The Umbrellas We Never Used (A Cabo Trip, a Birthday Bash, and a Reminder About What Really Matters) Sometimes you don’t realize how much you need a break until you take one. For years, I’d talked about going to Cabo San Lucas — not for beaches or golf, but for one specific thing: Sammy Hagar’s birthday bash. The tickets are like gold dust — a hundred thousand people chasing three thousand seats. You have to win a lottery just to buy  one, but somehow, this year, we got lucky. We looked at each other and said, “The timing isn’t great… but let’s go anyway.” There was a lot going on. My official retirement was days away, there were birthdays galore that week — my mom’s, my father-in-law’s, my dad’s. Everything felt urgent, everything was a priority. But we decided to set it all aside. After all, Sammy wasn’t getting any younger — and neither was I. Life wasn’t going to stop spinning just because we stayed home. So, we booked our flights, grabbed a hotel on the marina, packed our bags, and headed to Cabo. The First Steps We did what any seasoned travelers do: watched a few YouTube videos first. Getting from the airport to the hotel looked expensive, but the city bus seemed easy — $8 per person instead of $40–$100. City bus it was! Finding the stop was easy enough, once we pushed through the gauntlet of timeshare salespeople who pounce the second you clear customs. Finding the right bus — easy. Paying and getting a seat — easy. Understanding the route — complete mystery. There seemed  to be bus stops, but you could also just wave and it would pull over. No announcements, no signs, no clue. So of course, we missed our stop. A beautiful 96° day. Ninety percent humidity. Three kilometers of walking. Did I mention the sun? The heat? The humidity? Oh — and packing luggage through rush hour traffic. The joys of travel. By the time we finally reached the hotel, sweaty and half-delirious, we were greeted by air conditioning, the smell of salt, and that view: the marina glittering under the afternoon sun. We fell into Cabo’s rhythm almost instantly. The Rhythm we fell into Every morning we’d walk the waterfront — sea lions barking, waves crashing, the breeze off the Sea of Cortez and the mighty Pacific. Then coffee on the veranda — those long, quiet breakfasts you never get at home. We’d wander with no plan, just curiosity. Sure, we did the tourist things: a boat ride to El Arco, a dinner cruise, strolling through art gardens and market streets. But most days we just explored side roads and back alleys, found a shady spot for a drink, and talked with people from all over the world. It wasn’t about sightseeing or souvenirs. It was about breathing again. Slow, deep breaths that rinse the stress away and refill the soul. The Birthday Bash The reason for the trip finally arrived — the show. It was everything I’d hoped for: good music, a calm crowd, the songs that carried us through our youth. The audience was older, a little slower, but still alive. No drama, no chaos — just smiles, laughter, and that electric moment when a band you grew up with reminds you who you used to be. For one night, the years folded in on themselves, and we were young again. Happy birthday, Sammy. The Rain That Stopped the World, or slowed down Cabo anyway Then came the rain. Not much by our standards, but for Cabo — it was big news. Locals were talking, shops boarding up, people rushing to finish errands before the storm. Back home, this would’ve been a summer drizzle. In Cabo, it was an event. The city gets 300 days of sunshine. Most locals don’t even own umbrellas — because why would they? When it rains, they stay home, eat, laugh, enjoy the break from the sun. Shops close. Streets empty. Families just wait it out together. We, on the other hand, went into full mission mode. Find umbrellas we must! Walmart? No. Costco? No. Not a single store carried them. The only umbrellas in town were for the beach. Finally, tucked in a dusty corner of a mall, we found a tiny shop selling a few forgotten umbrellas for $14 each — practically collector’s items. I grumbled, bought two, and walked back to the hotel feeling victorious. Later, while sitting drinking my victory cerveza, the waiter looked curiously at the umbrellas sitting on the table, I told our waiter the story, the saga it was, the miles walked, how many people we talked to in an effort to track them down. He laughed and said he’d owned only one umbrella — years ago, when he’d studied abroad in Nebraska. We talked about how strange Nebraska had been to him — green, flat, wet. How much he’d loved it, and the people. Then he smiled and said, “When I came home, I left the umbrella there. I knew I wouldn’t need it again.” That line stuck with me. For him, the rain wasn’t something to fight, not just an annoyance to deal with — it was a reason to step back and breath, stay home with family, a part of life that meant something different here. And in that, there was a kind of peace we forget exists. Contrast and Gratitude We also took time and wandered beyond the postcard Cabo — we made our way out beyond the tourist zone — out where the shiny hotels fade, beyond the gated residences of the Hollywood elite, sports figures, and other wealthy part time residents, out to working class neighborhoods where the real Cabo begins. People hustled, worked hard, smiled big. Kids played in the streets, and in dusty parks. Houses were small, modest, some unfinished, sometimes patched together — but the laughter was full, the spirit was bright everywhere we went. Out here we saw tiny places to grab food, or drinks. Sometimes nothing more than a couple tables on the sidewalk in front of what appeared to be someone's home, but still the smiles were there, big genuine, welcoming. We prayed for those families, for safety, for opportunity. But more than anything, we felt gratitude — the kind we too often misplace in our busy lives. We talked about the disparity that exists in a place like this, a place full of haves and have nots. These weren’t people chasing more; they were living with what they had. And it looked a lot like contentment. It humbled us. Made me think "maybe they should be praying for us" — to remember what really matters. The Umbrellas We Never Used By the last day, our umbrellas sat untouched on the hotel dresser. It rained lightly that morning. We sat beneath a canopy, sipping cinnamon coffee, listening to drops roll off the edges, holding hands while sea lions barked somewhere out in the mist. And I thought — how much noise we fill our lives with. How many moments of together  we trade for motion or money. How much of what is truly irreplaceable we so easily trade for what we think is valuable at the moment. We’d walked miles for something we thought we needed, only to discover what we really needed was to stop walking. To just be. Coming Home We came home recharged, grateful, and quiet. Not the quiet of fatigue — the quiet of realization. Life doesn’t pause for anyone. But if you’re lucky enough to step away — to listen to the rain, to wonder what sea lions talk about, to hold hands and watch the world slow down — you come back seeing your own world a little clearer. The umbrellas? Still in the bag. A reminder not of what we thought we needed to endure the rain in our life. But of what we truly need: peace, presence, and gratitude for a little rain that makes you stop and listen to the rhythm of life. Keep up with what is next here: Fedtofreedom.org If this resonated with you, hit follow and sign up so you’ll get the next post. Consider buying a coffee to help support the site. And reach out if you want help with resumes, research, or sharpening your interview skills.

Plan Your Career Around Your Life (Before It Plans Life For You) The old adage:   to fail to plan is to plan to fail —it’s true in careers, too. Careers are tricky. Too many people chase the next paycheck or promotion without asking the most important questions: Where do I want my life to be? What do I want it to be? This post is for folks early in their careers. If you just need a job , there’s still value here—but I’m talking to people who want a path  that aligns with their skills, values, and long-term goals. Before you polish a résumé or sprint after job postings, stop and ask: Where am I willing to work, and what am I really working for? If you don’t answer that honestly, you’ll spend months in a scattershot hunt—landing roles that fill a bank account but drain the soul. Here’s the truth: if you don’t plan your career around your life, your career will plan your life for you.  And usually not in a way that leaves you happy. That’s how the golden handcuffs  get locked on. Once life reaches the point where you must  have this job and must  have that income (diapers are expensive), leaving gets tough. You can wake up bitter, stuck, and wondering how you got there. Start With Life, Not Work When I coach, where we start depends on stage and need. But the basics don’t change: Location, mission, lifestyle. If you’re not willing to move, say so. If you want to be close to family, own it. If the mission matters more than money, (or the other way around) be clear. Career vs. paycheck. If all you want is a paycheck, fine—just don’t pretend it’s a planned path. I want to stop for just a second. Yes, many a person has just taken a job with a company, that turned into a career. If that happens be grateful. But over the last four decades even those people that ended up there, have said to me, "this is not where I thought I would be." Be deliberate: Does this job move me closer to where I want to be in five years? Trade-offs. You can’t have it all—salary, mission, location, growth—at the same time. Rank them. Decide what you’ll flex on and what’s non-negotiable right now . Priorities shift. Maybe you’ll put growth above all else early on willing to move every two years and chase the next big challenge. Later, location or stability might climb to the top. Maybe you’re willing to pay $3,600/month in Silicon Valley and live on ramen for two years because the experience will set you up to start your own business back home later. That’s a choice—make it consciously. Manage the Career You Start Oh, you thought it was “get it started and it’ll all work out?” Nope. You’re usually one corporate buyout away from starting over. (Yes, I have been there.) This is where being deliberate  about your plan and vigilant  about the market intersect. If the market is demanding skill X  now, and your job keeps you locked on skill Y  with no path to cross over, you need to re-evaluate. COBOL programmers  were once the backbone of banking and government systems—now it’s a niche. Some still do well, but most watched demand fall as newer languages took over. Flash developers  were red-hot in the 2000s—then support died and mastery of an “essential” skill became useless almost overnight. Point:  staying still is sliding backward. Keep your skills moving where the market is headed, not just where you’re comfortable. Be honest about how much time you’ll give any employer to get where you truly want to be. Be just as honest about when it’s time to move on. Priorities will change—plan for it. The Five-Year Bites A mentee told me, “Sir, I have no idea where to start.” I said: “Write your life in five-year bites—and no work/career talk.”   Make simple qualifier statements. Let the life you want to live shine a light on the career you need to plan. At 25 I want… At 30 I want… At 35 I want… At 40 I want… He came back with: 25: travel and see some of the world 30: know where I want to live 35: married with kids, own a home etc. No career talk. Just life. Then we worked backward: Where will that family live? What kind of place? What kind of stability? If you want that at 35, maybe you grind it out in a one-bedroom in a city you don’t love at 25—traveling, figuring out where feels like home, and building the skills that get you where you want to be at 30. That’s planning: Tie career steps to being the vehicle for life steps.   We worked this for a few months. He’d bring ideas; I’d ask, “Did you think about this?” I made it clear: Plans aren’t etched in stone. Life changes. You might plan to be somewhere for a few years and—boom—love shows up. That doesn’t derail everything; it means you step back, run the process again, and re-evaluate. Trade-Offs Are Real (Again) You can’t have salary, mission, location, and growth all at once . Rank them. Decide what’s non-negotiable and what you’ll flex on—and for how long. Maybe you take less pay for mission now, then shift later for family stability. That’s okay.  Know it. Plan it. Move intentionally. The Lesson That intern? He took a stretch role in Columbus he wasn’t thrilled about after he graduated. Learned a lot over the next few years. Then Detroit for two years—more growth, plus classes to fill skill gaps that became obvious in the work. Then he landed the job  outside Chicago—right where he wanted to be, just past 30. Bought a townhouse. Got promoted a couple of times. Met a schoolteacher at dance class. Married at 33 (ahead of plan—because love). When kid #3 was on the way, they sold the townhouse and bought in the suburbs. Today: three kids, director-level career. He still reaches out sometimes to say thanks—and admits he plagiarizes my stuff in his own mentoring program. Not because I told him which job to take. We talked about almost everything except  jobs. He learned to plan his career to support the life he wanted to live. “We talked recently; now they’re in the thick of post-career planning.” After all, once your career is done, life is still there—and it won’t wait for you. If you’re early in your career, don’t just grab what’s easy. Think five years ahead. Write it down. Map it. Make the job serve your life, not the other way around. If this resonated with you, hit follow and sign up so you’ll get the next post. Consider buying a coffee to help support the site. And reach out if you want help with resumes, research, or sharpening your interview skills.

The Day’s Campaign Report Some days just come at you sideways, and all you can do is roll with it. Today was one of those days. I woke up ready to take advantage of the weather, get some yard work done, maybe clean out the garage a bit — hoping I’d earn a trip to the driving range or at least a cold beer outside. Not in the cards. But the day turned out memorable all the same. Phase I: Dawn Patrol Glen up, straight into 100 crunches, coffee down, choppers brushed and cared for. Short jaunt down the highway to the Indian Head Rail Trail for a 16.2-mile bike ride. Outbound was a glide, a slight downslope, but inbound was the grind — every bit of that slope coming back at me. I did manage to shave five minutes off my last sortie, which is progress I can feel. The trail itself was perfect: sunshine on my shoulders, a cool breeze in my face, deer grazing along the edge, birds chirping, people out, but not crowded. One of those mornings that makes you glad you got up early and makes you wish everyday could be this nice out. Phase II: The Unexpected Encounter Back at the parking lot, I walked into a parking lot etiquette situation I hadn’t trained for. Let’s just say it involved a surprise wardrobe malfunction at close range. Details? Classified — different platform required for dissemination. Tactical response: quick humor was attempted , situation awkward but seemingly diffused. Morale impact: high . Phase III: Mechanical Engagement Halfway through mowing the 3 acres, the Craftsman declared itself non-mission capable. The pulley stud had cracked and let the belt fly. Annoyance level: critical. A tactical retreat to the garage for reinforcements of the high caliber tool type to aid in my reconnaissance as to the full scope of the failure. After some hand-to-hand combat, with some bruised knuckles incurred, the enemy combatant was identified: one fatigued stud bolt, displaced and mocking me. It took grinding, cutting, and a resupply run to the hardware store before I could mount the counterattack. The repair was decisive. A Grade 8 phosphate-coated stud went in, backed by stainless washers and a nylon lock nut. That part isn’t failing again. While I had it apart, I replaced the belt, re-aligned the deck, and hit everything with lube. Might as well. The Craftsman roared back to life, mission-capable once more. Phase IV: Territorial Sweep The last acre and a half fell quickly to the Craftsman after that. A final sweep with a weed eater, and the backyard was secured, fences and trees cleared. The garage even gave up some ground — only a partial victory, but the first volley in what will be a longer campaign for garage supremacy. Campaign Outcome Mission success: Territory restored. Fitness gains logged. Morale elevated. Sometimes all you can do is laugh and make the best out of the day you’re given — and be grateful you were given a day at all. If you found yourself smiling, nodding, or remembering your own first ride, hit follow and sign up so you’ll get the next post. Consider buying a coffee to help support the site. And reach out if you want help with resumes, research, or sharpening your interview skills. Because whether it’s bowling balls or bicycle chains, the journey is always better when we keep rolling along together.

Let’s be honest — most cover letters put hiring managers to sleep. “I am writing to express my interest…” blah blah blah. If your letter reads like that, you’re already in the discard pile. ✍️ A good cover letter doesn’t rehash your entire resume. It connects the dots between you   and their problem . Think of it as your 30-second elevator pitch in written form. ⚠️ I want to caveat something here: This post is aimed at that early to mid-career professional. Or even a recent college graduate. It may not be applicable to someone just looking for that first job that will often be in a high turnover industry. Or for executive positions, which will be covered in a future posting. 🔎 There Are Two Main Types of Cover Letters In my experience there are two types that I have seen. The cover letter attached with a resume in response to a job announcement. The cold call letter that is sent unsolicited with a resume. ⚠️ "Cold calling with a generic cover letter and resume may feel like blasting a shotgun. Don’t do that."   ✍️ If you have marketable skills, education, and training, you should take the time to focus on quality outreach, not quantity. Focused time will almost always net you a position that you want, not just any job where they need a body now. 🔎 Why Cover Letters Still Matter Yes, some managers barely glance at them. Others read them after shortlisting resumes. Either way, a cover letter is a chance at bat. Done well, it tips the scales in your favor. Done poorly, it just wastes space. 💡 Pro Tip: From a hiring manager perspective, I would give a cover letter about 5 seconds worth of time. Unless it immediately struck me and kept me reading, I was moving on. ⚠️ When I say struck me, "I mean, I saw something quickly that made me want to look deeper into the resume". Normally that was a fact, or skill that I was looking for and I could see it immediately. 🔎 The #1 Mistake ⚠️ Generic, one-size-fits-all letters. “Dear Sir/Madam, I would like to apply…” "I am seeking a position that". That’s not a cover letter, that’s spam. If I can swap a company name with any other company, you’ve missed the mark. 💡 Pro Tip: Think of this as your first introduction, that first, handshake, that "tell me about you moment" (in 5 seconds or less). 🔎 Who Do You Address It To? “Dear Hiring Manager” Screams copy-paste . " To Whom it may concern": is "in my opinion" a nonstarter, period! A little digging goes a long way: Read the announcement carefully.  Often the point of contact (POC) is buried in the job posting. (If you reach out, they may not know a name, but they may know some details that will put you into a path to finding out) Google the company. The structure/org charts may lead you to a name, a contact, or at least the office, or team you would be working for. 💡 Pro Tip: You should already be doing this just to ensure you are targeting your resume correctly and understanding what experiences you have, that align with what this company needs. True for both your resume build and prepping for interview questions. Check LinkedIn.  Search the agency or company + job title. Often the team lead is right there. (Using the team, or department name shows you at least did some research) Call HR.  A quick call asking, “Who should I address my application to?” takes 30 seconds and shows initiative. Last resort.  If you truly  can’t find a name, or even the name of the team or department that has the opening, then “Dear Hiring Manager” works — but make it the exception, not the rule. 💡 Pro Tip: Addressing it to a real person instantly lifts you out of the “generic” pile. It shows you did your homework. ⚠️ (I can say from experience, out of thousands of resumes received over the decades. I can count on one hand the times I received a cover letter addressed to me personally as a hiring manager. Yes, I read those) 🔎 A Structure That Works Three short paragraphs (Or less) . That’s it. The Hook : Show why you want this  job. “As someone who has led federal acquisition teams for over a decade, I was excited to see DHS’s posting for a Program Manager. This is exactly where my background fits.” The Value Match : Connect your skills to their   need. “In my last role, I managed a $2B acquisition portfolio and built the process playbook now used across multiple agencies. I’d bring the same discipline and results to your team.” The Close : Tell them what you want. “I’d welcome the chance to discuss how I can help deliver results for DHS. Thank you for your time and consideration.” 🔎 Tailor Without Rewriting from Scratch Each Time! ✍️ Don’t reinvent the wheel for every job. Build a framework letter  with blanks you can fill in: ⚠️ (We have covered much of this in previous posts: "Interview like a pro", "Narratives vs Bullets", "Questions you will always be asked"). This is about building out your story and having it at the ready. Company/agency name. Job title. Space for 1–2 specific examples that align with the posting. Ending and signature block. ✍️ Swap those out, and you’re tailored in under 15 minutes. 🔎⚠️ Common Pitfalls Rehashing your resume.  If you’re just copying bullets, why send it? Too formal.  Nobody talks like a 19th-century butler. Too casual.  This isn’t a text message. Find the middle ground. 💡 Pro Tips: Keep it under one page (3–4 short paragraphs max). Often the tone of the announcement will give you clues as to how to match the tone with your cover letter. Use plain language. If I need a dictionary, you’ve already lost me. (This includes acronyms, never assume the person reading a cover letter knows anything about your previous world of work, if you make me have to think about what something means, I am moving on). Always write to the reader . What problem do they need solved? (It is always in the announcement) How are you the solution? (Come right out with it: I am level III certified in______: Current security clearance of_______: Decade of specific experience with_____ at the $_____ level). You will see from the announcement what they are looking for. ✍️ If you see something repeated in the job announcement a few times, ( even if re-worded a few different ways ) you know that skill is a key one, and important to highlight. 🎯 The Bottom Line A cover letter won’t get you hired. But it can get you noticed. And that’s the whole point — to move you from paper to interview. Don’t write a snooze note. Write something that makes the hiring manager think, ✍️ “This one’s worth a closer look.” If you found value in this, please hit follow, sign up so you get notified when new posts come out. Consider buying a coffee to help support the site. Definitely reach out if you want resume, research, or interview skills support. Thank you.