Jessica Sweet, CPCC, CEIP, LICSW

Executive Career Coach

Wishingwell Coaching

I am The Career Therapist. What does that mean? I help with all those sticky places where your mindset and emotions overlap with work. 

Getting clear on what you really want. 
Achieving that next level. 
Managing your anxiety. 
Stopping limiting beliefs or patterns that hold you back. 
Creating work life balance. 
(Re) Building confidence. 
Being the leader you really want to be. 
Putting all of your ADHD magic to work for you. 
Setting boundaries
Dealing with burnout. 
Recovering from toxicity
And more. . . 

WHAT YOU WANT:

You want make an impact, make money, find a great corporate culture, grow, learn and feel like you’re contributing. 

Is that really so much to ask? 

Nope.

But you know that you’re holding yourself back, and sometimes you wonder: do you need a therapist, or a coach?

How about both?

As a trained therapist (Harvard Teaching Hospital Psychiatry Training Program) and a certified coach x 14 years, I can help you feel empowered. 

WE COULD:

✔Gain the confidence to get a new job or advance even if you have battle scars from previous roles, haven't job searched in years, or feel stuck and confused.
✔Get past mindset blocks holding you back from having the career you want
✔Reset your boundaries
✔Make a career transition and find a job and company that's exciting, a match for your skills and experience, and pays!

SOME OF MY WINS INCLUDE:

✔Coached 100s of clients over 14 years to 6/multiple 6 figure jobs doing work in alignment with their values, skills and experience
✔Helped several clients start their own business
✔ Invited to write articles for/quoted in several leading business + career publications, including Forbes, U.S. News and World Report, The Huff Post, CNBC, Business Insider, Monster.com, and more
✔Helped clients increase salaries by as much at 100%
✔ Top 25 Career Coach + Forbes Coaches Council

If you're stuck, feel you're wasting your potential, or feel like we should talk, message me on LinkedIn or: jessica@wishingwellcoach.com

Executive Career Coach for Midlife Leaders

Forbes Coaches Council

I'm a member of this invitation only organization for leading career and business coaches.  My articles on career coaching, job search and strategy have been accepted and published on Forbes.com. Read them in my publications section. Collaborated with some of the top minds in the coaching industry.

Official Member

Executive Connexions Ltd.

Cambridge Health Alliance

Licensed Clinical Social Worker

Trained under top trauma specialists to learn about and practice cutting edge trauma treatment, and treat patients in 1-to-1 and group therapy settings.

Victims of Violence Fellow

Montgomery County Methadone Center

Counselor

My father hated his job but stayed for 30 years to support our family, even though it made him sick and angry. He could have done a million other things, but he couldn’t see the options. Instead, he was miserable until the day he up and quit. 

The rest of the family suffered, too. 

My first job was toxic and “not me." I quit without notice. 

𝗜 𝗸𝗻𝗼𝘄 𝗳𝗶𝗿𝘀𝘁𝗵𝗮𝗻𝗱: 𝗮 𝗷𝗼𝗯 𝘁𝗵𝗮𝘁 𝗺𝗮𝗸𝗲𝘀 𝘆𝗼𝘂 𝗺𝗶𝘀𝗲𝗿𝗮𝗯𝗹𝗲 𝗶𝘀 𝗻𝗼 𝘄𝗮𝘆 𝘁𝗼 𝗹𝗶𝘃𝗲. 

You’re not the kind of person who can feel one thing and do another.

💔 Your career isn’t working, and you're feeling: 
	
➔ Stress, 
➔ Burn out,
➔ Undervalued, 
➔ Mis-matched/Confused/Unfocused
➔ You need a job that's more than a paycheck

➡ You’ve wished for a career coach who can help with difficult emotions, 𝙖𝙣𝙙 has a solid, proven system. 

𝗧𝗵𝗮𝘁'𝘀 𝗺𝗲.  

⭐ 𝗠𝘆 𝘀𝗽𝗲𝗰𝗶𝗮𝗹𝘁𝘆 𝗶𝘀 𝗰𝗼𝗮𝗰𝗵𝗶𝗻𝗴 𝗺𝗶𝗱𝗹𝗶𝗳𝗲, 𝗽𝗲𝗼𝗽𝗹𝗲-𝗼𝗯𝘀𝗲𝘀𝘀𝗲𝗱, 𝗵𝗶𝗴𝗵 𝗘𝗤, 𝗝𝗮𝗰𝗸/𝗝𝗶𝗹𝗹 𝗼𝗳 𝗮𝗹𝗹 𝗧𝗿𝗮𝗱𝗲𝘀 𝗯𝘂𝘀𝗶𝗻𝗲𝘀𝘀 𝗹𝗲𝗮𝗱𝗲𝗿𝘀 𝘁𝗼 𝗺𝗼𝗿𝗲 𝗮𝗹𝗶𝗴𝗻𝗲𝗱, 𝗶𝗺𝗽𝗮𝗰𝘁𝗳𝘂𝗹, 𝗮𝗻𝗱 𝗵𝗮𝗽𝗽𝘆 𝗰𝗮𝗿𝗲𝗲𝗿𝘀. 

I use effective and proven career tools + systems I’ve created + refined over 15 years, + my therapy background.

𝗛𝗼𝘄 𝗜 𝗰𝗮𝗻 𝗵𝗲𝗹𝗽: 

⭐ 𝗩𝗜𝗦𝗜𝗕𝗟𝗘, job search system + weekly group coaching + mental wellness/support. https://www.linkedin.com/redir/invalid-link-page?url=https%3A%2F%2Fwishingwellcoach%2ecom%2Fjob-search-coaching%2F

⭐𝗖𝗼𝗺𝗽𝗹𝗲𝘁𝗲𝗹𝘆 𝗖𝗼𝗻𝗳𝗶𝗱𝗲𝗻𝘁 𝗖𝗮𝗿𝗲𝗲𝗿 𝗖𝗵𝗮𝗻𝗴𝗲, 6-month group +1:1 coaching program: https://www.linkedin.com/redir/invalid-link-page?url=https%3A%2F%2Fwishingwellcoach%2ecom%2Fjob-targeting-group%2F

⭐𝟭:𝟭 𝗖𝗼𝗮𝗰𝗵𝗶𝗻𝗴, Get clear, make decisions + resolve emotional career conflicts.
https://tinyurl.com/coaching-chat

𝗖𝗹𝗶𝗲𝗻𝘁𝘀 𝘀𝗮𝘆:
“I cannot emphasize enough - if you are considering any of the topics on her page or listed above . . . - work with Jess.” Jeffrey Rapp, MBA, PHP

“I would recommend Jessica to anyone looking to resolve a career dilemma!!” Julia Wooding, MBA

“Her personalized approach, combined with her expertise and encouragement allowed me to make significant progress and achieve remarkable results in a short period of time.” Tim Freeze, Sales Leader

𝗬𝗼𝘂 𝗰𝗮𝗻 𝗯𝗲 𝗺𝘆 𝗻𝗲𝘅𝘁 𝘀𝘂𝗰𝗰𝗲𝘀𝘀 𝘀𝘁𝗼𝗿𝘆.
	⇨ Send me a DM and let’s chat.

𝗙𝗿𝗲𝗲 𝗖𝗮𝗿𝗲𝗲𝗿 𝗥𝗲𝘀𝗼𝘂𝗿𝗰𝗲𝘀: 
https://wishingwellcoach.com/career-resources/

Jessica Sweet, CPCC, CEIP, LICSW 🇺🇦

ADHD Career Coach | Founder of Momentum — the 8-week coaching program built to get ADHD brains off the overthinking line and into a rhythm of task execution (even on low-energy days)

If you're like most senior leaders I work with, you're not stuck because you lack experience, but because locking into your next move feels impossibly heavy.

I know that feeling well.

For years, I could lead teams, close deals, and make high-stakes decisions without blinking.

But when it came to my own next step?

– Everything blurred.
– The options multiplied.
– The second-guessing crept in.

And the longer I sat with it, the harder it got to move at all.

You can probably relate:

– You can see multiple lanes.
– You can imagine yourself in all of them.
– You can talk yourself into each one if you're not careful.

But eventually, the weight of all those possibilities starts to work against you.

➝ Your story doesn't point anywhere.
➝ Your positioning feels scattered.
➝ Your confidence nosedives.

And you start asking the real question:

"𝗪𝗵𝗮𝘁 𝗽𝗮𝘁𝗵 𝗮𝗰𝘁𝘂𝗮𝗹𝗹𝘆 𝗺𝗮𝗸𝗲𝘀 𝘀𝗲𝗻𝘀𝗲 𝗳𝗼𝗿 𝗺𝗲 𝗻𝗼𝘄?"

Most people assume it's a motivation problem.

It's not.

𝗜𝘁'𝘀 𝗮 𝗵𝗲𝗱𝗴𝗶𝗻𝗴 𝗽𝗿𝗼𝗯𝗹𝗲𝗺.

Because when you're keeping too many options open, nothing really lands.

Once you stop hedging and lock into one clear lane, 𝗲𝘃𝗲𝗿𝘆𝘁𝗵𝗶𝗻𝗴 𝗱𝗼𝘄𝗻𝘀𝘁𝗿𝗲𝗮𝗺 𝘀𝘁𝗲𝗮𝗱𝗶𝗲𝘀:

➝ Your direction locks in. 
➝ Your positioning becomes clear. 
➝ Your visibility grows in the right spaces. 
➝ Your authority increases with the people who matter.

Small wins start stacking again.

Movement feels normal.

Confidence comes back online.

𝗧𝗵𝗮𝘁'𝘀 𝘁𝗵𝗲 𝘄𝗼𝗿𝗸 𝗜 𝗱𝗼.

Through 𝗠𝗼𝗺𝗲𝗻𝘁𝘂𝗺 — my 8-week 1:1 career accelerator — I help leaders in transition stop hedging, lock into one clear path, and build visibility and authority where it actually matters.

Here's what you get:

– A structure for clarity, positioning, visibility, and authority
– The accountability and scaffolding that keep you steady
– 1:1 support to reduce friction instead of adding pressure
– A 2nd brain to guide the work between calls (Persona™)

By the time the conversations start, people already understand who you are, what you bring, and where you fit.

And once you lock in?

Momentum becomes the norm.

📩 𝗗𝗠 𝗺𝗲 "𝗠𝗼𝗺𝗲𝗻𝘁𝘂𝗺" 𝗶𝗳 𝘆𝗼𝘂'𝗿𝗲 𝗿𝗲𝗮𝗱𝘆 𝘁𝗼 𝘀𝘁𝗼𝗽 𝗵𝗲𝗱𝗴𝗶𝗻𝗴 𝗮𝗻𝗱 𝘀𝘁𝗮𝗿𝘁 𝗺𝗼𝘃𝗶𝗻𝗴 𝗳𝗼𝗿𝘄𝗮𝗿𝗱.

David Hannan

I keep coming back to this photo.

I almost didn't take it.

— Last summer
— Olivia's first day of kindergarten
— I was just focused on getting her through the door

I was 48 when I became a dad.

— Older than expected
— Less apologetic than I imagined
— Already more at peace with it than I realized

People didn't say it outright.

They rarely do, but the message was there:

— It's selfish
— You won't keep up
— She'll graduate before you retire

I didn't debate it.
I just carried on.

Last year, at 53, I walked my daughter Olivia into her first day of kindergarten.

— Her hand in mine
— Purple backpack bouncing
— That half-skip kids do when they're excited

That's when it landed: if I'd listened to them, this moment wouldn't exist.

And while that decision was playing out at home, I was watching the same pattern play out at work.

I've spent years watching people edged out after 50.

— Resumes stop getting traction
— "Too experienced" turns into a liability
— "Not a fit" says everything without saying anything

Translation: ageism in disguise.

Here's the part that's stayed with me since.

That same stretch of life is often when things click.

That was true for me.

In my early 50s, I was diagnosed with ADHD.

— A clearer view of my patterns
— A new way of working with my brain
— A reframing of everything that came before

It forced me to strip away the noise.

— Better systems
— Cleaner decision-making
— Fewer obligations I never agreed to

I grew more in my early 50s than I had in decades before.

We're sold a neat timeline:

— Career first
— Family on schedule
— Progress in orderly stages

Real life doesn't follow that script.

Some of the most important things arrive once you stop racing the clock.

I turn 54 next month.

I don't feel late.
I feel settled.

And when someone quietly decides I've missed my window, I don't feel the need to correct them.

I know what opened once I stopped believing in that clock.

P.S. A lot of people already have a "late" moment behind them.
They just haven't given it credit yet.

Helping high-performing leaders get clear on their next move and show up with confidence | Founder of Momentum | Former $4M full-desk recruiter

My client, a Head of Marketing in EdTech, recently received a $265K offer because of this:

We'd been working 1:1 to get clear on her next step after feeling stuck for months—riddled with overwhelm and imposter syndrome.

Before then, she had no clarity on what role she wanted next.

Her resume and LinkedIn profile told two different stories.

Every rejection felt personal, feeding her imposter syndrome and making it hard to keep going.

Networking felt overwhelming and random (which is fine, but not effective).

So what changed?

4 things:

1. Clearer, more specific career direction
2. Cohesive resume and LinkedIn branding
3. Targeted engagement/networking strategy

But #4 has been the wildest unlock of them all ↓

4. Consistently posting authority-building content

Once her approach changed, she not only landed conversations with key decision-makers…

But she built real momentum and started drawing the right roles without overthinking every step.

Before, her job search efforts looked like this:

— Applying to roles without tailoring outreach
— Sending connection requests with no purpose
— Hesitating to engage out of fear of being judged
— Never sharing her insights or perspective publicly

Now, her strategy looks like this:

— Clear direction on the role she wanted
— Cohesive resume and LinkedIn throughline
— An engagement strategy that built real visibility
— Posting original content weekly to build authority

See the difference?

❌ Less guesswork
✅ More intentionality

But that's not all.

We got crazy specific about her LinkedIn content:

— The exact topics she wanted to align with
— The companies that should be paying attention
— The decision-makers she wanted reading her posts
— The exact message she wanted to communicate
— The clear value her expertise demonstrated

This works because your content shapes who pays attention and what happens next.

It's like a magnet.

Attract the right people and the right conversations, and it's just a matter of time before you get that offer.

Get it wrong though?

You're left wheel-spinning.

P.S. If you're feeling stuck and:

➝ struggle with focus challenges or overthinking
➝ have zero clarity on what you want to do next
➝ have a confusing resume and LinkedIn profile
➝ want a strategy that plays to your strengths

I'm opening up 4 more spots to work 1:1 with US-based senior leaders to help them do just that.

DM "Momentum" if you want to see how this works.

2025 David: What I got wrong (and what actually worked):

1. Every tough year means something is broken.
↳ Last year stretched me.
- It also sharpened the business.
- Some things worked. Others needed rebuilding.
- Both were true at the same time.

2. Growth required grinding harder each year.
↳ That belief aged poorly.
- Revenue stabilized when systems replaced urgency.
- Fewer calls, better containers, clearer expectations.
- Momentum came from consistency, not exhaustion.

3. More availability meant better service.
↳ Wrong math.
- Being always on blurred boundaries fast.
- The work improved when I protected my time.
- Clients got a calmer version of me. Family did too.

4. Recruiting expertise alone would be enough.
↳ Half true. Half naïve.
- I knew hiring systems inside out. 
- I underestimated the impact of identity loss.
- Execution followed once people felt steady again.

5. Transparency would land the same for everyone.
↳ That was projection.
- My ADHD diagnosis reshaped how I work and talk.
- I assumed everyone shared the same openness.
- Meeting people where they are built trust.

6. One unified workspace would solve everything.
↳ Spoiler: it didn’t.
- Persona worked for strategy and layered thinking.
- Content suffered when context got too crowded.
- Custom GPTs restored clients' voices fast.

7. More structure always equals more progress.
↳ I learned this one the uncomfortable way.
- Granular milestones worked for me.
- Clients experienced the same system as overload.
- Fewer steps created more follow-through.

Here’s what I know for sure:

☑ Clarity compounds faster than effort.
☑ Systems fail quietly before people do.
☑ Protecting your energy is part of the work.

Grateful for the clients who trusted me through the experiments and the resets.

2026 gets a cleaner version of everything.

P.S. What’s one shift from last year that stuck?

——
Hi, I’m David. I help high-performing leaders get clear on their next move and show up with confidence.

If time off didn’t shift the direction question, it probably wasn’t ever about energy.

I keep noticing this in the first week back. 

People get a bit of distance over the holidays. 

Quieter mornings. Fewer meetings. 

Just enough space to breathe and think that once the noise drops, things will probably feel clearer.

And then you make it to Friday.

You’ve been back in it long enough to tell what actually changed and what didn’t. 

The same career question’s still there. 
The same next role that isn’t quite defined. 
The same sense that the story still isn’t clear.

Even though you really hoped it might be by now.

Nothing really shifted. 

It’s not heavier, but it’s not lighter either.

From the hiring side, this is usually the part people don’t clock straight away.

It’s rarely about motivation, or effort, or a reset.

What lingers tends to be quieter than that. 

It’s the part where what’s next still feels fuzzy, where every option can still be justified. 

Where the story sounds fine in your head but wouldn’t quite land in a real conversation yet.

That’s the stuff a few days off doesn’t touch.

I don’t think that moment gets talked about much. 

That realization in the first week, when the calendar’s filling back up but the direction still hasn’t locked.

You’re left sitting with the same unanswered question you parked a couple of weeks ago.

It tends to just sit there for a bit, whether you’re ready to deal with it or not.

Some questions just take longer than a break.

The hardest roles to leave are the ones you're stuck explaining why you stayed.

I was sixteen years into a recruiting career. 

It wasn't bad, it just wasn't right anymore.

I remember this one Friday night, dinner done, sitting on the sofa half-watching Dexter, phone in my hand.

And there it was again, that question, the one I'd been carrying around for months but kept putting off because there was never a good time to deal with it.

I wasn't stressed or spinning, and to be honest, my week had been fine, which was the weird part.

When things are bad, you have a reason to move.

But when deals are closing, and big commission checks are rolling in, you start wondering why you're still thinking about leaving at all.

I sat there for a bit, finished my tea, and went to bed.

Woke up the next morning, same commute, same desk, same pipeline to work, and that question was right there with me like it had been the whole time.

I didn't do anything about it that week. 

Or the week after.

But it didn't go anywhere either.

P.S. Ever had one of those moments?

——
Hi, I'm David. I help high-performing leaders get clear on their next move and show up with confidence.

You don't need a perfect story to start a job search.

But most senior leaders act like they do.

That usually means:

- Waiting until the story feels "tight"
- Believing every chat has to go somewhere
- Pressure to sound confident before you feel clear

At senior levels, you're carrying identity, reputation, and expectations into every single conversation. 

That's a lot of weight. 

No wonder it feels exhausting.

Here's the reframe most leaders need:

A search is a private, low-pressure exploration phase.

The goal is just to gather information:

- What energizes you now
- What you don't want anymore
- What trade-offs you're willing to make

Clarity doesn't come 𝗯𝗲𝗳𝗼𝗿𝗲 you start.

It comes 𝗯𝗲𝗰𝗮𝘂𝘀𝗲 you start.

taplio

The Battle

Jessica Sweet, CPCC, CEIP, LICSW 🇺🇦

David Hannan

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The Battle

Jessica Sweet, CPCC, CEIP, LICSW 🇺🇦

David Hannan

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}David Hannan's LinkedIn Performance

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