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

10 harsh truths I learned switching careers at 50.

Thinking about a pivot? Read this twice:

1️⃣ You're not too old to change.
But you are too old to keep pretending you're fine

2️⃣ Purpose doesn't just appear.
You create it through messy action and alignment

3️⃣ Confidence won't lead the way.
But it will follow consistency.

4️⃣ Long careers makes choosing difficult.
Each option looks like the right and the wrong one.

5️⃣ Your old career isn't wasted.
It's raw material for your next chapter.

6️⃣ Focus won't magically show up.
You have to build systems that hold you together.

7️⃣ Motivation lies.
You need momentum, even tiny steps count.

8️⃣ You won't feel clear before you start.
Clarity comes after commitment, not before.

9️⃣ Reinventing yourself takes guts.
Especially when it’s easier to stay put than moving. 

1️⃣0️⃣ Progress will feel invisible.
Until one day, you realize how far you've come.

I learned these the hard way by breaking patterns I didn't even know I had. 

If I knew them sooner?

I would've spent less time overthinking and more time trusting the process.

Which one feels the most true for you?

Share below in the comments—let's compare notes.

10 surprising job search truths I know at 53.

(that I wish I knew at 33)

1. Networking is essential.

Realize that building authentic relationships can open more doors than just handing out business cards.

2. Building a personal brand is crucial.

How you present yourself online and offline can make or break opportunities in your industry.

3. The myth of job security. 

Recognize that the concept of lifetime employment is largely outdated. Diversifying your skill set and being adaptable are your best insurance policies.

4. Self-care is a priority. 

Prioritizing self-care can enhance both your job satisfaction and performance. Ignoring this can lead to burnout and reduced productivity.

5. The value of cultural fit. 

While high salaries or brand-name companies may seem attractive, finding a workplace where you fit in culturally can be equally, if not more, important.

6. Facing ageism. 

Discrimination based on age is a real challenge; staying relevant and adaptable are keys to overcoming it.

7. The importance of time management. 

Understand that being busy isn't the same as being productive. Effective time management is a crucial skill for a fulfilling career.

8. The power of negotiation. 

Whether it's your salary, role, or benefits, strong negotiation skills can significantly impact your path.

9. More than just job titles. 

There's more to job satisfaction than just your title. It's about work-life balance, company culture, and a sense of purpose.

10. Financial planning is a necessity. 

Planning for financial stability is essential, whether for retirement or navigating potential job losses.

The only thing I'd change? 

Start believing them sooner.

PS. What would your #11 be?

10 Job Search Truths I Learned the Hard Way

Last week a client said, "I could do any of these five things."

That's where most people get stuck.

I've been sitting with a lot of people whose background just makes sense. 

They've got the experience, and they've done some pretty cool things, but then you ask them what they want next, and there's this shift.

They can talk for twenty minutes about what they've done. 

But when you ask, "So what's the next move?" something happens. It's like they suddenly realize they're choosing which version of themselves to lead with. 

Not which job, but which identity.

One version is the operations person. The systems builder. Another is the people leader. Hired well and trained people up. And then there's the strategist. The one in the room where decisions got made.

They're all real, and they've all got proof.

But when they try to hold onto all of them, their voice changes. There's this hesitation. 

I'll hear it when they talk about what they want next. They'll start clear and then it softens. "Or I could also..." shows up mid-sentence.

It's not a confidence thing because they know they're capable. It's just that their story doesn't actually point anywhere. It sits there in all directions at once.

A hiring manager can hear that. 

They hear the capability, the experience, but they don't hear where the person is actually trying to go.

It's not that any one version is weak, they just haven't decided which version is actually driving the ship yet.

So everything stays flexible, and everything stays technically true.

And why they're stuck between all five.

PS. The first in your list is usually the one.

Defending my team didn’t rattle me, the train ride home did.

This was 2018, back when I was still recruiting.

I had to push back on senior leadership about something that would have landed badly on my team. 

In the room, I kept it together. I listened, took notes, tried not to react. They said I handled it well.

But on the Metro-North ride home, I felt completely detached, just staring out the window. 

I got home and shut down, and the next couple of days took more out of me than I thought.

When you’re the one carrying the weight in the room, you don’t really get to fall apart.

You regulate yourself, you absorb what’s coming at you, and you try to make it usable for everyone else.

That’s how you end up in bigger rooms.

It also takes something out of you.

Before that meeting, I’d already rehearsed what I was going to say and run the objections in my head. 

While I was sitting there, I wanted out, but I kept it together because that was the job.

None of that shows up on a resume or in a performance review.

When I talk to senior leaders now who are between roles or thinking about their next move, this is usually the part that doesn’t come up.

They’ve been carrying that weight for years, and it just feels normal.

The calm exterior, and underneath it, a steady internal burn rate.

You don’t really notice it while you’re still in it.

Sometimes in a career transition, the exhaustion’s been building long before the search even starts.

P.S. What other parts of leadership don’t get airtime?

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Jessica Sweet, CPCC, CEIP, LICSW 🇺🇦

David Hannan

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The Battle

Jessica Sweet, CPCC, CEIP, LICSW 🇺🇦

David Hannan

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