Every success guru and entrepreneur will probably tell you advice along these lines: You have to create areas of opportunities for yourself.

Rather than sit back passively and wait for things to happen, you have to make them happen for yourself. The same then is true for anyone running their own business, especially for freelancers.

Last month, I sent my very first cold pitch in months… and I got a response in 5 minutes.

I was surprised for several reasons, but mainly because of how easy it was. After putting off new pitches for months, I received a response in a matter of minutes. It reminded me of the power we have in creating opportunities for ourselves.

It inspired me to create an experiment. I dedicated an entire week to cold pitching myself and my services for various opportunities I was interested in — from writing for publications I admired to joining podcasts I looked up to. I wanted to see what would unfold if I dedicated more time to cold pitching and how it would impact my approach to building my business.

Here’s what I learned.

My cold pitching experiment

2023 was the first full year of running my business. I focused on building systems, creating sustainable income — and, most importantly, staying sane and grounded while learning it all as I go. For the record, I think that is a huge accomplishment in itself.

However, as I reflected on the past year and what I wanted to accomplish this year I realized one trend that I wanted to focus on: being more intentional about my time and the projects I’m working on. It’s not enough to run a business on autopilot, I want to be an active participant in creating a career and a life that I love.

While I had been incredibly driven in the beginning of my entrepreneurial journey about what I wanted to accomplish, the reality is that it changed over time. I started to accept work that would come to me and lose foresight around my larger vision.

In short: I got lazy and complacent.

Building a clear vision

I realized that I needed a stronger understanding of where I wanted my business and my career to be heading. Here’s what that looked like for me:

• What clients I’m working with

• What projects I’m working on

• What topics I’m writing about

• What publications I’m writing for

Rather than trying to re-position myself to attract new opportunities, I knew I had to actively create a plan them.

Enter: the dreaded cold pitch.

I drafted up a quick bio, a description of my services, and links to my previous work. The hardest part is creating a master of list of who and where to cold pitch. I created a range of opportunities that were interesting to me, of dream companies and clients I’d love to work with someday.

Here’s a glimpse into what I prioritized:

My actions

• Pitch to 2 magazines

• Reach out to people I want to work with or learn from

• Find one potential client and cold pitch

• Find peer who’s doing the work I want to do and collaborate

• Pitch book review

• Sign up to be a guest on a podcast

• Publish one article on Medium and submit to publications

The results

• Landed intro call for new client (a large financial publication!)

• Editor responded to magazine pitch. No assignment now but now have an established contact to pitch in the future. This has also inspired to try even more pitches for other publications.

• Booked some coffee chats with peers doing interesting work and found one that potentially has work for me.

• Booked an interview for an entrepreneurial podcast

• Continuing to submit to Medium publications. I’m slowly learning the platform and how to optimize content.

• I became motivated more than ever to keep putting myself out there and seek new opportunities.

Here are the lessons I’ve learned on cold pitching

1. There is always room to pitch more (see my thoughts on abundance mindset)

I thought that once you reached the ‘established’ portion of your career, you were set. The right people and opportunities would come your way. The dream leads would fall right into your email inbox.

While I believe in the power of branding yourself strategically so that the right people discover your services, I still strongly believe that you must keep putting yourself out there time and time again.

It’s important to always make room to attract new leads and stoke these relationships even if it doesn’t go anywhere.

2. Do the thing you’re putting off

I’ve been thinking I needed to add new leads to my roster for a while.

I realized that the mental hurdle around cold pitching was the biggest thing holding me back. Once I did it once, I noticed a few things: it’s not that hard, nor time consuming, and it doesn’t hurt that bad to get rejected or not get a response.

Getting a response to one of my pitches was such a quick and easy win (even if I didn’t get work now for it.)

What I realized is that response to a cold pitch, no matter whether it was successful or not, fueled me to try even more cold pitching attempts.

One magazine pitch turned into four.

When you realize that rejection or no response is literally the worst that can happen, you think why shouldn’t you constantly pitch yourself. If it’s a numbers game, you’re bound to succeed the more times you put yourself out there.

3. Organize leads and ideal clients by A, B, and C tiers

I pitched my ghostwriting services to a venture capitalist that I really admire. She’s a leader in the space and also creates content around being a female in VC and her approach to investing, business, life and more. Prime example of an A-tier client.

I was having a conversation with a friend about this pitch and she gave me the incredible advice: It’s great to go for the A-tier, but you should also focus on your B and C-tiers and work your way up.

Maybe you’re writing for industry blogs or regional publications but dream of writing for The New York Times or even publishing your own book. I’m staying focused on doing great work for clients while keeping big goals in close view.

Stay steady on your work for your B and C tiers but keep your eyes on your A-level goals.

4. Keep dedicated time for cold pitching and building leads

Maintaining a routine for cold pitching keeps you focused on your biggest-priority goals. And can actually make them a reality.

It’s a misnomer to think that only beginners and inexperienced professionals should cold pitch. Of course, as you build a reputation there will be clients and organizations that approach you first. But there is always room, still, to find your dream project or client.

Even during “boom time,” you want to have potential clients waiting in the wings.

But of course life gets busy and you likely get comfortable with the work you’re doing now. It’s easy to let your long term vision fall to the wayside while you carry out your day-to-day. How can you combat this and stay intentional?

Here are my tips for cold pitching:

• Create a consistent time each day, week, and month to cold pitch

• Make a list of your dream clients on companies to work with — of dream projects you’d like to work on

• Track your cold pitches as you do them. Even if they aren’t successful, you’ll find motivation by trying consistently over time.

P.S. This article was first published on my Medium site — you can read more and subscribe here.

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  • P.S. here are my 5 tips for beginning freelancers

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