Freelancing and Love; My Train Ride Taught Me to Pitch Like a Pro?

For the last 12 weeks, I’ve been on the same train from Weligama to Bambalapitiya, and every time, there she is. Let’s call her 'Zara'. She gets on the train at Balapitiya, and I always hope to see her. She's beautiful and calm, and there's something about her that just gets to me. But I haven’t said a word to her. Why? Because I’m terrified! She’s a Muslim girl, and for some reason, that makes me even more nervous to say anything.

This crush has been driving me crazy. But then, it hit me—trying to talk to Zara is just like pitching clients as a freelancer. Seriously, bear with me. It’s all about putting yourself out there, risking rejection, and hoping for a chance. Whether it’s pitching a business or confessing your feelings to someone, the process is the same.

?

Step 1: The Train Ride - Observing Your Target

Every time I get on the train and see Zara get on at Balapitiya, I tell myself, “Today’s the day.” But then, I freeze. I sit in my seat, looking at her from a distance, and think, “What if she rejects me?” It's the same fear that pops into my head when I want to pitch a client. You’ve done your research, you know the client could benefit from your work, but that fear of rejection stops you from speaking up.

But here’s the truth: if you never speak up, nothing will ever happen. I could ride this train for another 12 weeks and never say a word to Zara. Just like I could send another 12 emails and never follow up on a single client. In both cases, nothing happens unless you take the first step.

Step 2: Starting the Conversation

Imagine I walk up to Zara on the train and say, “Hi, I’ve been seeing you on this train for weeks, and I just had to say hello.” That’s a good icebreaker, right? It’s simple, honest, and shows interest. The same rule applies when you’re pitching a client.

You don’t need some fancy sales pitch filled with big words. Start with a friendly, direct approach. Something like, “Hey, I’ve been following your business, and I really admire what you’re doing. I believe I can help you with 'this' or 'that'.” Just like talking to Zara, it’s about breaking the ice, being genuine, and showing interest without overcomplicating things.

Step 3: The Fear of Rejection

Let’s be honest, the reason I haven’t talked to Zara yet is simple: I’m afraid of getting rejected. What if she doesn’t like me? What if she thinks it’s weird that I’m talking to her on a train? It’s scary! But then again, isn’t that the same fear we face with clients? We worry that if we pitch, they might say no, or worse, ignore us altogether. But here’s the thing: Rejection is part of life. Whether it’s in love or freelancing, not everyone is going to say yes. But if you don’t try, you’ll never know.

I could sit on that train every week and keep wondering “What if?” or I could just go for it. The same goes for your freelance career. Don’t let the fear of rejection hold you back. Every no gets you closer to a yes.

Step 4: Making It Fun

One thing I’ve realized is that humour can break down barriers. I’ve imagined saying to Zara, “Hey, I’m not a professional at starting conversations on trains, but I’ve been practising this in my head for weeks now, so here goes…” A little joke can lighten the mood and show that you’re human.

In freelancing, this works too. When you’re physically pitching a client, throw in a light-hearted comment or a joke. Maybe say, “I’m not here to give you a boring sales pitch, I just want to show you what I can do to help your business grow.” Being a little funny shows confidence and makes you relatable. It works in love, and it works in business.

Step 5: Following Up

Now, let’s say I finally talk to Zara. Maybe she smiles, maybe she’s interested, or maybe she’s unsure. Either way, I’ll need to follow up. If I see her on the train again next week, I’ll say, “Hey, nice to see you again. How was your week?”

With clients, follow-up is just as important. If they don’t respond to your first pitch, don’t give up! Send a polite follow-up, reminding them of your offer and your interest in working together. Don’t bombard them with messages, but a little persistence goes a long way. Whether you’re asking someone out or asking for business, consistency shows that you’re serious.

Step 6: Closing the Deal

Let’s say everything goes well, and Zara agrees to grab a coffee with me. Success! In the freelancing world, closing the deal with a client feels just as great. Whether it’s getting the contract signed or getting a second date, you’ve put in the effort, and now it’s time to celebrate.

But even if Zara says no, or the client doesn’t sign, there’s a win in knowing that you put yourself out there. You gave it a shot, and now you can move on to the next opportunity with more confidence.

Final Thoughts: Take the First Step

So, whether it’s a girl on a train or a client in a meeting room, the process is surprisingly the same. Don’t wait for the perfect moment, because it might never come. Take a deep breath, walk up, and say what you need to say. Be yourself, add a little humour, and don’t be afraid of rejection. Who knows? You might just land your dream girl—or your dream client.

For me, I’ve now mastered the courage to grow my freelance business, and I’m always using the tricks I mentioned above. Marketers, entrepreneurs, business owners, and anyone looking to build strong connections can apply these steps to improve their pitch, whether in business or life.

After all, if I can pitch a client, maybe I can finally pitch myself to Zara too.

Senith Samaranayake | The Official?