How to survive a double life as an operator-creator

The best business content creators still have day jobs. Everyone’s got an opinion, but having hands-on experience is what keeps you grounded in reality.

That’s why I’m a big fan of operator-creators.

That’s definitely been my approach. (You can read the full story here if you want: So you want to be a content creator?) Even though my content and advising work is self-sustaining, I keep taking full-time jobs. That’s one of the reasons I’m guessing lovely people like you keep giving me your precious attention by reading stuff I write: because it’s based on what I’ve actually done.

So I’ve got no plans to give either of these sides of my life up. For the most part, they actually make each other better: my day job makes my content much more interesting and relevant and credible. Writing things out forces me to take the stuff floating around in my brain and turn it into frameworks that I can share with other people. And having my own audience is an immediate win for any company where I work - I can help them with product awareness, brand building, talent recruitment, all of that. I’m like a one-woman distribution channel.

But holy gray area.

I’m not trying to hide anything, but it still feels like a double life. You’ve got two identities and sets of obligations to manage at the same time.

So I’ve created some rules for myself to keep me sane.

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Always Be Disclosing

This whole scenario can be very blurry, so my goal is to always be super clear about my commitments and incentives and priorities. I don’t want anyone to be surprised.

With my employer

This conversation is ideally happening before the first day of work.

It’s not as much of an issue for me these days, because the companies I work with see my content creation as part of why they’re hiring me. Now, they’re not trying to stop me from posting - if anything, they want me to post more. But it was such a key part of my early operator-creator juggling act that I still consider it my #1 rule - make sure they know what you’re doing, and what is and isn’t theirs. This direct conversation is also a good time to set boundaries on what they feel comfortable with me sharing or not sharing in my writing.

If you’ve already got something going, do nottttt try to hide it. If you’ve got a newsletter or a booming LinkedIn profile or YouTube channel or whatever, don’t just treat them like some awkward hobby that you hope nobody notices.

And if you’re just getting started, it’s a good idea to be up front about that too: Tell your manager and/or mentors. Spoiler alert: They’ll probably be excited. Every company is trying to figure out employee-generated content and build-in-public, so if you’re wanting to get your voice out there, they’ll probably be fine with it. They might even help you.

Also: Make sure you read your employee agreement. Make sure you know what you’re literally signing up for when it comes to outside work, IP, conflicts of interest, and confidentiality. Since my content existed before any work agreements I’m signing now, I always make sure that it’s extremely clear that all existing partnerships, content, and audiences stay mine AND I’m explicitly allowed to run my side gigs.

With my audience

Oh, hey, that’s you. Just like I want to lay it all out there with my employer, I’ve gotta be completely transparent with you - especially you beautiful paid subscribers, since you’re also kind of employing me, too?

Particularly with the general Internet public, trust is everything. I want every single person who sees my stuff to know 100% what my incentives are and where I’m coming from.

In an ideal world, people would see my content gradually over time and recognize the context. But… yeah, no such luck. People see one post and make assumptions. Even doing the ‘These opinions are mine and not my employer’s’ type language gets ignored. So I just try to go out of my way to mention what my connections and context are.

With my sponsors / creator partners

Yep, the other other boss.

Whenever I’m collabing with another company that is not Lovable, it’s particularly important to me that they know which ‘Elena’ they’re getting. Sometimes I’m speaking at conferences as ‘Elena from Lovable.’ But if someone is trying to sponsor this newsletter, they have to know that this doesn’t give them Lovable privileges or access or anything else - that’s just ‘Elena the very public PLG enthusiast.’

Mind the overlap

So, keeping the right people in the loop is half of it, but the other half is figuring out which boundaries need to be drawn.

Who owns the audience?

We’ll start with the easy one - whose audience is this? Mine! All mine. No touchie!

I’ve spent hundreds? Thousands? Of hours of my life creating this content and building relationships with you nice people, and getting to maintain my own audience across all these companies is something any employer is gonna have to try to pry from my Orangetheory-enhanced grip.

Whose time is it?

This can get bad without any bad intent at all - both my full-time role and my creator biz take time, and can grow faster if I put more time/thought/energy into them. There’s always some block on my schedule that could go toward the company paying me a salary or toward the business that I personally own.

So this is another one that is easier because I’ve set expectations for myself and been clear with the Lovable team. It’s actually different at different roles I’ve had, but my policy right now is Lovable work has to come first. Fortunately, I don’t have to fight too hard to carve out time for my writing and online conversations, because my posts often lead to more traffic and attention for the brand. So I know that it’s helping the company, too. But if I’m up against a deadline or need to travel, then my content will get pushed back.

Whose opinion is it?

This one is very clear to me, but I wish it were more clear to everyone else: My opinion is (almost always) just my opinion.

I didn’t fully appreciate this until Lovable, but now I can’t get away from it. Before, when I wrote about hiring or pricing or management or what I thought of AI, people realized it was just me sharing my perspective. Now, because of my very visible work at Lovable, people are sometimes interpreting stuff I post as an official statement from the company. Even if I never mention the company, or I’m writing about something completely unrelated to my job. Even if I directly say I’m just speaking for myself!

I hate this. I don’t want to stop thinking out loud. Stuff happens so fast now, and I think it’s valuable for me to be able to share my reactions and observations, without putting on the CorpoBot filter.

That’s how I feel about people I follow - I want to hear their for-real, unfiltered takes. I wanna know what they actually think, including the opinions that are half-baked, highly debatable, and even sometimes laughably wrong.

But I also totally get why people make this connection. I’m proud to be associated with Lovable, so it’s not really fair for me to get mad if people… associate me with Lovable. My behavior does reflect on Lovable to some degree. And people may assume that my opinions are part of the company marketing machine, or that I’m just saying something because I was told to, even when I’m totally not. I can’t control every interpretation of what I say.

I haven’t figured this one out. But the rule I’m trying to follow is just: Always try to be clear when I’m speaking for Lovable. And if something is Lovable-adjacent, but I’m NOT speaking for Lovable, I also try to be very clear about that, too. But outside of that, please just assume that stuff I say/write is you getting a look straight to the inside of my thoughts-still-in-progress brain.

Who owns the internal context?

Oof, this one gets tricky. The fact that I’m in the weeds with a company gives me all the context that makes my perspective credible and interesting. But being in The Room Where It Happens gives me access to tons of info that is not public knowledge.

So what are the boundaries between my honest takes based on my internal experience, vs. revealing insider information that could hurt the company? Yeah. Tricky. Internal numbers, our specific strategies, failed experiments, private decisions, etc etc etc. I’m sure lots of people (especially our competitors, lol) would love to hear all about that stuff. And it is very interesting. But I need to maintain boundaries around what is okay to share with the outside world.

Fortunately, Lovable’s very committed to the whole Build In Public strategy. We share a lot on purpose, and there’s an awesome culture of being open and honest, even about the hard stuff. But that doesn’t mean that company secrets or every internal conversation is up for grabs.

Who owns the brand credibility?

This one has got to be the messiest. A ‘brand’ is all about associations and mental connections and how people see you. This is where it’s nice having things all lined up, where my personal content supports my full-time work and makes everyone’s brand better.

But I still try to be super careful when it comes to situations where it seems like my personal brand is benefiting from the Lovable brand.

Like, when a company wants to sponsor me, or an event wants me to be a speaker. Are they asking about this because of my content and my personal brand? Or is this because of my role at Lovable?

And that’s where the expectation setting comes in. Especially when money is changing hands, I’m always ultra clear when I’m operating as “Elena the Content Creator” and “Elena from Lovable.”

And I’m also careful about how a connection might reflect back on Lovable - because ‘they’re not a direct Lovable competitor’ isn’t enough anymore. These days, direct competition is just scratching the surface of potential conflicts of interest - lots of other orgs are potential partners, vendors, customers, or acquisition targets. Which means my interactions with them could reflect on Lovable. And with how fast AI products change, any company that is firmly in one of those buckets is just as likely to launch a directly competitive product in the next day or two.

It can be so hard to tell. So I’m always a bit cautious. To the point where even if everything lines up on paper, I may not do it.

If it feels weird, walk away.

I tried to map these out as rules, but the lines can be so wavy. So, I just say: when in doubt, bail out.

There have been opportunities that were probably fine, not competitive, fully disclosed, and crazy good money that I still didn’t end up doing. Something about them just felt off. Usually because I could imagine someone seeing the post or whatever and misunderstanding my incentives or motivations. Or because I noticed myself doing serious mental gymnastics to explain to myself why it was technically okay.

I’ve learned not to spend too much time talking myself out of that feeling. The trust I’ve built with you, with my employer, with sponsors is all stuff I can’t get back. It’s not worth putting that at risk.

Like, for me, one of the big ones is sponsored social content - it’s definitely not wrong, but it feels… muddy. Since my social presence is much more tied to my day-to-day ops stuff, dropping a paid endorsement for another company into the stream feels a bit off for me, even if it’s totally disclosed.

So I’ve handled that by separating surfaces - I don’t do #ads on LinkedIn, but this newsletter works more like a standard media property, where sponsors are a normal part of the biz. But even then, I’m pretty selective about who I let sponsor these posts - in general, it’s only products I use or am at least exploring, so that I feel good recommending that you spend your time checking them out.

That’s kind of my point through all of this: Being an operator-creator is an amazing flywheel. Solving hard problems for cool companies means great stories and insights that turn into interesting content. Interesting content attracts large groups of interesting people. And having access to all of these interesting people helps to connect me to more great companies and their lovely challenges. It builds over time and can for sure be a win for everyone.

Just as long as you don’t get too greedy. Don’t try to cheat on either side. Don’t share info that your company would be mad about. Don’t spam your loyal audience with feature launch announcements that aren’t relevant to them, or the product ads that you’d never use yourself. Just pay attention to the tricky overlap spots and be honest with your boss(es) and you’ll have a much better shot at keeping control of your multiple personalities.

Edited by Jonathan Yagel.

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