Long Story Short
Reaching out to a real human almost always moves things further in 15–20 minutes than hours of going solo ever did. And the people on the other end? They’re almost always excited that you asked! We built you the Reach Out Anyway Toolkit — with REAL emails — so making the ‘ask’ feels easier, more normal, and something we all do more often.
Jump to How!
I’m really good at sales and fundraising. I don’t know why or how, maybe something honed after YEARS of being in those jobs. Maybe something innate and that I’m just meant to do. Who knows, but it feels comfortable.
At the exact same time, I’m REALLY bad at building the system, the knowledge, and everything wrapped around it.
It’s pretty easy to bring in revenue:
- Make a list of everyone you know and/or everyone you WANT to work with.
- Start reaching out to 3–10 folks a week.
- Build a pipeline (Google Sheets works!) and meet every week to track it.
It’s the same over and over and over — and it works.
But what’s all the stuff that comes around it?
I’ve been struggling with this at Helia. A lot. The big vision is that Helia is the place that doers come when they need help.
Today that looks mostly like folks reading our newsletter and articles and then hiring Helia itself for consulting engagements or asking me (Jess) directly for connections to Helia Collective members that are experts in areas where Helia doesn’t consult.
In the future, we want it to look like 90% of our site visitors getting the help they need from articles, and that other 10% hiring Helia Collective Members directly. (And maybe I have 1-2 executive coaching clients at any one time.)
But the path from here to there? It isn’t nearly as clear. I know how to work the system — and I know it will work eventually.
But when Helia’s COO, Libby Fischer, wants to get a sense of when we can pay her full rate (versus the half rate she agreed to as we both throw ourselves into building Helia)? Or when my Consulting Partner, Andrea Chen, asks if the way we’re pricing is going to help us hit our financial goals?
I legit can’t answer. And, well, it’s embarrassing.
I know we’ll get there. I can always do more and work harder and I KNOW I can bring in the revenue. But the bigger picture that it’s a part of? There’s a reason every few months I have a week of panic — will this work? How will it work? What do I need to do?
A few weeks ago, in the middle of one of those panic weeks, I did something a little different. Before I called Andrea, I went and read a bunch of Helia articles, including Andrea’s piece on fundraising. It was kind of good and kind of weird, this meta moment of reading the thing I’ve been building. I got real grounding just from that. THEN I reached out to Andrea and asked if she’d talk me through it.
Within 15–20 minutes of finishing that conversation, I had such clarity about what needed to happen that I could go back to Libby with a real answer. I updated the models. I sent something really simple. I felt strong and good.
It was another reminder of something I’ve been re-learning my whole career: when I’ve been stuck, a conversation with the right person has moved more in 20 minutes than hours or weeks of going solo or talking with Claude ever did.
The learning? Reach out. Every time.
Reaching out isn’t a break from the work. It IS the work.
The conversations that sparked Helia
This isn’t a new lesson for me. It’s THE pattern of my career.
When I was spiraling about over-involvement at work — feeling like I couldn’t do my job unless I was also fixing everything else around me — my cousin Amy Millard (a serial CMO in tech) gave me an image I still come back to. She said: “Imagine you’re driving down the freeway and there’s a car burning on the side of the road. You’re not getting out and you’re not going to fix it, not because you’re not a strong, capable human, but because you have no idea how to jump into a car fire or save someone. Your presence trying is probably going to get in the way of the people who DO know what they’re doing. What you CAN do is call the fire department. You can pull over a quarter mile away and be ready if there’s a call for help. And you can really hope the people who know what they’re doing are already there, because they usually are.”
That one conversation — probably 15 minutes — reframed how I thought about my role at work, and honestly, about my own sense of self-importance in the chaos I was sometimes causing. I’ve been working through it ever since.
When I was over- AND under-forecasting revenue month after month, Amy (same cousin, different hat) gave me a few tricks that literally made me able to breathe again — and reduced everyone’s stress around me.
When internal comms felt brutal at work, I asked Kate Schmidt — an expert communicator who happens to be my friend’s wife — how her company handled it. I walked away realizing it was hard everywhere, AND that there were so many better ways to do it.
When I was trying to figure out how to start Helia and what it should even look like, my friend, Marina Nitze said, in maybe a 15-minute conversation: “Do some User Experience (UX) testing. Just call a few users and ask them what it’s like to use Helia.” I was like, ‘Oh. Yeah. Good reminder. I did — and of course every conversation unlocked something I wouldn’t have gotten to alone. (Shout out to Shantell Steve, who I ended up having a spontaneous coffee with a few hours later, which gave me a million new ideas.)
Every single one of these is a conversation I almost didn’t have because the version of me in my own head thought she should be able to figure it out alone.
These are LITERALLY the conversations that sparked Helia. When I was thinking about how I’d learned the most in my career, it wasn’t the academic articles (though I read them, and they gave me some things). It wasn’t frameworks. It was real people, sharing real wisdom, in conversations that often lasted less time than it takes to read a blog post. I wanted that to exist as a thing people could actually come to over and over again, with whatever they were sitting with. That’s the Helia Library.
The Key Takeaway
Reaching out isn’t a break from the work. It IS the work.
A thoughtful ask to the right human almost always moves things further in 15 minutes than you’ll move in hours on your own. The people on the other end, even the ones you’re nervous to bother, almost always want to be asked.
The only move that matters is hitting send.
The Four Moves
If you’re a “just give me the moves and I’ll go” kind of person (aka Helia’s COO Libby), here they are:
- Reach out earlier than feels comfortable — before you’ve figured it out, not after
- Make the ‘ask’ specific AND easy to say no to — name the thing; give them a clean no
- Listen for what you actually needed — sometimes a tactic, sometimes a reframe, sometimes just being seen
- Close the loop — come back and tell them what happened
That’s the whole thing.
If you’re a “tell me the texture of each one, give me the stories, let me see it play out” kind of person (aka me), read on.
How These Moves Actually Work
1. Reach out earlier than feels comfortable
My default, and maybe yours, is to try to figure it out first. Read the articles. ChatGPT the question four different ways. Stare at the doc. Rework the spreadsheet. “Let me sit with this a bit longer and see if it comes together.”
Sometimes it does. AND — what I keep re-learning — is that the conversation with a human that I eventually end up having WAS GOING TO UNLOCK IT, whether I had it at hour 2 or hour 10. The going-solo time didn’t make the eventual conversation more efficient. It just made me more tired going in.
With Andrea, the reading I did beforehand did help — I came in with better context and better questions. But I could have reached out a week earlier and been fine.
The rule of thumb I’m trying to hold: if you’ve googled the thing twice and still aren’t sure, the next move is probably a human.
A thoughtful ask to the right human almost always moves things further in 15 minutes than you’ll move in hours on your own.
This is easier to accept in the obvious moments. If you’re job searching, you already know to reach out. And the second the role you wanted closes, reach out to the hiring manager anyway. Tell them what you loved about what you read, what you’ve done, what you want to do. Acknowledge the moment’s passed. Shoot your shot. As a hiring manager, I would LOVE to receive that note — it means someone is actually into it, not just applying for their umpteenth job. Same with fundraising: the donor who just said no this cycle is the one you check in with in six months.
The reaching-out muscle is the same muscle in the messier moments. Stuck on cash flow? Think through every company or org you know that’s been in a tight moment, and anyone in accounting or finance in your world — folks you worked with, your cousin(!). Send a note with a couple bullets on what you’re trying to decide, how you’re thinking about it, and ask for their favorite resources OR 15 minutes. It’s the exact same move.
2. Make the ask specific AND easy to say no to
This is where outreach most often goes sideways, mine included. “Can I pick your brain?” isn’t an ask. It’s a vibe. It puts all the work on the other person to figure out what you actually want.
What works:
- Name the actual thing. “I’m updating our pricing model and trying to think through tiered vs. flat rates. You wrote about fundraising pricing recently and I’d love your brain on this for 20 minutes” is a real ask. “Would love to pick your brain about fundraising” is not.
- Give them a clean no. “No pressure if the timing doesn’t work — feel free to tell me to try again in three months.” This isn’t softening the ask; it’s honoring their time.
- Match the channel to the relationship. A quick question to someone you talk to weekly? Text. A bigger ask of someone you haven’t talked to in two years? Email, with enough context that they could say yes without needing a call.
Jess’s Sent Folder has real examples from my actual sent folder. The email I sent about Senior Leadership Team meetings, the one I sent when I moved to LA (which doubled as a job search + a life-transition ask), the one I sent asking for eyes on a work-in-progress, the follow-up I sent after someone helped me. Pull from whichever is closest to what you’re trying to do.
3. Listen for what you actually needed
This one surprised me, and I keep learning it in new ways.
Sometimes what you need is tactical. Andrea knows pricing. I had a thing to solve, she had the expertise, I needed what she knew. Clean handoff.
Sometimes what you need is a reframe you didn’t know you needed. Amy’s car-fire image didn’t solve my tactical problem. It reshaped my conception of the problem itself. I went in thinking “how do I fix all this other stuff around my job” and came out realizing I was often the chaos, and that my actual job was to pull over and let the right people do their work.
Sometimes what you need is just to be seen. A real human saying “yeah, that sounds really hard” can change how you feel about your week, even if they don’t tell you what to do.
The trap is going in with a narrow ask and shutting the conversation down before the real gift shows up. Ask your actual question AND leave space for the person to notice something about your situation you didn’t see yourself.
If you’ve googled the thing twice and still aren’t sure, the next move is probably a human.
4. Close the loop
This is the one I forget most. And the one that matters most for the long game.
When someone gives you their time, come back. Tell them what you did with what they said. Thank them specifically. NOT “appreciate the call” but “the car-fire thing is changing how I approach my whole week — here’s what I did differently.”
This isn’t about performing gratitude. It’s about closing a loop that would otherwise stay open — in their head (did that help her?) and in yours (am I someone who takes and disappears?). Closing the loop is how one conversation turns into a relationship you can keep coming back to.
I keep a running list of people who’ve helped me with specific things, and I try to circle back within a few weeks. Those follow-up messages often turn into the richest ongoing conversations I have and, honestly, they’re often when the second, even better idea shows up.
The Other Side: Being Asked Feels Good
Here’s the part I keep forgetting, and that I think we all keep forgetting:
When someone you know reaches out to you thoughtfully, and you can help, it feels GREAT.
Being asked for your wisdom, your experience, your take on something — that’s not a burden most of the time. It’s a gift. It means someone thought of you. It means they trust what you’ve been through. It means the hours you spent figuring that thing out aren’t just sitting in your head. They’re useful to someone else.
Now, I don’t want to pretend everyone can always say yes. Some people are fielding thousands of emails a day or hundreds of requests a week. Sometimes the answer is no. Sometimes the answer is no answer. That’s okay. Keep going.
Be thoughtful — always. Who you ask, when you ask, how you ask. Don’t send the same note to 400 people. Don’t ask a stranger for an hour of their time with no context. Don’t treat people like a vending machine for advice.
AND don’t psych yourself out in the other direction either. The version of you that doesn’t send the email because “they’re too busy, they won’t respond, this is silly” is robbing both of you. Robbing you of the answer. Robbing them of the chance to help, which, I promise, most of them will be glad to do.
The rule I try to hold: make a thoughtful ask. Then let them decide whether to say yes. That’s not your call to make for them.
When Reaching out Feels Hard
Sometimes the thing stopping you isn’t the logistics — it’s you, or your actual situation. A few things I’ve noticed:
- If you’re embarrassed to ask: that’s almost always the signal that this is exactly the ask you need to make. The stuff we’re embarrassed about — “I should know this by now,” “this is too basic to bother someone with” — is usually the stuff we’ve been spinning on the longest. The people we’re worried about bothering almost never see the ‘ask’ as basic. They see someone trusting them with something real.
- If your network feels thin: start with what you have, and grow from there. Jesse Noonan’s job-search series in the toolkit is LITERALLY about this. Over seven months, she turned every ask into a growing list and every yes into an introduction. It’s the clearest example I’ve seen of someone using a job search to actually deepen a network, not just activate it.
- If you’re worried about being transactional: the fix isn’t to not ask. It’s to close the loop and make it about the relationship over time. A one-time ask feels transactional. A conversation you keep coming back to — celebrating their wins, asking again six months later, having something to offer back — is just what it looks like to be in each other’s lives.
- If you don’t know who to ask: sometimes the first useful ask is “who would you talk to about this?” The people close to you are often better at surfacing the right person than you are, because they see you and them from different angles. (This is also LITERALLY what Helia is for — if you don’t have the right person, we probably know someone who does.)
Jess and her son, J!
If You Want Help
I (Jess) love this kind of work — sitting with someone who’s stuck, helping them figure out who to reach out to, what to say, how to think about it. I do this as ongoing thought partnership / coaching with a handful of leaders at a time, and I’m always happy to do a one-off session to help you figure out your list, your ask, and your next move.
I’m probably a good fit if:
- You’re sitting with a specific hard thing (a decision, a strategy, a people situation) and want a second brain on it — AND help figuring out who else in your world to pull in
- You want ongoing thought partnership — someone to check in with as you’re navigating a stretch of hard stuff
- You’re doing a job search, fundraising push, or major transition and want help building the muscle of reaching out consistently and well
- You’re trying to figure out who to talk to and your own network isn’t surfacing the right person. Between my network and the full Helia Collective, we almost always know someone
Connect with Jess!
Try This Yourself
Jess’s Reach Out Anyway Toolkit
- Jess’s Sent Folder: Real Emails + Templates — real emails from my sent folder, organized by the five situations outreach usually falls into
- Jesse’s Job Search Series — Helia Collective member Jesse Noonan’s complete seven-email series from a seven-month job search, built with coach Eric Woodard
Recommended reading:
- The Ask Approach by Jeff Wetzler — a beautiful framework for staying curious and expanding who you’re learning from (TEDx talk here)
Questions to Sit With
- When I’m stuck, what’s my default move? Is it giving me what I actually need, or just making me feel productive?
- Who’s someone I’ve been meaning to reach out to for months — and what’s actually stopping me?
- What am I embarrassed to ask about right now? Is that embarrassment a signal this is exactly the ask to make?
- When someone helps me, do I close the loop — or disappear, and then wonder later why I don’t feel like I have “a network”?
- Am I building relationships I can keep coming back to, or one-off transactions?
About Jess
Jess Skylar has spent two decades learning — over and over and over — that the thing unsticking her was almost always a 15-minute conversation with a real human. She finally started Helia because she wanted the thing she kept needing to exist for other people, too.
She is trying very hard to reach out earlier these days. Still working on it.
This article comes from Jess’s own pattern of reaching out, over and over, and learning each time. These conversations, and the ones you’ll hopefully start having too, are the heart of the Helia Library. We don’t need to start from blank pages, or do everything alone.
As always, take what’s helpful, leave what’s not, and make it your own.
