Reworkit with Jess Wass: Chasing Dreams & Influence
Published 19 days agoย โขย 6 min read
Hi Reader,
TLDR:
Don't Wait on Your Dreams: I'm doing something I've always dreamed of doing, but almost talked myself out of it. Learn what I'll be doing the entire month of May.
The Entrepreneur DNA Podcast: I was recently a guest on a podcast and will share some of the key topics we talked about and how you can listen.
Need Help Influencing without Authority?: I'm sharing some of the key pieces of advice discussed in my most recent invite-only office hours session with my clients.
Don't Wait on Your Dreams
I'm doing something I've always dreamed of right now. And I almost talked myself out of it.
For the entire month of May, I'm trading New York City for Southern California. San Diego County, Orange County, Santa Barbara, maybe Los Angeles if we can squeeze it in. A full month, not a vacation, not a work trip. Both.
Here's the backstory.
When I started Reworkit, one of the quiet dreams underneath the business was this: no office, no strict PTO policy, the freedom to work from wherever I wanted. My partner and I have gone back and forth for years about whether to eventually move from the East Coast to the West Coast. We have family and friends in both places, but our roots are in New York. So we landed on a different idea: what if we didn't have to choose? What if we spent two or three months a year in SoCal, enough time to really live there, without committing to a full move?
It was one of those dreams I kept in my back pocket. Someday. When the timing is better. When I was rich and famous and could afford two houses. You know, a pipe dream.
Then I landed a keynote speaking opportunity about an hour from my in-laws in Southern California. We visit them for a week or two every year. The trip was already happening. The pieces were right there. And I thought, what if this is the moment?
And then immediately, my brain served up every reason not to.
My partner has a regular job, limited PTO, an in-office policy. Our daughter would have to be pulled out of daycare and managed full-time by us for a month. We'd be living in someone else's house. It would be complicated and imperfect and a lot to coordinate.
All true. Also: completely beside the point.
Because here's what I've learned. There are always reasons not to do the thing. There is always a voice that says wait until the timing is better, wait until life settles down, wait until you've earned it a little more.
That voice sounds responsible, but it's actually just scared. Scared of what it means to actually go after something you want. Scared of the possibility that it could be really good.
I also had to get honest with myself about something harder. There is no guarantee that next year will be easier or that a better time is actually coming. Parents are getting older. The world is unpredictable. Nobody is owed tomorrow. And I don't want to be someone who kept waiting for permission to enjoy her life.
So we're going.
Maybe it'll be chaotic. Maybe it'll be magical. Maybe I'll drag my husband to an open house and spend the whole drive back floating the idea of actually moving while he quietly regrets his life choices. Who knows? That's the fun part! Adventure awaits!
Now I want to turn it back to you.
What's the thing you've been putting off? The trip. The phone call. The local adventure you keep saying you'll get to. The friend you've been meaning to see.
This is the sign you've been waiting for. Do it now.
Hit reply and tell me what it is. I'd genuinely love to know.
The Entrepreneur DNA Podcast
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I have some exciting news to share! I was recently featured as a guest on The Entrepreneur DNA with Justin Colby, one of the top entrepreneurship podcasts out there with hundreds of thousands of listeners. It was a really fun conversation and honestly one of those interviews where the time just flew by.
We covered a lot of ground, but a few things I know will resonate with this community:
๐๐ฝ We talked about what it really means to feel stuck, and why that sinking feeling that something is off in your career usually isn't a "you" problem. It's a placement problem. Wrong role, wrong environment, wrong fit.
๐๐ฝ We also got into how to tell the difference between quitting something because it's hard versus quitting because it genuinely isn't right for you. That distinction alone is worth the listen.
If any of that sounds familiar, go check it out.
You can find The Entrepreneur DNA wherever you listen to podcasts or watch the full episode on YouTube via the link below.
And if it resonates, I'd love it if you shared it with someone in your life who might need to hear it too.
Once a quarter, I hold an invite-only office hours session for my current and former coaching clients. It's one of the ways I make sure the value of working together doesn't stop when our official engagement does.
This past session, we got into one of my favorite topics: influencing without authority. How do you get things done when you can't just tell people what to do?
Here's what came up.
1๏ธโฃ Non-responsive people aren't ignoring you. They're overwhelmed and triaging. The fix is pretty simple once you know it: figure out their preferred communication channel, connect your ask to something they already care about, and if you're not sure how to reach them, just ask directly. "What's the best way to get you?" Also, tag people explicitly. Ambiguity kills follow-through. When everyone's responsible, no one is.
2๏ธโฃ Procrastination is a mood stabilizer, not a personality flaw. When someone goes quiet, it's usually not laziness. It's often that they don't understand what's being asked and don't want to look dumb. Simplify the ask. Try a more private channel so they feel safe asking questions. You'd be amazed how fast things start moving when people don't feel put on the spot.
3๏ธโฃ If goals aren't clear, start asking. In startup and ambiguous environments especially, everyone is secretly operating from their own version of what the goals are, even if no one's ever said it out loud. One question cuts through all of it: "What's most important to you right now?" That answer tells you everything about how to get what you need from that person.
4๏ธโฃ When you're dealing with a defensive person, start with agreement. Before you push back or introduce a new idea, find something you genuinely agree with. Then use "yes, and" instead of "no, but." And read the room: if someone is already dysregulated, it's not the time. The conversation you're trying to have isn't going to land. Come back when the temperature has dropped.
If any of this hit close to home, managing up and influencing without authority are exactly what I help people get good at. Whether you're stuck in a dynamic with a difficult stakeholder, not getting the visibility you deserve, or just tired of feeling like you're pushing a boulder uphill, let's talk.
Reply to this email or use the link below to book a call with me and we'll figure out if coaching is the right next step for you.