u/Soccer-Plane-444

What are the best/most interesting startups in the aviation or travel space? 🤔

I (37M) have been running a solo web design business for ~10 years. Was at a marketing agency for ~5 years before that (right out of college).

Early on, I was really driven & fulfilled by it. Building it, creating it, growing it etc. Working 6-7 days a week, completely locked in. Didn’t even feel like work basically ever lol.

My model was simple – build (or redesign) sites, then move them to a monthly retainer (hosting, security, support). The goal in my head was always ~40-60 clients at $150–200/mo.

• Fast forward to now & that drive/spark is gone. I feel defeated. I've been at a glass ceiling of 25 clients.
• Feeling deeply burnt out & honestly like my whole professional skillset is commoditized. There's a grief aspect to this that I wasn't able to build it to align with my vision.
• Income is OK right now but ~40% of it comes from two bigger retainer clients & I know those won't last forever.
• My main lead sources over the last couple years (for new builds/redesigns) have dried up & I didn’t realize how much I was relying on them.
• I started a relationship coaching business 6mo ago that actually feels really aligned/energizing/exciting for me but not making real money yet.

So I’m in this weird spot...

The person I am today is not the one that started that business a decade ago. I've grown, changed, & evolved.

So, thinking longer-term, part of me is questioning if I go back to the 9-5 world to "reset" a bit...but I have no idea where I’d even fit in.

ADDING UPDATE NOTE HERE: someone in the comments mentioned my vibe is very startup-y & I didn’t even think about that. I'm intrigued with that space. Could fit me well – not as isolating as doing everything on my own while simultaneously not as rigid as a 9-5

I’ve never followed a traditional path/climbed the corporate ladder. Always followed my intuition & that led me to doing my own thing relatively early on. Before working remotely or being an entrepreneur was *the cool* thing to do.

I know I bring value to the world but it’s not super easy to explain or feels tangible. It’s more like I can walk into something & immediately see what’s off, what needs to change, where things aren’t aligned. It’s not “web design” or website/digital specific. It's bigger than that. I just don’t know what kind of job that would even translate to.

Curious if anyone else has been here (long-term self-employed to considering going back to a corporate job).

How did you figure out where you fit? And how did you explain your background in a way that actually made sense to employers?

Any thoughts/feelings/advice here is appreciated. Thank you so much for reading all of this 🙏 this has been weighing on my mind & heart.

I remember years ago (probably close to 10 years) listening to a podcast where a guy would send a full-on cake to his ideal clients/prospects. I don't remember the specifics but probably included some kind of note with it & a follow-up sequence. It worked well for him. For whatever reason, that idea has always stuck me & I loved how unique it was.

What's your most outside the box cold outreach idea (that you've tried or have heard of)?

How important is verification on Hinge? I've been on the app since before it was a thing so never thought twice but recently am noticing most of the women I'm looking at/swiping through are verified. Does this matter to you when you're on the app or deciding who to match with? I know we can all say "of course it does!" My gut says in theory it does but in practice, if someone really is interested/intrigued in your profile, it's not going to make or break matching/at least starting a convo. Interested in others thoughts. Thanks!