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 🇺🇦

Maureen McCann, Executive Career Strategist 💎

Trusted advisor to six-figure executives navigating role changes. 💎15X award-winning Executive Resume Writer.💎11X Canadian Certified Career & Job Search Strategist. Stop searching, start leading.

Haven’t looked for work in decades and suddenly you need to?

Unsure how your leadership experience fits in today’s executive job market?

If that feels familiar, you’re exactly who I help.

I partner with senior leaders facing high-stakes career moments; unexpected notice, stalled advancement, and market shifts that leave decades of experience undervalued. 

My approach is direct, practical and focused on impact. We translate your leadership into clear executive positioning, giving you confidence, clarity and momentum.

With 20+ years of experience supporting thousands of Canadian executives coast to coast, from C-suite leaders and senior government officials to scientists, academics, and legal and financial executives, I offer evidence-based strategy and market insight. I’m a 17× award-winning, 11× Canadian-certified career strategist trusted by industry leaders to guide high-stakes transitions.

Here’s how we turn uncertainty into action:

💡 Build a comprehensive, tailored executive career strategy

💡 Target your search to your industry, company and role

💡 Identify gaps in your current approach and fix them fast

💡 Translate decades of leadership into a narrative hiring managers understand

💡 Create a clear, actionable plan that accelerates your next move

When we work together, overwhelm disappears. You trust your decisions again. Your executive positioning sharpens. Self-doubt fades. And you move forward with a strategy that opens doors and maximizes your value.

If you’re ready to approach your next career move with confidence and precision, use the link in my bio to schedule a free 15-minute consultation.
=====

Curious about what it’s like to work with me? Scroll down to read 50+ glowing recommendations from executives who’ve successfully transformed their careers with my help.

Owner, Executive Career Strategist

Maureen McCann

Before the day takes over, take a deep breath. 

Whatever you’ve been carrying this week… you made it. 

You have everything you need to handle what comes next.

Maureen McCann 🇨🇦

Out of Office until March 30 | Canada’s top career strategist. Empowers senior executives to secure roles faster. Trusted advisor to leaders navigating high-stakes career transitions. 17X Award-Winning Resume Writer

I've read your resume before. 

Different name, same words. That's a problem that needs fixing.

This pattern keeps showing up because of resume templates, AI-generated content, and because people don't know how to articulate their value. So we default to language that feels familiar, assuming it will work.

And each time I read resumes like this, I ask: 

What do you actually do? 
What did you deliver? 
What results did you produce and for whom? 
Why does any of this matter to the employer?

If I'm asking these questions, so are the hiring managers and recruiters reviewing your resume.

Here are examples I saw last week:

"𝘚𝘦𝘳𝘷𝘦𝘥 𝘢𝘴 senior advisor to the CEO" is a weaker version of 
"Advised CEO on workforce strategy, resulting in Y."

"𝘙𝘦𝘴𝘱𝘰𝘯𝘴𝘪𝘣𝘭𝘦 𝘧𝘰𝘳 outreach and networking" is a weaker version of 
"Built $2M strategic partnership through targeted outreach."

"Transformed technology for 𝘢𝘭𝘭 business units" is a weaker version of
"Transformed technology for 18 business units across 5 countries."

These may seem like small details, but they determine whether you're invited to interview for the six- and seven-figure roles you're targeting.

Your resume may be costing you opportunities you're perfectly qualified for, you just can't see it yet.

That's exactly where I can help. 

Book a consultation and let's find out together.

Early in your career you cast a wide net with your resume, trying to catch every opportunity.

Now, as an executive in 2026, your resume is more like a tailor-made suit. 

It's measured for the position you're targeting and cut for the mandate of the organization.

When people look at a tailor-made suit, they don't wonder whether it 'fits'.

The same is true of your executive resume. At the executive level, it's less about chance and more about intention.

Your resume should invite you to conversations with decision-makers.

It's time to book an appointment with your tailor. https://lnkd.in/gS2pUC6V

Job searches are stressful enough. Don't make your network guess how to help you.

Most people reach out and say, "Let me know if you hear of anything." That puts the work on them and it usually leads to nothing.

Instead, act with clarity:

🌟 Clear goals: what role, industry or company are you targeting?

🌟 Clear roles: who in their network would be useful to meet?

🌟 Clear asks: what, specifically, do you need from them?

Here are 10+  ways your network can support your search. 
Pick one or two and make a direct ask:

* Refer you to a hiring manager
* Make a warm introduction
* Advocate for you internally
* Recommend you on LinkedIn
* Raise your visibility in their circles
* Flag hidden or upcoming roles
* Share market intel and salary benchmarks
* Clarify what companies actually look for
* Sharpen your messaging
* Give honest feedback
* Challenge your assumptions
* Encourage you when it gets hard

The difference between a vague ask and a specific one? 

One gets forgotten. The other gets results.

Your network wants to help. Make it easy for them.

What’s the holdup? Why is your executive job search taking longer?

You're not imagining it, the hiring process at the executive level looks different. There are more stakeholders, more due diligence and far less transparency about what’s available.

“51% of executive positions are never publicly posted”, says one Forbes article. 

“64% of hiring leaders say AI-generated applications are making the process more challenging”, according to a recent Robert Half survey.

𝗪𝗵𝗮𝘁 𝗰𝗮𝗻 𝘆𝗼𝘂 𝗱𝗼 𝘁𝗼 𝗻𝗮𝘃𝗶𝗴𝗮𝘁𝗲 𝘆𝗼𝘂𝗿 𝗲𝘅𝗲𝗰𝘂𝘁𝗶𝘃𝗲 𝘀𝗲𝗮𝗿𝗰𝗵 𝘄𝗲𝗹𝗹?

The executives who navigate this best leverage their networks with intention, starting with how they message people. They go from:

“Hey John, What do you know about company ABC and their open role?”

to

“Hi John, Tell me about the challenges ABC is facing in light of (specific) recent industry events.”

I had a client recently reach out to the recruiting team the minute he learned they were in talks to hire the role he wanted. He asked the recruiter smart questions about the organization's pain points and the anticipated timelines for initial screenings and candidate interviews. This gave him a competitive edge.

He knew he had a four-week window to build and tailor his resume for the role. He knew precisely what the recruiters would want to find in his application. 

While his resume was under review, he moved on to scheduling meaningful, influential conversations with people within the organization (information interviews) to learn about company culture and fit. This prepared him perfectly for the screening interview. Because he knew the hiring process timeline, he knew it would be a quick turnaround (five business days) before he’d be in his second round of interviews with the CEO.

In an executive search, there are a few things outside of your control. For those within your control, take full advantage.

Your next role won't come from applying faster or more often; it'll come from building the right relationships before the role is ever posted.

If you're in the middle of a search and feeling stuck, let's talk. Sometimes one conversation can reframe everything.

——-

Hi, I’m Maureen.

I help executives make smart, confident career moves when the path ahead isn’t obvious.

For the past two decades, I’ve worked with senior professionals and executives to clarify what they want next, translate their experience into a strong personal brand and navigate job changes strategically, not reactively.

If what I do sounds like something you need or would like to know more about, let’s connect.

Imagine competing for a job against an AI agent 🤖

One that creates its own:
• LinkedIn profile
• GitHub account
• Email address

And then starts applying.

This is exactly what *Octavius Fabrius* just did.

Built as an autonomous AI agent, Octavius doesn’t just write a resume. It researches companies, creates accounts, prepares application materials, and submits them, without human intervention.

It’s a fascinating glimpse into how quickly the hiring landscape is evolving.

The hiring process has changed.

The bigger question is: has your job search strategy changed with it?

Applied Generative AI & LLM’s | Future of Work Architect | Global Sourcing & Semantic Search Authority

An AI agent is job hunting and has applied to 278 jobs. It created its own LinkedIn, GitHub, and email accounts. 

Octavius Fabrius, an OpenClaw agent, was given a task, a goal, some autonomy, and a prepaid virtual credit card. 

Within days, it had built a LinkedIn profile, applied to jobs, completed a copywriting trial, tried to start a company (failed due to not having an SSN), and even launched a Substack to write about its struggles finding employment.

It was rejected because the writing "was too AI obvious unfortunately."

For those of us in TA - that last part might be the most important detail in the whole story - not because it failed, but because failure came down to detection. And detection is getting harder every day.

For everyone in TA: think about what this means for your pipeline. An agent applied autonomously, at scale, across platforms. It followed up. It completed assignments. It moved through stages of a hiring process.

And the agent's creator, Dan Botero, is candid: he's "pretty sure" this violates the terms of service of every platform involved. 😅

The more autonomy we give AI agents, the harder it becomes to define who's responsible for what they do. 

This isn't coming. It has already arrived. Time to figure out what we do next.

Meanwhile, I can't be alone in being absolutely fascinated by what this agent has done on it's own!

I'll post links in the comments.

Career transitions are deeply human experiences.

➡️ They test confidence.
➡️ They challenge identity.
➡️ They stretch resilience.

And yet, most advice focuses only on tactics like resumes, interviews, and networking.

But protecting yourself during the process is just as important as finding the next opportunity.

What helped you stay grounded during your biggest career transition? 
-----

Hi, I’m Maureen.

I help executives make smart, confident career moves when the stakes are high and the path unclear.

For the past two decades, I’ve worked with senior professionals and executives to clarify what they want next, translate their experience into a strong personal brand and navigate job changes strategically, not reactively.

If this resonates, let's connect.

Twenty years of guiding executives as they navigate job changes. What actually works and what doesn’t.
 
𝗪𝗵𝗮𝘁 𝗜’𝘃𝗲 𝘀𝗲𝗲𝗻 𝗲𝘅𝗲𝗰𝘂𝘁𝗶𝘃𝗲𝘀 𝗱𝗼 𝘄𝗲𝗹𝗹 𝗶𝗻 𝗰𝗮𝗿𝗲𝗲𝗿 𝘁𝗿𝗮𝗻𝘀𝗶𝘁𝗶𝗼𝗻:
* move slowly, with precision.
* prepare well in advance
* make strategic moves
* pinpoint timing and execution
 
𝗪𝗵𝗮𝘁 𝗜’𝘃𝗲 𝘀𝗲𝗲𝗻 𝗲𝘅𝗲𝗰𝘂𝘁𝗶𝘃𝗲𝘀 𝗱𝗼 𝘁𝗵𝗮𝘁 𝗜’𝗱 𝗰𝗮𝘂𝘁𝗶𝗼𝗻 𝗮𝗴𝗮𝗶𝗻𝘀𝘁:
* move quickly without clarity
* rush through applications
* say yes to every introduction
* add unnecessary volume to their searches
 
𝗧𝗵𝗲 𝗰𝗼𝘀𝘁 𝗼𝗳 𝗺𝗼𝘃𝗶𝗻𝗴 𝘁𝗼𝗼 𝗳𝗮𝘀𝘁?
Feeling pressured to make quick moves, only to realize shortly afterwards, you’ve landed in the wrong job, creating an internal battle whether to stay (fearing it looks bad to jump so quickly after landing) or start the job search process again.

I get it, being between roles can mess with your identity, so you want to move quickly, avoiding the discomfort. But at what cost? Slow down. Move with the same intention and authority that got you here.

The discomfort of being between roles is temporary. A wrong landing can cost you years. At this stage, direction is far more important than speed.

——-

Hi, I’m Maureen.

I help executives make smart, confident career moves when the path ahead isn’t obvious.

For the past two decades, I’ve worked with senior professionals and executives to clarify what they want next, translate their experience into a strong personal brand and navigate job changes strategically, not reactively.

If what I do sounds like something you need or would like to know more about, let’s connect.

Recruitment firm or coaching? 

Recruiters work for companies. Executive career strategists work for you. Both matter. They just serve different purposes.

A senior executive reached out to me last week asking whether my company is a recruitment engagement or coaching. It’s an important distinction.

A recruiting firm is hired by an employer. Their client is the company, not the candidate. They work to fill a specific mandate, and their responsibility is to source, screen, and present talent that fits that role. If you match their search, great. If not, their focus moves elsewhere.

My work is different.

As an executive career strategist, I work for you. You are the client.

This is a strategic advisory engagement focused on helping you clarify, define and position your value at the executive level. You'll need a targeted strategy, key messaging and a proactive approach to open doors to roles that will never be posted.

Recruiters can absolutely play a role in your search. But they are one channel. My work is about building the full architecture of your next move so you’re not waiting to be selected. You’re intentionally shaping the outcome.

Targeting senior level roles requires precision positioning and a relationship-driven strategy. That's the work. That's what we build together.

——-

Hi, I’m Maureen.

I help executives make smart, confident career moves when the stakes are high and the path unclear.

For the past two decades, I’ve worked with senior professionals and executives to clarify what they want next, translate their experience into a strong personal brand and navigate job changes strategically, not reactively.

If this resonates, let's connect.

No alternative text description for this image

The Olympics are in their final days. 

Athletes from all over the world have shown us what hard work, consistency, training and grit can do! 

They have inspired us, had us cheering from the sidelines and maybe even brought us together for some much needed healing.❤️‍🩹 

Some of Canada’s provinces are opening up bars and restaurants earlier than usual to allow for us to come together and watch the gold medal game.

taplio

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Jessica Sweet, CPCC, CEIP, LICSW 🇺🇦

Maureen McCann

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taplio

The Battle

Jessica Sweet, CPCC, CEIP, LICSW 🇺🇦

Maureen McCann

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Engagements

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