The Lifelong Freelancer — Simon Harper on Finding His Way into Email

Not everyone enters the email industry through a clearly defined path.

Some careers start with intention and planning. Others begin with necessity, curiosity, and a willingness to pivot when the expected route doesn’t work out.

Simon Harper’s, SRH Design journey into email didn’t start in an office or inside a tech company. It started with self-promotion, adaptability, and a gradual gravitation toward the technical depth of the channel.

I asked Simon a series of questions about his path into email, freelancing, and the realities of long-term independent work. Here are his answers — in his own words.

What originally pulled you into the email world, and what kept you here?

Learning to promote myself first, then doing the same for clients.

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Looking back, how has your professional path evolved — and what shaped those transitions?

I guess I've moved deliverability and technical email marketing into focus, so DNS troubleshooting and technical strategy. But also, I'm still within a particular niche of e-commerce. On top of that, I've been developing designs and templates for content and campaign creation, and I guess it just shifts in the market and with my clients. That's about it. Nothing earth-shattering. It's just kind of where I've moved into. I love tech.

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What inspired you to choose freelancing from the start, and what has sustained that choice?

It's a simple answer for me. I was working in a coffee shop, and I had to work in coffee shops after university because I couldn't get a job with my degree, which was in a totally different field. So I pivoted.

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What challenges still show up in your work, even with years of experience behind you?

I guess the biggest challenge is clients themselves, and budgets, and next goals from within teams that the clients use. In-house teams can be the most challenging.

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What parts of freelancing give you the most energy and keep you committed to this path?

It's the freedom, and particularly with my setup and my family situation, it allows me to work around my kids which is so important to me.

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Why this perspective matters

Simon’s answers reflect a reality that’s common in the email world but rarely articulated plainly: careers don’t always begin with access, mentorship, or clear pathways.

They begin with adjustment.

Over time, that adjustment turns into specialization, technical depth, and a way of working that has to support not just professional growth, but real life as well.

This conversation is part of a broader effort to surface those experiences — especially as they relate to access, learning, and long-term sustainability in email careers.

More voices to follow.

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Add Your Voice!

This interview is part of The Email Freelancer Pathways Project, a series documenting the many different paths into email.

Through a short survey, I’m collecting experiences from email professionals to make these career journeys visible — and to help advocate for better access to the tools people are expected to master.

If you work in email in any capacity, your experience matters.

👉 Take the survey here!

📩 Connect with me on LinkedIn or send a message.

With Love from Canmore, Alberta
Annett
Founder, EmailBoutique.io