.

The bottom line

Following up will probably never feel completely comfortable. There’s always going to be a small part of you that wonders if you’re bothering someone or when you should just move on. But following up is a crucial aspect of building a sustainable freelancing business.

And over the years, I’ve realized that following up is really about reducing uncertainty in your business. You stay visible to the people who might hire you and keep relationships alive that could turn into work months or even years down the road.