Portland,
Oregon.
The original outpost. Where the Long Game was built from scratch—and where the full playbook lives.
“We built this in Portland because Portland doesn’t give trophies for showing up.”
Long Game started as a solo operation out of Portland, Oregon—one coach, one city, one relentless belief that career development doesn’t have to be transactional. Coach Leighty built the methodology here: part sports science, part organizational psychology, part earned field knowledge from Adobe, Cisco, and Nike.
Portland is still the lab. Every new program, every framework, every piece of content gets stress-tested here before it goes out to the network. The HQ basecamp runs the full suite—individual coaching, group conditioning, the Ranger Station community, season-ticket packages, and the Trailhead youth track. If it exists in Long Game, you can get it in Portland.
The city earns it. Portland’s career landscape is legitimately difficult—tech layoffs, nonprofit funding gaps, hybrid-remote friction, and a startup scene that’s rebuilding after a rough stretch. That’s not a liability for the Long Game. That’s the terrain we were built for.
How we got here
Programs at HQ
1-on-1 Coaching
Direct access to Coach Leighty. Strategy, accountability, and execution on your career goals—at the pace your situation requires.
Conditioning
Cohort-based career conditioning. Build the fundamentals alongside other driven professionals in a structured monthly program.
Ranger Station
The Long Game community hub. Resources, peer support, live events, and direct access to the full network—all in one place.
What’s open today
Career landscape
Portland’s economy sits at a complicated crossroads: a mid-tier tech hub trying to hold its ground after major layoffs, a nonprofit sector under sustained funding pressure, and a creative/agency ecosystem that’s leaner than it was five years ago. That means the professionals here are dealing with real career complexity—not theoretical.
Post-layoff rebuilding
Intel, Nike, Adidas, and regional tech shops have all restructured. Many strong professionals are repositioning or going independent. High coaching demand, complex narratives to manage.
Funding-driven volatility
Oregon’s nonprofit sector is large and historically stable but under pressure from federal and state funding shifts. Lots of mid-career pivots incoming.
Structural contraction
Portland’s agency scene has contracted. Freelancers and displaced creatives need help reframing and finding leverage in new markets.
Hidden strength
Portland is an underrated ops hub—warehousing, distribution, and logistics talent is strong here. Undercoached, high opportunity.
What’s available
1-on-1 Coaching
Individual Coaching
Monthly coaching engagement. Full strategy, accountability, and direct access to Coach Leighty on your schedule.
Intro Call
Free 30-minute conversation. No pitch, no pressure. Just a real look at where you are and whether Long Game is the right fit.
Resume + LinkedIn Audit
Deep-dive review of your materials. Specific, written feedback on what’s working, what isn’t, and what to fix first.
Career Strategy Session
90-minute working session on your career strategy. Walk in with a problem, leave with a plan.
Conditioning
Monthly Conditioning
Cohort-based career conditioning. Foundations, drills, and accountability in a structured group format. Month-to-month enrollment.
Full Season Camp
Multi-month structured conditioning program for professionals ready to go all-in on a full-season build.
Ranger Station
Ranger Station Access
Monthly membership to the Long Game community. Resources, live sessions, peer network, and direct line to the coaching team.
Season Ticket Package
Prepaid session block for high-frequency players. Best per-session value for committed clients.
Trailhead (Youth)
Trailhead Program
Career and life-skills development for young adults. Parent-led enrollment. Builds the foundation before the big decisions hit.
Pricing at a glance
Individual Coaching
Full monthly engagement. Includes strategy sessions, accountability check-ins, and direct access to Coach Leighty between sessions.
From $350/monthConditioning
Monthly cohort enrollment. Career conditioning fundamentals in a structured group format. Renews month-to-month—no auto-billing.
From $125/monthRanger Station
Monthly community membership. Live sessions, resources, peer network, and coaching team access. Waitlist currently open.
From $45/monthSession Bundle
Prepaid block of sessions. Best per-session value for committed clients who want to move fast and work in depth.
From $600/blockYour long game
starts in Portland.
The HQ basecamp is open. Book a free intro call and find out if Long Game is the right fit—no pitch, no pressure, no obligation.
Local favorites
Coava Coffee
High ceilings, serious beans, and a space that actually earns the focus you need. The Grand Ave location is the working-session standard.
Grand Ave location preferredForest Park
30-mile trail system inside city limits. Wildwood Trail to Pittock Mansion is the go-to—enough climb to earn the views, enough canopy to stay sane.
Wildwood Trail → Pittock MansionLuce
Northeast Portland neighborhood Italian. The kind of place you go when the work is done and you want a real meal without the production.
NE PortlandPowell’s Books
The obvious one, but obvious for a reason. You can lose an afternoon in the business and career section and walk out with three books that change your thinking.
Burnside flagshipCouncil Crest Park
360-degree views of the city, Hood, Adams, Rainier, and St. Helens on a clear day. Walk up when you need perspective—literal or otherwise.
SW Portland hilltopNext Adventure
Portland’s real outdoor gear shop. Good surplus section, knowledgeable staff, and the right gear at prices that don’t require a finance plan.
SE PortlandPortland, OR
Coaching sessions available in-person and remote. Book at longgame.setmore.com.