Welcome to Ask An Online Business Coach – my new marketing Q&A column for online business owners.

This is where you can submit anonymous questions and get practical, actionable answers about marketing your online business and attracting and managing your clients.

Have a question? Click here to ask away and it may be featured in an upcoming column.


Dear Kyla,

I'm pivoting from my career in a marketing agency to being a self-employed copywriter, and I'm starting to have serious doubts that becoming completely self-employed a good idea. 

My original idea was to become a copywriter for online business owners. I would learn how they write to their audience, and then I could take over their email newsletter for them or write sales emails during launches. I do this for agency clients already, and the idea of being able to do this every day would be a dream. 

I'm still in my 9-to-5, and I've been open with them about my new business. Now I realize that might not have been a good idea because it's clear that my parents and partner don't understand the industry. 

They're worried. 

Like… very worried. 

They all express concern about who even wants or needs this service, and how I'm going to balance it – especially while managing my anxiety.

They genuinely want to know what I've been up to, but the conversations always circle back to their concern. Since this happens separately with each of them, so I'm having these conversations multiple times a week. 

I feel like the more I talk about it, the less confident I feel about it. Is this a crazy idea? Do people even need this? I appreciate being able to talk with them, so I want to make the process of pivoting less exhausting without shutting them down completely. Help?

– Perplexed Pivoter


It sounds like you're being incredibly patient with your family as you continually have these conversations with them. 

Only, these are less conversations and more what I like to call people “having feelings at you”.

It sounds like they otherwise have good judgment and are a trusted part of your support system, and I'm glad that you have that. But this isn't coming from their best judgment, it's coming from fear. And being on the receiving end of it from multiple people is maddening.

No one knows the stress of considering pivoting your career into being full-time self-employed better than you do. It's a stressful thing. 

But becoming self-employed is stressful. Even if you're talented. Even if you're experienced.

Even if your family isn't low-key weaponizing your anxiety against you or planting seeds of doubt at every turn. (Imma circle back to that, believe me!) 

At best: they love you and are scared. They are jumping straight to “no steady paycheque!!” and are picturing you on the short road to becoming The Little Match Girl. Individually they're being emotionally immature, and are using that as an excuse to process those feelings verbally with you.

At worst: they're implying that it would just be better for you to make them feel better by changing your mind and doing something they're more comfortable with. It's for the best anyway. You're so fragile and anxious!

Even if they're normally wonderful – they way they're relating to your anxiety is both ableist and optional. They are just as capable of responding by asking how they could support you to make this a more seamless transition for you. 

Or by bringing you cake in celebration! 

It sounds like you're fed, employed in a competitive field of your choosing, doing knowledge-based work, and dreaming of your future. As a human, you experience anxiety. It doesn't define you. You aren't letting it limit your life. I hope you see that in yourself.

You are capable of incredible things. You are capable of helping people. Your work is needed. And frankly, as a copywriter, your experience with anxiety puts you deeply in touch with your empathy. As a writer and a service-based business owner, that's a genuine superpower.

The next time that they ask about how your business is going, I encourage you to stop this cycle, politely and firmly.

“It's going well. There are a lot of moving parts, but I'm lucky that I bring so much experience into this. It gives me an incredible head start! I know we've been brainstorming about it together – but what would be most helpful is having you as someone I can confide in, who's here to listen and encourage me. Would that work for you?”

Most people will agree. Then if/when they fall back into old habits and start asking unhelpful questions? 

Then the name of the game is restating the boundary without giving them more to push back on.

Here are scripts that could help out in the moment:

  • “I hear that you're concerned, but I meant it when I said that I don't want to work through potential problems.”
  • “I'm enjoying working on the next steps, but I don't find it helpful to talk about what may or might not happen in the future.”
  • “I'm really focused on the next steps and validating my ideas. I don't walk to talk about hypothetical problems.”
  • “I hear that you're worried, but since this affects me directly, I need to ask you to talk through those feelings with someone else.”
  • “I'm going to file that away for if it comes up.”
  • “I guess anything is possible.”
  • “I don't want to talk about that right now.”

Or you could employ either of my favourite tactics from the fabulous Dear Prudence:

  1. Pretend to be confused, and respond with “What do you mean?” / “Could you explain that?” / “I'm not sure I follow?” repeatedly until they have to say it all out loud, and hear how ridiculous it is.
  2. Look perplexed and reply, “What an odd thing to say.”

Mix and match until they drop it

It will be awkward. Please remember that you aren't making it awkward. They made it awkward. You are just handing the awkward back to them.

Now, for the question you actually asked: 

Do online business owners really need copywriters?

Yes, absolutely!

Your ideal clients are out there, frustrated that they can't find the help they need. Writing newsletters and repurposing content is the stuff of nightmares for literally hundreds of thousands of business owners.

Your mix of life experience, professional experience, personal interest, sense of humor – and so much more – will make you absolutely perfect for a generous slice of them. 

There are only two people whose opinion of your business matters: you and your dream clients.

Everyone else's opinions and commentary – mine included – is static.

Turn the volume on it down as far as possible, use all the tools in your toolkit to stay motivated, and centered, and keep taking action the next thing on your New Business To-Do List.

In a year, your whole life could be different because of it.

Keep going.

What do you think the writer should do? What did you do, if you've struggled with something similar?
Did this remind you of something you would love to have Kyla's take on? Submit your question or dilemma anonymously here