How to gain confidence in selling as a solopreneur

Happy Monday folks, back with another update.

I had an interesting email exchange after one of my updates from last week talking about the outrageous prices at sports events, movie theatres, etc.

Are you struggling with sales for your solopreneur business? Maybe you can relate to the below:

“I’d say it’s a lack of confidence in selling. As I have full confidence in the products. Lack of experience also. A feeling of not wanting to be pushy. So knowing how to sell without pushing.”

This is a very common feeling and struggle for solopreneurs, and I remember feeling it myself.

There’s lots to be talked about when it comes to solopreneur sales, but I’ll keep my thoughts to two main ones for the purposes of this topic.

First, like anything, improving in sales comes with practice.

Believe it or not, you will get better and become more confident in yourself when you just get more reps in. For anything.

Learning to ride a bike? Get on the bike.

Want to be a better writer? Go write stuff consistently.

Trying to improve your sales skills? Go try to sell more stuff!

There’s obviously more to it than that, but don’t forget – more reps = more mistakes = more lessons learned = improvement = getting better over time = more confidence = more sales.

Don’t ever think that you can’t get better at something the more you do it. You can, so go get more reps in.

And second, I find a lot of problems with sales confidence melt away if you can change your mindset.

At the beginning, most solopreneurs don’t have confidence in what they’re selling for a variety of reasons, and usually feel like selling is slimy and stealing money from people.

It’s not that at all.

You need to think of it like this: there are billions of people all over the world that are facing problems. They are looking for solutions to those problems, something that can actually help improve their lives. But if you never put it in front of them, they’ll never benefit from it, they might never fix that problem, or worse, they might go buy someone else’s crappier solution.

Quick example: imagine you sell homemade, fresh pasta.

You’re working a farmer’s market, and there’s a gentleman walking around the farmer’s market just itching to get something good so he can cook dinner for his family that night.

You happen to be selling something amazing that could satisfy that problem – but you’re too nervous or scared or hesitant to speak up, and he walks right by you.

Instead, around the next corner, some sleaze ball is yelling “homemade pasta for sale!” Little does everyone know that he just buys packaged pasta from the general store, removes the labels and puts his own on top.

The man buys that pasta, after being convinced from the store owner, and it ends up tasting like store-bought crap.

In summary: don’t think of it as selling, think of it as solving peoples problems. And understand that if it’s not really solving a problem for them, they won’t buy from you anyway!

As solopreneurs, it’s our job to show people the products and services we have, to educate them about how they can solve their problem, and then let them make a decision for themselves.

They key to gaining confidence in sales

As I’ve thought more about it, confidence in anything usually comes down to the same thing.

Doing it a lot!

Hot tip: do NOT put sales on a pedalstal and pretend like it’s harder or more intimidating than anything else. It isn’t.

Maybe you’re not the best solopreneur at it, maybe you’re more introverted and don’t enjoy it as much. That’s totally fine.

But do yourself and your business a favor, and don’t pretend like it’s harder than learning almost anything else.

Let’s do a quick activity:

For 30 seconds, think of the things you’re most confident doing. Could be anything: a sport, a game, marketing, blogging, anything.

Think of the top 3 things you’re most confident doing…

Now ask yourself this: how many times have you done those things?

  • If you’re really confident writing blog posts – how many have you written?
  • If you’re a really confident speaker – how many talks have you given?
  • If you’re really confident playing Call of Duty on Xbox360 (or whatever the latest version is…) – how many games have you played?

I bet that your answer is “a lot”.

It has to be. It’s simply how these things work.

Sure, some of us might be better at certain things, and some of us might be more inclined to pick things up quickly. But it doesn’t mean you still can’t get good at it, with more reps.

Let’s bring this back to sales for solopreneurs.

I bet a bunch of you are introverts, and don’t like selling as much as some of your extroverted counterparts. That’s totally normal.

But it doesn’t mean you can’t get really good at selling.

I was one of those people – no sales experience, introverted, hated the idea of “persuading people”, taking their money, going to big events and networking with people.

But you know what happened?

How I started in sales as a solopreneur

Back in 2017, I was a rookie solopreneur trying to get my immigration law firm off the ground.

The only problem was I didn’t have sales experience and had no clients.

It took me months and months to land my first client – I believe it was 5 months to be exact – and then slowly the snowball started rolling from there.

But I’d say it took me a solid 1.5-2 years until I really got decent at selling (decent, not great).

The interesting thing for me was that I didn’t use all that much strategy, but what I do recall is getting way more confident on sales calls when:

  1. I became more of an expert in my field, meaning I could talk about the service I was providing really well and answer any questions anyone had about it, and
  2. I’d had 100+ sales calls under my belt, so I knew what to expect (in most cases)

The world of solopreneur sales can be a big one, a big rabbit hole you can dive into, read books on and study for the rest of your life. You can learn about perfect times to call, opening lines, how to address hurdles and obstacles from your clients, and more.

And that stuff can certainly help – heck, I’ve read my fair share of books on sales.

But for those of you new to sales, especially introverts who hate the idea of it, that can also be intimidating and stop you from really giving it a try.

Sales isn’t about perfect pitches, or well-crafted answers, or big expense accounts for dinner.

It’s about making it clear to people that you have a solution to their problem, and that you’re a good person to work with.

If I could summarize in some quick bullets:

  • always be on time for calls/meetings
  • make yourself presentable and show up with a smile on your face (whether it’s in-person, over Zoom or whatever)
  • be able to talk clearly and efficiently about how you can help
  • talk to as many people as possible so you can get more reps in and gain confidence

That’s it! Can’t be too hard, right?

Give it a try and let me know.

Want to hear about how Lucas started a new business, cold called 400 companies and landed The Pokemon Company as his first client? He talks all about it, and how it also took him some time and dedication, in episode 117 of the SG Podcast – give it a watch or a listen here.

Controlling the sales conversation

Lastly, I had a great email response from a subscriber (make sure to get my updates right to your inbox here):

Can relate, especially about becoming good and knowing how to talk about what you do. The other big thing for me was to learn how to get and keep control of the conversation throughout.


I’m sharing this response for two reasons:

First, because I feel like as solopreneurs, it’s so hard to get a sense for what is “normal”.

You might be going through the pain of starting your first biz right now, and it’s taking months to get your first client. Well, from my story above and this lovely subscribers reply, hopefully it’s clear that it’s VERY common to take 5+ months to get some revenue coming in.

So if you had any doubt, or are feeling down about a few months of struggles, you’re in good company!

Second, he makes a great point about getting and keeping control of a conversation.

And it brings me back to my earlier points about getting more repetitions in. Because when I was first starting out and not so confident, you tend to be more defensive and let the other person lead the way.

But after hundreds of calls and/or years of selling, you get a good sense for the “journey” you want to take your potential client on during a sales call.

For example, it’s usually a good idea to understand them and their business, dig into the pain points a bit, then transition into how you can help, pricing, etc. After a while, it feels natural and if things are veering of course, you might even interrupt potential clients to keep things moving along – something you might not dare doing early on.

Think of it like a dance – you want to be the one taking the lead, staying alongside your partner (prospect) and gently guiding them to the finish line.

It’s something you can certainly try to learn, but also something you can only really get a great sense for after doing it hundreds of times.

Anyway, I won’t beat a dead sales horse, but if you’re struggling or feeling a lack of confidence, get more reps in.

And if you want more tips and stories like this right to your inbo, make sure to join my list here. Have a great weekend and keep grinding.

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