Content Therapy is Managing Editor’s twice-monthly advice column, where Paul Chaney responds to your questions about the messy dilemmas content marketers face in their work. We are (obviously) not licensed therapists. Email us your questions at

Will I Anger My Boss if I Take on Freelance Work?

Dear Content Therapist: I’ve been a full-time content marketer for the past few years, and I’m enjoying my role and the company. But I was a longtime freelancer before taking this gig, and I’ve recently been approached about doing some side work. These offers are enticing, both for the extra money and as a chance to explore other interests. But I’m not sure what my employer would think. I know enough to turn down work that’s in direct competition with my full-time job, but the rest feels murky. We don’t have a written policy about outside work, and I’m pretty sure some of my co-workers have side hustles. Should I ask my manager for permission to freelance or only when I’m worried about a conflict of interest?  — THE FULL-TIME FREELANCER

Paul Chaney: Your question is one to which I can relate. I freelanced for several years while working full-time. I did not disclose that information precisely for the reason you mentioned: There was no written policy forbidding it. However, don’t take my actions as a license to follow suit. 

You know the adage: It’s better to ask forgiveness than permission. But is it? Better to ask forgiveness, that is. You assume some measure of risk either way. 

Doubtless, you could justify taking on side work given that there is no written policy against it and your certainty regarding co-workers doing the same, then apologize later if it presented a problem with your manager.

You could also speak to your manager as a sign of respect, letting them know you’ve been approached about doing some freelance work, with the reassurance that you won’t take on work that represents a conflict of interest. 

That could conceivably result in one of two responses: appreciation for being forthright or raised suspicions that your reason means you’re looking for another job. However, not telling your manager and being found out could also jeopardize your career. 

Which begs the question: What’s the trust level between you and your manager? If it’s substantial, there’s every reason to believe they won’t view this negatively but congratulate you on the opportunity.

If you’re unsure, however, you could approach the conversion as seeking guidance rather than asking for permission. Tell them you value their opinion and want to ensure you’re making decisions in the best interest of you and the company. Also, understand that it is entirely within their right to expect your full-time job to be your priority in exchange for your salary.  

Ultimately, it may come down to how much risk you want to accept. That’s a judgment call you have to make.

Help! We’re Not on the Same Page as Our Clients!

Dear Content Therapist: My team’s been running into problems where we’re delivering content that doesn’t meet the client’s expectations. But I don’t think the core issue is my team’s competence. We have a smart, hardworking team of content creators. My concern is that we’re confused about what we’re supposed to be delivering. Somehow, we’re not aligned on expectations at the start of the project, or maybe the client is changing their mind. I’ve encouraged my team to ask more questions, but I don’t want us to sound like we don’t know what we’re talking about. How can I help my content marketing team align with clients without losing face?  — OUT-OF-ALIGNMENT MARKETER

Paul Chaney: Your concern over losing face should be over the possibility of losing a client. Setting expectations from the outset is always the best practice for any client relationship. If that wasn’t the case here, you created a problem for yourself. However, it’s not one that you can’t resolve by putting some communication guidelines in place. 

Here’s what I would do in this situation:

Meet With the Client to Clarify Expectations

That doesn’t necessarily mean asking more questions; rather, it’s ensuring you fully align with their expectations. 

Share your understanding of the expectations. If they agree, follow the steps listed below. However, if they object, you’ll need to ask what they want changed to align everything. You may also have to take one for the team and apologize for any misunderstanding. Either way, thank the client for clearing things up. 

Take Action Internally

In hopes that everyone is satisfied that you have a mutual understanding, take the following actions:

  • Schedule regular client meetings. Check in at different project intervals to inform them of your progress and ensure continued alignment. It’s much easier to make minor course corrections along the way than significant changes at the end. They’ll likely appreciate being apprised of your activities. 
  • Seek feedback. Encourage your team to actively seek feedback. This isn’t a sign of incompetence but instead of professionalism. It shows the client you’re committed to delivering the best content possible. Remind them that it is a collaborative process.
  • Document changes. Document any changes or additional requests from the client. This step safeguards your team and serves as a reference point when questions arise about the project’s scope or direction. 
  • Stay informed. Meet with your team regularly to ensure everything stays on track. Answer their questions, and clear up any confusion. 

Going forward, ask any new client to complete a detailed content brief that includes their objectives, target audience, preferred tone, style, key messages and other specific requirements. That way, you won’t repeat the same mistake.. 

Disclaimer: The advice offered in this column is intended for informational purposes only. It is not intended to substitute for advice from a licensed mental health provider, health care provider or legal professional.

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