Career Transitions & Reinvention

A client in her late fifties relocated across the country to care for aging parents, leaving behind a successful house-cleaning business she'd run for over a decade. She arrived certain she was unemployable in an office job: no recent office experience, no computer skills, no local connections.

My coaching elicited a different story. What was a typical Monday like at your old jobs? She'd processed payroll and led new-hire orientations. What software did you use? Word and spreadsheets, and she'd trained managers through a system upgrade. What did you handle with new hires? I-9s, compliance tracking, all of it. What was your volunteer work? Representing nursing home residents in front of judges as a certified mediator.

None of it had counted, in her own mind, as real experience, as it seemed too long ago. The question that actually moved her: what evidence do you have that you can't do this? She had none. Six weeks after relocating, she was hired as an HR Assistant at a skilled nursing facility. Nine months later, her hiring manager recruited her to a different organization in an HR Manager role, and she's working toward her PHR certification.

Twelve years as a project manager at a boutique marketing agency had worn a client down to the studs. Account executives promised clients things production couldn't realistically deliver, and he sat in the middle, absorbing it from both directions. Clients felt shortchanged. Production felt unappreciated. He conducted the same symphony of disappointment, on repeat, for everyone involved. He wanted out of marketing and project management entirely, and had no idea what to consider instead.

The engagement included assessments, values and strengths work, and a genuinely close look at what he actually enjoyed. The answer surprised him. He hadn't lost interest in marketing at all. What our work untangled was that agency operations themselves weren't a fit for him, promising what account executives wanted to hear, then living with the fallout when reality didn't match it. He wanted a consistent brand and voice to stand behind, and work that connected to something he actually cared about: animal welfare.

He pursued going in-house, landing in a marketing role at the headquarters of a national nonprofit. The pay took a modest hit, one he closed by starting his own LLC, doing contract projects for clients he got to choose.

Kevin had spent over twenty years running IT, largely solo, for a single-location hospital: hardware, network administration, vendor management, HIPAA compliance, disaster recovery, and the list goes on. The only person onsite who has to know everything. A move out of state for family reasons made that specific kind of role hard to find again, given how specialized IT roles have become. He knew he was ready for something different, but had no idea what.

We started from pure curiosity, deliberately uninformed by his past job titles. What did he actually enjoy on a daily basis, and why? Where had he found real satisfaction? He explored his interests further as I guided him through his results on the Strong Interest Inventory, a fantastic tool for identifying work for which you'd have a high probability of finding satisfaction. His exploration kept circling back to investigation, jobs that involve detective work. That led him to learn more about cybersecurity, a field largely built on trying to hack your own systems before, then building the case for how to mitigate the risk. He began networking with people who do this type of work, asked what they liked, hated, what the job market was like, and how to break in.

He started certification courses to test the theory. The harder problem was credibility: how do you land a role with no job title reflecting this field? It turned out that over two decades working in the hospital, he had already been working with info security, if somewhat informally. He'd just never named it as such. Once his experience was repackaged with intention and focus, he landed a security analyst role at a large technology conglomerate, and was later promoted internally to an architecture and engineering role within one of its spun-off business units.

I've built a highly effective method for this, not generic interview tips. Send me the job posting, the resume and cover letter you submitted for it, and the title or role of anyone you know will be part of the interview. I run those through a custom AI tool I built (personal info redacted, of course), which generates an in-depth interview guide tailored accordingly. We use it to run a real mock interview, with feedback throughout, so you're adjusting and improving in real time, rather than trying to assimilate all the feedback days later.

After our session, you'll have homework. Using the interview guide to build rich, specific answers, mined from your own track record. You probably won't get asked these exact questions in the real interview. That's not the point. You'll have already done the hard work of pulling your best stories out of memory, on your own time, instead of blanking out on finding them live, under pressure, while someone's watching you think.

Most interview prep fails at exactly that moment: knowing you have great examples, but not being able to reach them fast enough when it counts. My process gets you there before you ever walk in the room.

A client had just relocated to Houston, the partner of an expat whose career had brought them to a new city and country. Her resume was outstanding: Big Five consulting experience, real change leadership credentials, more executive presence than most people chasing a leadership role at a Fortune 100 company. She could interview well. The problem was what happened in her own head while she did it.

She doubted herself mid-answer, undersold what she'd actually accomplished, and over-explained the questions she felt least sure about, exactly the moments that needed the most confidence.

We worked on building tighter, more decisive answers to her trickiest questions, and on catching herself before the second-guessing took over.

She advanced to the final round for a change management leadership role at a global energy company, including a complex case study. I helped her prepare to deliver the presentation, and six weeks later, we met to toast her start date.