For Parents of Twenty-Somethings - Jess Diamond Coaching

Being The Parent Of A Twenty-Something Can Be Hard!

You’ve reached a new parent-child dynamic that you’ve never navigated before where they’re legally an adult, but not necessarily acting like one. You find them leaning on you for support and simultaneously craving their independence… talk about an emotional roller coaster!

Let’s face it, this generation of twenty-somethings is different… The challenges and obstacles facing them today is different from when you were in your twenties and it’s why your young adult needs some added support that comes with this stage of life!

You Love Them, And....

They won’t take the advice you’re giving.
You’re ready to be an empty nester.
They are having a hard time navigating adulthood.
You’re afraid you’ll be supporting them for the next decade.
Every conversation seems to go sideways.

Watching your kid struggle to find their way as a young adult is not a fun experience for anyone involved.

I know you want to help: not nag, not lecture, and definitely not make things worse.

Believe me… it isn’t easy for you just as it isn’t easy for them!

Why Your Twenty-Something Won't Listen To You
(and what to say instead).

If any of this sounds familiar, know that you’re not alone!

This is a universal experience for post-pandemic parents of twenty-somethings...

The world is different.

Jobs are harder to land, in-person connection feels foreign, the ability to work for 8 hours a day dissipated 6 years ago, and the challenges this generation faces are only increasing.

The good news?

You aren’t failing as a parent and your twenty-something isn’t broken!

However, there is still a gap between you, your young adult and the guidance they need.

This is where I come in!

I’m Jess Diamond, The Adulting Coach to help twenty-somethings get their sh*t together and feel confident in who they are, what they’re doing, and where they’re going [in life].

I specialize in helping this generation because I lived it. I graduated college in 2019 and struggled to find my way through the first half of my twenties, needing a coach to guide me. Only it didn’t exist yet!

That’s when I knew I needed to become a Certified Life & Nutrition Coach and Personal Trainer and combine these certifications with research and personal experiences to become THE resource to help my fellow twenty-somethings succeed.

Your kid needs someone in their corner who isn’t you. Not because you’re a bad parent, but because they are able to open up and listen to someone who speaks their same language and knows the struggles they’re facing based on the current climate of the world. That’s where I come in!

What Parents Are Saying:

When Gale first came to me about working with her daughter, her heart was breaking for her recent college grad struggling to find a full-time job. Leah had a part time job and desperately wanted help with different approaches to finding something related to her career as a graphic designer. She lacked confidence in her portfolio, networking abilities, and not having the 'right' answers. By the end of our coaching partnership, Gale watched her young adult transform into a woman who was actively reaching out to people, hearing back from companies, and feeling so much more hopeful around her career. Not only did Leah operate in her life differently than before, but Gale's stress was alleviated knowing that her daughter was in good hands, giving Leah the help she didn't know how to provide.

Sherry has sent two of her daughters to work with me through their freshman year. Her eldest daughter advocated for a Life Coach to help her adjust to college. We didn't realize it would quickly turn into navigating a debilitating break up and feeling defeated for picking the 'wrong' school. After a few months, Sherry exclaimed, "You're the best thing to happen to my family this year!" I helped Cassidy navigate her breakup and transfer from Brandeis to NYU where she just graduated in May 2026. In return, Sherry has not had to worry about the state of her daughter's well-being. A few years later, her second daughter was having a hard time with school, time, and anxiety. She failed her first semester, then decided to work with me to help her figure out her relationship to school. Jasmine now has a clear direction on what she wants to do career wise and confidence in her decision to switch to Cosmetology school in the Fall!

Juan called me, worried about his daughter. She just graduated college, moved to a new city, and was having a hard time getting out of her apartment and finding a full-time job. AnaLuna and I quickly got to work where she was able to develop a routine that worked for her, leave her apartment daily, and land a full-time position! Juan was no longer worried about his daughter trying to navigate adulthood on her own and loved that she had someone in her corner close to her age who understood what she was going through. AnaLuna felt like she had a friend, big sister, and coach all at the same time where she felt comfortable talking to me and listening to what I had to say.

Ryan's mom, Terry, found me after having to pay her son's rent to avoid eviction... again. She was fed up with how irresponsible he was around his money, life, and decisions, and needed someone to help him get his act together. Ryan and I worked a lot of budgeting, habits, and relationships to the point where he was paying rent on time every month and still had money leftover to spare! Terry still worries about her son, but what mom doesn't? At least now she doesn't have to worry about him getting evicted.

How You Fit In The Coaching Picture

While I do view coaching as a team sport, where we all share the common goal: helping your twenty-something succeed, it is important to note that the client-coach relationship remains confidential.

Which means, you will not be left in the dark, but you will not be given details discussed during our sessions, unless spoken from then mouth of your young adult.

The team aspect comes into play across three different ways:

1. Initial Conversation

Before anyone says yes to any coaching, I meet with you to understand your perspective of what’s going on in your twenty-something’s life. This is what your free 30 minute call is for, as well as a place to determine if coaching with me is your twenty-something’s best next step.

Book a Call Here

2. Parent Check In Calls

When a parent is financially invested in the success of their kid, I provide two check in calls throughout the initial 12 week journey. One occurs halfway through and another towards the end of the 12 weeks. The best part? The check ins continue on as needed, after the fact, as long as your young adult is still coaching with me! During these calls you’ll receive an overview of progress, what we still plan to work on, any concerns you or I may have, and actions you can take to best support your young adult.

3. Ongoing Communication

During my coaching partnership with your twenty-something, not only do they have constant communication with me, but so do you! You can message me via email and text where you will be able to express your concerns or provide feedback along the way.

You didn’t come this far as a parent to watch them stay stuck. One 30-minute conversation could change everything for both of you.

Client Testimonials

"Before coaching with Jess, I felt stuck, like I was glued to the ground and didn’t really know where to go. On top of that, my relationship with my parents was really bad for a bunch of reasons. Having someone to check in with, who could help motivate me and give practical tips and suggestions to guide me, made a big difference. Jess gave me systems for my routine, my job search, and saving money. I feel like myself again and know what I'm working towards and am capable of."

"I struggled with getting a job after college and figuring out this whole “adulting” thing. Jess helped me get out of my apartment, meet people, and land my first full-time job! Now I feel really good about the life I'm building in my new city."

"I was unsure about coming back to school or what I wanted to do with my future: find a job in the DC area, come back, transfer… the options were there, but returning wasn’t very high on my list. Jess helped me with my routine so I could stay on top of my school work, organize my thoughts into actions, and decide to go return for my Sophomore year."

Jess Diamond Coaching

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