Winning in this season means earning people's trust and you only do that if you let them get a glimpse of how your mind works before you ever even try to sell them anything. One of the weird successes I had wasn't exactly what I expected at first, by posting about the honest mistakes I've made along the way, it felt a bit scary but it ended up leading to way more real conversations with potential partners and not just a bunch of form letters. I broke with the rule of only ever sharing the successes and started actually explaining the thought process behind what I do. That shift ended up attracting people who are actually thinking about their business decisions and not just looking for a quick fix. Now people are reaching out to me because they already kind of get me, and that's saved me months of going back and forth with people who wouldn't have been a good fit anyway. For me, winning looks a whole lot like building trust and long term relationships rather than just churning out quick wins.
The rule I broke was the idea that all client relationships should run through a single leader. I invited potential customers to connect directly with the team member whose expertise best fit their needs, and led with a collaborative approach. It changed everything by making our experts visible, showcasing the strength of our women-led business, and helping us break barriers in a male-dominated industry.
Winning for me now is about resilience and using my story to help others move through hard seasons. A win that didn’t look like success at first was defying a personal diagnosis and turning that struggle into a way to model how to face tough obstacles with determination. I broke the unspoken rule that leaders should keep challenges private by sharing the journey openly, and that choice changed the impact of my work.
**Winning** right now means converting a virtual office inquiry into a five-year tenant relationship--not just closing a quick sale. At ViewPointe, I stopped measuring success by how fast I could get signatures and started tracking something different: how many clients renew after their first year. When our attorney clients stay for 3+ years (currently 68% do), it tells me I matched them correctly from day one, not oversold them on square footage they'd never use. My biggest "loss" was turning away a lead who wanted our premium corner suite but clearly only needed mail service and occasional conference room access. I walked them down to a virtual office package at one-fifth the price. They've been with us for four years now, upgraded once organically, and referred six other attorneys who actually did need full suites--that's $47,000+ in revenue from a sale I "killed." The win that didn't look like one. The rule I broke: I stopped using our CRM (Follow Up Boss) the way it was designed--as a push system to move leads through a pipeline fast. Instead, I built what I call a "fit filter" where I actively talk people *out* of services during findy calls if their business stage doesn't match. Most coworking spaces want every butt in every seat. I've had 90-minute calls that ended with me recommending they stay home another year. Conversion rates dropped 11%, but retention shot up 34%, and our Yelp reviews specifically mention "honest advice" more than amenities. Turns out people remember when you cost yourself money to help them.
Winning for me right now looks like the crew truck pulling away at 4 PM instead of 7 PM because we finally nailed our scheduling system. We're a landscaping company in Roslindale serving Greater Boston, and for years I wore "working until dark" like a badge of honor. Then I realized our best installers were burning out and our mistake rate on hardscape projects was climbing every summer. My unexpected win was a commercial snow management contract we almost lost in 2019. The property manager wanted us to pre-stage equipment at their site, which meant buying a second plow truck we couldn't really afford and parking it essentially unused for 10 months a year. We did it anyway, and that client referred us to four other commercial properties because nobody else would commit equipment that way. Those referrals now make up 40% of our annual revenue--all because we said yes to something that looked financially stupid on a spreadsheet. The rule I broke was "never turn down work during peak season." Every landscaping company I knew operated on "say yes now, figure it out later" during spring and fall. Three years ago I started capping our seasonal cleanup bookings at 15 per week instead of taking every call. We lost some revenue that first year, but our Yelp rating jumped from 3.8 to 4.7 because we actually showed up on time and did thorough work. Now those same customers call us first for $30K patio installations instead of shopping around.
I'm a family law attorney in North Carolina, and "winning" used to mean the biggest settlement or custody victory. Now it's when I get a quiet email months after a divorce telling me both parents showed up to their kid's birthday party without drama, or when a client texts that they closed on their first solo home purchase. My biggest win that looked like failure happened in 2010 when my solo practice merged with another firm. I thought I'd failed at independence. That merger taught me systems I never had alone, and when I later reopened as Greensboro Family Law, I knew exactly how to build infrastructure that could handle complex surrogacy cases and LGBTQ+ family formations--work that requires serious operational backbone, not just legal skill. The rule I broke: I stopped pretending every divorce needs a warrior. The industry sells combat, but I walked away from litigation-first billing models. My MBA background showed me the math--trials cost clients $40K+ and deliver outcomes they hate. I got certified in collaborative law and mediation instead, which was professionally weird in 2008 when everyone wanted a "bulldog." Now 90% of my cases settle outside court, my clients keep their money and sanity, and I don't spend my life in a courthouse watching families implode for procedural points. I also put estate planning conversations in the divorce process upfront, not after. Most attorneys hand you papers and say "update your will later." I make clients address power of attorney, guardianship, and trust structures during separation because I've seen too many people die with their ex still controlling their medical decisions or inheriting their retirement accounts. It's uncomfortable but it's honest, and clients refer their friends because we handled the stuff other lawyers avoid until it's a crisis.
**Winning** right now means watching a technician I trained explain water filtration to a homeowner with the same precision I used to teach ITIL frameworks to government employees. When our team can break down why Arlington's municipal water contains more chlorine than a swimming pool--and offer solutions without pressure--that's success. We measure it by callback requests: when customers specifically ask for a tech by name, we know the mentorship is working. My biggest "failure" was walking away from DOJ contracts and security clearances to join my husband in residential plumbing during COVID. Friends thought I was crazy leaving that stability. But that decision let me build something I couldn't in government work: a company where every technician gets vetted with background checks, where we create actual job growth in Northern Virginia, and where blind and sighted customers get the same stress-free service. That "step backward" now supports multiple families with $70K-90K average earnings and zero weekend shifts. The rule I broke: applying IT service management methodology to trades work. Plumbing companies don't typically run on ITIL frameworks--that's for tech infrastructure. But when I mapped our scheduling, service delivery, and customer communication using those same process-driven systems, our efficiency jumped enough to offer 9-to-5 schedules with no on-call rotation. Technicians stopped burning out, and our small service area (just Arlington/Falls Church) became an advantage instead of a limitation because we eliminated Beltway commute waste. We also stopped hiding our licensing levels and vetting standards. Most plumbing companies don't advertise their background check policies or explain what Master Plumber certification actually means. We put it on our careers page and website because families with kids--especially those with accessibility needs--deserve to know exactly who's entering their home. Transparency costs us nothing but builds the kind of trust that turns one-time customers into PTA parents who refer us to their whole school network.
Winning now means watching someone recognize their own pattern before it destroys another relationship. I've worked in addiction and trauma treatment for 14 years, and early on I measured success by completed treatment programs and sobriety milestones. Now it's when a former client texts me that they caught themselves repeating a codependent behavior with their new partner and actually stopped mid-sentence to set a boundary instead. My biggest win that looked like total failure was a client who relapsed three times during our work together. She kept apologizing, I kept adjusting our approach--switched from traditional CBT to Narrative Therapy because her brain didn't respond to cognitive restructuring the way textbooks promised. Two years later she's running peer support groups and tells people that learning there wasn't one "right" way to heal gave her permission to figure out what actually worked for her nervous system. That's 40+ people she's now helping because we didn't give up when the standard protocol failed. The rule I broke was the 50-minute session. I had a 16-year-old client with ADHD and TBI who'd shut down right at the point where real processing could happen. Insurance and training say you stick to the hour, bill accordingly, wrap it up. I started watching her body language instead of the clock and would end sessions at 35 or 47 minutes when her system hit capacity. She kept coming back, started trusting the process, and her mother said it was the first time someone didn't try to force her daughter into a therapeutic box that didn't fit her brain.
Winning for me right now is watching a client's conversion rate climb from 1.8% to 4.3% after we stripped their homepage down to six lines of copy. They had invested $40K in custom animations and a 2,000-word manifesto above the fold. We deleted most of it, clarified their one core promise, and their revenue jumped 140% in eight weeks without spending another dollar on ads. My unexpected win was losing a $180K retainer because I told the founder their offer was the problem, not their marketing. They wanted us to fix their funnel, but their pricing model made no sense and their messaging tried to serve three different audiences at once. Six months later they came back after restructuring everything--we've now been working together for three years and they've scaled past $12M annually. The rule I broke was the agency model of locking clients into long contracts with vague deliverables. I started showing clients exactly where their bottleneck was in the first call--for free--even if it meant they could fix it themselves. About 30% do go fix it on their own, but the other 70% come back because they trust we're not just selling them services they don't need. Our client lifetime value is 3.2x higher than when we used traditional sales tactics.
"Winning" now means watching a nurse walk out of our Lincoln store actually excited about going to work because her scrubs finally fit right. For 27 years I've run Uniform Connection, and I stopped chasing revenue targets when I realized our real metric is whether healthcare workers feel confident enough in their uniforms to focus on saving lives instead of adjusting their waistbands. My biggest disguised win was our VIP Scrub Party concept that seemed ridiculous at first--who throws private shopping parties for medical staff? We require a 20-person minimum, offer 15% off, and I personally wondered if anyone would bite. Now hospitals book us when they're changing uniform colors, and those parties generate more word-of-mouth than any ad I've ever bought. Turns out caregivers rarely get treated like VIPs, so when we close the store just for them with refreshments, they remember it. The rule I broke: I rejected the retail playbook that says "stack inventory deep and rotate fast." We carry sizes from XS-Petite through 3XL-Tall in multiple inseam lengths because I got tired of telling a 5'2" ICU nurse or a 6'1" surgical tech that their size was "available online." It kills our inventory efficiency and my accountant hates it, but 80% of our business is repeat customers who know we'll have their size in-store, today, when their scrubs rip during a 12-hour shift. We also donate rejected returns to People's City Mission instead of processing them as waste. Can't resell embroidered or altered scrubs anyway, and it costs us nothing to redirect them where they help someone re-entering the workforce. Healthcare workers notice we're not just talking about community--they see the donation bins.
I run operations for a sewer and drain company in North Carolina, and winning right now means solving a problem in one day instead of one week. Last month we coordinated 14 trenchless repairs during peak season without missing a single callback or leaving a customer wondering when we'd show up. That's the win--nobody's yard looks like a war zone, and families can flush their toilets by dinner. My unexpected win was a job in the Ardmore neighborhood where we lined 100 feet of failing sewer pipe under a concrete slab and through the yard. After we finished, the homeowner called because their kitchen was backing up--turns out their drain connected to an old floor drain we'd sealed during the repair. My crew thought I was crazy for eating the cost to fix our oversight, but that customer left a detailed review that's brought us six jobs since. Doing right when you screw up converts better than any ad spend. The rule I broke was "always give three options." Standard sales wisdom says offer good/better/best so customers pick the middle. I started telling people when hydro jetting would fix their problem for $600 instead of pushing our $8,000 pipe lining service. Our average ticket dropped 15% that quarter, but our callbacks for bigger work doubled because customers trusted we weren't just upselling. Now half our lining projects come from people we cleared a drain for six months earlier--they call us first when the real problem shows up.
I've been in the carpet cleaning industry for years, working with franchise owners and service businesses from the ground up. "Winning" now means watching a business owner actually leave for vacation without their phone glued to their hand, or when a technician I coached gets promoted to manager because they finally understood that customer retention beats one-time sales every single time. Our biggest "loss" that turned into a win: I pushed one franchise owner to raise their prices by 40% when every competitor was racing to the bottom. He lost three price-shopping customers immediately and thought I'd destroyed his business. Six months later, his schedule filled with higher-quality clients who actually valued the work, his techs stayed longer because they weren't burning out on cheap jobs, and his profit margin jumped enough to buy a second truck. Those three customers he lost? They came back a year later after trying the cheap guys and dealing with recurring stains. The rule I broke: I stopped letting cleaning companies hide their prices online. Everyone in the industry said "every job is different, we need to quote on-site"--which really meant they were scared of competition. I had our team put clear pricing ranges on the website with explanations of what affects cost. Our phone calls dropped by 30% but our booking rate jumped to 67% because people who called were already pre-qualified and ready to schedule. Transparency scared off tire-kickers and attracted customers who understood value. I also made our operations team track "referrals from real estate agents" as a primary KPI, not just total revenue. Most cleaning companies chase residential customers randomly, but agents send multiple clients per year if you prove reliable. We started measuring agent relationships like gold, and that single metric shift grew one location's business by 40% in eight months because we were finally tracking what actually multiplied revenue.
Winning right now means watching a customer's face when they open their front door after installation and actually tear up because the floor transformed their space more than they imagined. I've been sourcing flooring factory-direct by the container since 2010, and that moment when someone realizes they made the right choice--that's what keeps me doing this. My unexpected win was a rental property owner who bought our cheapest vinyl because "tenants destroy everything anyway." Six months later, she came back furious--not because the floor failed, but because it looked so good she realized she'd been undervaluing all her properties. She spent $47,000 upgrading four more rentals with mid-range options and increased her rents enough to cover the cost in eight months. Now I actively talk landlords *up* from bottom-tier products because I've seen the ROI. The rule I broke was our industry's "measure twice, order once" gospel. I pushed our family business to implement a 90-day return policy on unopened boxes with no restocking fee when everyone said we'd get slammed with returns. We've had it for years now and returns are under 3%. Turns out when customers aren't terrified of ordering wrong, they buy more boxes upfront instead of under-ordering and facing delays. Our average order size jumped 18% and installation complaints dropped because installers aren't piecing together shortage fixes.
I'm a 25-year-old running LGM Roofing in New Jersey--took over from my dad six months ago after he ran it solo for nearly two decades. I also own a dumpster rental company and a LED sign business, so I've learned what "winning" actually means when you're building multiple things at once. Right now, winning looks like my father not being the only person carrying the weight anymore. For 18 years he did everything himself--sales, installs, paperwork, scheduling. The win isn't our GAF Master Elite status or the revenue growth. It's him finally being able to step back because we built systems that work without him being in three places at once. My unexpected win was the dumpster company I started right after high school. Everyone saw it as a side hustle that distracted from "real" opportunities. It looked messy and unglamorous compared to what my peers were doing. But that business taught me operations, customer service, and scaling in ways no classroom could--and those exact lessons are why I could step into a 25-year-old roofing company and actually grow it instead of just maintaining it. The rule I broke was waiting until I was "experienced enough" to lead. At 24, I walked into my dad's established business and started changing things--scheduling systems, customer communication, operational structure. The roofing industry expects you to pay dues for years before you get a voice. I brought fresh systems thinking from running other businesses and applied it immediately. That impatience to improve things rather than learn the "right way" first is exactly why we've grown faster in six months than we did in the previous three years.
I've been the Fitness Director at Results Fitness in Alexandria for years now, and I can tell you "winning" used to mean packed classes and full training schedules. These days? It's watching a 62-year-old woman who couldn't do a single bodyweight squat six months ago deadlift 135 pounds with perfect form. That's the metric I actually care about. My unexpected win was when I stopped letting people skip the boring stuff. Early in my coaching career, I'd let clients bypass mobility work and warm-ups because they wanted to "get to the real workout." One woman kept complaining about shoulder pain during BodyPump, so I finally made her spend three weeks doing nothing but corrective exercises and CX WORX core work--no heavy lifting allowed. She was furious at first. Two months later, she hit a PR on her overhead press and told me those "boring" weeks changed how her whole body moved. Now I refuse to let anyone skip foundations, and our injury rate dropped while strength gains went up. The rule I broke was the fitness industry's obsession with constantly switching up programming to keep things "exciting." Every gym around us was doing themed workout weeks and trendy challenges to retain members. I went the opposite direction--we built progressive overload programs that looked almost identical week to week, just with slightly heavier weights or one more rep. People thought it was too repetitive. Turns out, when you actually track someone's progress from 15-pound dumbbells to 35-pound dumbbells over four months using the same movement pattern, they get addicted to that tangible growth. Our retention is stronger than it's ever been because people can see exactly how far they've come, not just how entertained they felt.
What does winning look like now? Watching 2,500 event planners from Google, JP Morgan, and Blackrock walk out of our Event Planner Expo energized instead of overwhelmed. Early in my career at Estee Lauder, I thought winning meant hitting quarterly sales targets. After 20 years in this industry, I've learned it's about the planner who texts me six months later saying their career changed because of a connection they made at our conference. My unexpected win was the year our keynote speaker canceled 48 hours before showtime. I scrambled, completely panicked, and ended up restructuring the entire day around interactive workshops instead of one big presentation. Attendee satisfaction scores jumped 31% that year. Turns out people were tired of being talked at--they wanted to actually do something. That "disaster" became our new format, and we've built the leading events conference in the US around peer-to-peer learning ever since. The rule I broke was the event industry's obsession with flawless execution over genuine experience. Everyone said attendees expected perfection--any visible mistake would tank your reputation. I started being honest when things went sideways. When our AV failed during a product launch for a major cosmetics client, instead of pretending everything was fine, we acknowledged it immediately and turned it into an impromptu networking break. The client's team generated three times more qualified leads during those unplanned conversations than they did during the scripted presentation. Now we intentionally build "white space" into our run-of-show documents specifically for these unscripted moments.
**What does "winning" look like in this season of your life?** Winning right now means watching a contractor go from skeptical about AI to closing 30% more jobs because their website answers customer questions before the phone even rings. When we launched our AI-enabled platform at CI Web Group, I measured success by how fast we could build--600 pages in 90 days versus competitors taking six months for 50. But the real win is seeing a plumbing company owner finally take a weekend off because their lead qualification runs itself. **Share a win that didn't look like success at first.** Blowing up our entire business model last year felt like chaos. We gutted our systems, rebuilt our tech stack, and launched JustStartAI while simultaneously overhauling how we served clients. Revenue dipped, the team was stretched thin, and I questioned everything. Twelve months later, we're closing deals 40% faster, our client churn dropped to 1%, and contractors who were drowning in manual work are now scaling without adding headcount. What looked like reckless risk was actually the only path forward. **What's one rule you broke that changed everything?** I stopped selling marketing. Every agency in our space pitches SEO packages and ad campaigns like they're magic pills. I started telling prospects the truth: if your operations, sales process, and customer service are broken, no amount of traffic will fix it. We lost some deals to competitors who promised easier answers. But the clients who stayed grew 34% year-over-year because we aligned their entire business system--not just ran ads. Turns out honesty about what actually drives results builds better businesses than overpromising on marketing alone.
I run operations for one of Australia's top cladding suppliers, and winning right now means my team can answer customer questions without me in the room. After 20+ years in business management, I've learned the real win isn't being the smartest person on the floor--it's building a team that doesn't need you for every decision. My unexpected win was our return policy becoming our best sales tool. We implemented a strict 14-day return window with detailed damage documentation requirements--most suppliers told me I was making it too complicated. But that "complicated" process dropped our illegitimate claims by 60% while our repeat customer rate jumped. Customers trusted us more because we were thorough, not less. The rule I broke was assuming B2B suppliers can't be DIY-friendly. Everyone in commercial cladding focuses on contractors and builders--we decided to make our WPC cladding accessible to homeowners doing their own installs. My sales team thought I was crazy splitting our focus. Now those DIY customers are our fastest-growing segment, and they refer more contractors to us than our own outreach ever did.
**Winning** right now means watching our clients publish content confidently without needing my approval on every post. When I started RMS in 2015, success was landing big contracts and staying billable. Now it's hearing a government agency tell me their team finally understands SEO strategy, or a mortgage broker running their own campaign without us. My unexpected win was losing a corporate client who demanded we copy their competitor's exact playbook. I said no and they walked--terrifying when you're building an agency. Six months later, three referrals came from *that same client's team members* who'd moved to other companies and specifically wanted an agency that "actually pushes back when something's wrong for our brand." Turns out integrity scales better than compliance. The rule I broke was the agency model of specializing narrow and niching down hard. Everyone said pick one service, one industry, one client type. Instead, we built deep expertise across SEO, video production, content strategy, paid media--the whole stack--specifically for regulated industries that get ignored by trendy agencies. Our mortgage and finance clients don't need another social media guru; they need someone who understands compliance *and* can make their content actually perform. That combo is rare, and it's why we retain clients for years instead of months.
"Winning" for me right now looks like empty maintenance request queues and residents who renew their leases without us even asking. When you're managing marketing for 3,500+ units across multiple cities, success isn't flashy campaigns--it's people choosing to stay because their oven works and someone actually listened when they had a problem. My unglamorous win was spending hours watching Livly feedback data and realizing residents kept complaining about the same stupid thing: they couldn't figure out how to turn on their ovens after moving in. We made simple FAQ videos for maintenance staff to share during move-ins. Move-in dissatisfaction dropped 30% and positive reviews went up. Nobody writes case studies about oven tutorials, but that boring fix improved occupancy rates more than any paid search campaign that quarter. The rule I broke was the property management obsession with broker fees and traditional ILS spend. Everyone said you need brokers to fill units and max out your ILS budgets. I cut broker fees almost entirely and reallocated that money into creating in-house video tours and better digital targeting through platforms like Digible. We leased up 25% faster, cut unit exposure in half, and saved 4% of our $2.9M budget while hitting occupancy targets. Turns out showing people actual units on video works better than paying someone else to do it.