What's Your Selling Roadblock?

So as of recording this I am just wrapping up the biggest and most successful launch I’ve ever done in my business of my new program, Your Simple & Spacious Business, and I’m starting to reflect on what I’ve learned from this launch and how I can take those lessons with me moving forward.

I don’t think that selling comes easy to most of us in business, it’s scary to take up space and to open ourselves up to rejection and to be brave enough to put our lights on in our work and welcome people into our offerings and to buy from us.

For me the biggest roadblock I’ve been working through over the past year or so is figuring out how to sell 1:many offerings as I’ve mostly had a very client based business over the past 8 years with some smaller 1:many offers weaved in as secondary income.

Selling my 1:1 offers does feel as close to easeful as possible for me now, I’ve been booked up for 8 years at this point and I’ve built my business to a place where I can just put my lights on and let people know that I’m booking and then the right people for that season get in touch and book their spot. And I’ve made that sound really simple, and in many ways it is but it’s built on the foundation of years of sowing seeds through my free content and my word of mouth and testimonials which has then made booking up my client schedule a simple process for me.

But with my 1:many offers like programs and courses and digital products I’ve found that it’s really quite a different ballgame and what I’ve learned is that I can’t sell 1:many offers in the same way I sell 1:1 and so I’ve really had to go on a journey of figuring out my approach to selling group programs that embodies the gentle and human way I’ve always sold my 1:1 offers but while also embracing the fact that I need to put my lights on more to sell group offers too.

I’ll talk about more of these lessons in an upcoming episode soon I’m sure but today I want to dig into the selling roadblocks I see and support my clients through in the hopes it may be of support to you in this season of your business too.

The first roadblock is not wanting to annoy people.

So many of my clients tell me they’re afraid to sell because they don’t want to irritate people or take up too much space or people unfollow them or unsubscribe from their newsletter and I get it as I’ve navigated all of these fears too but the most helpful thing to remember here is that when you run a business the people paying attention actually expect you to sell to them, they are interested in your work and are following along so that they can keep up to date with what you do. They may not always buy from you but they are in your orbit because they’re interested in what you do.

So the people who unsubscribe or unfollow you just aren’t aligned potential customers for you right now and that’s okay - when you’re obsessing over the unfollows and unsubscribes remember to refocus on the people who haven’t, that number will almost always be bigger and that’s a reminder that it’s okay for people to leave when you’re not the right fit as so many people are and are continuing to engage with your work.

It’s our job in our business to sell but we’re also allowed to do this in a way that feels aligned with our values and our energy but the only way to do that is to let go of the fear that we’re annoying people when we take up space with our business and instead reframe it as we’re actually making it easy for the people who will find joy and value and support in our offerings and products to actually know they’re available for them.

The mindset shift I’ve found the most supportive over the years is that I’m inviting not selling, I’m not here to persuade or convince someone to buy from me, I’m just making it easy for my hell yes people to know that what I offer is a hell yes for them when the time is right for them.

The second roadblock is that you’re afraid people won’t buy.

I think that a slow launch or zero sales is a rite of passage as a business owner. I remember a few years ago I decided to experiment with hosting in-person small workshops at my home. The first sold out in under 2 hours so I decided to launch more and put two up for sale on the same day and… it was crickets. Only one spot sold and I had to refund it. I think in some ways it was divine intervention from the universe as during the date for the first workshop that didn’t sell I actually was undergoing the IVF cycle that conceived my son and the second date was then during the early stages of the pandemic so neither of workshops could actually have gone ahead in the end but still I remember thinking oh, what have I done wrong why did the first sell so easily and the second two just didn’t?

And the truth is, sometimes things just don’t sell well or we have a slow season and we can learn from it and tweak things moving forward but if we let the fear of things not selling hold us back then we’d never actually sell at all.

The worst thing we can do for our business is stand on the sidelines waiting for certainty before we take action. And that doesn’t mean we should just charge ahead without intention, instead it means we should get clear on what we’re going to do to sell as strongly as we can but also be okay with knowing that it’s an experiment too. If you’d love to see an example of planning with intention for a launch you can dive into my Launch Your Damn Offering video series where I walk you through the behind the scenes of planning my launch for Your Simple & Spacious Business.

The third roadblock is that you don’t want to be sleazy.

And listen, I get it - I don’t want to be sleazy either. I hate feeling like someone is aggressively selling to me and trying to manipulate me into hitting that buy button. I have zero interest in doing that in my business.

I want to sell in a gentle, human, respectful way, in a way that empowers my clients and customers to only say hell yes to diving deeper together when the time is right for them. And here’s the good news: I’m proof that this is possible. Like I said, I’ve been booked out for eight years now with 1:1 clients and I’ve done that by sharing content, building an email list, and putting my lights on a few times a year to say I’m booking - no sleazy sales tactics in sight. And same with my 1:many offerings, I think I launched my first online course back in 2016 and now with Your Simple & Spacious Business being I think my 12th or 13th 1:many offer at this point and I’ve never felt like I’ve had to sell in a way that feels out of alignment with my values in my business.

I think that sleazy selling comes from a place of insecurity, it comes from a place of thinking we have to convince someone to buy from us. Instead I think a whole lot of magic happens when we create offers and products that we believe in, that we’re passionate about, and when we create invitations to those offers that feel human and fun and clear and that also recognise that our clients and customers know when the time is right for them too.

If this is the roadblock you really get stuck with my encouragement is to find examples of people selling in a way that really resonates with you, let it illuminate for you what’s possible and model ways of selling that feels aligned for you.

The fourth roadblock I see some of my clients struggle with is that they’re afraid that they don’t actually know how to sell.

Marketing and selling can feel so complicated in business, especially as we’re bombarded with everyone else’s strategies and formulas and approaches and it can feel like it’s this whole foreign language that we have to learn in our work.

If marketing is something that feels alien to you I’d really encourage going back and listening to last week’s episode where I break down three steps to simplify your customer journey, this will help you visualise a really simple approach to your marketing plan and how to make it easy for your hell yes people to discover your work and say yes to diving deeper into your offerings and products too.

And most of all remember that selling is a muscle we build and develop in our business - and we’re always learning and evolving and growing along the way. You are capable of developing your own approach to selling in your business in a way that feels aligned for you and supports your business to thrive - you’re probably going to have to experiment quite a bit and be willing to risk failure but that’s ultimately what our businesses ask of us.

Because anyone who is running a thriving business has had a slow launch, has had a zero sales launch, has had quiet periods, has had disappointment and knock backs and has chosen to keep on showing up and figuring it out as they go.

Selling is an essential skill in our business but it doesn’t have to be sleazy and overwhelming, it can be simple and human and even fun too.

So my encouragement to you today is to find and embrace an approach to selling in your business that feels good to you, to know that this is one never-ending experiment and that one bad month or quarter or launch doesn’t define you and your business, and that you’re not alone in finding this hard sometimes too.

Bear witness to your roadblocks, gently find a way around and through them, and discover on the other side a version of you who sells with trust and ease and a business that can truly thrive when you’re steering the ship with courage and intention and focus every step of the way.


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Jen Carrington