
“Bill of Health” Issue No 2 - Losing 50 Pounds: How I Did It
- Bill Sindewald
- Jun 25
- 7 min read
Just like it took me a while to figure out a sustainable way to manage my mental fitness, it took a lot of trial and error to figure out the physical side too. First it was getting under 200, then 180, then 170. I ended up losing 50 pounds over the years doing this stuff. There was even a stretch where it got so dialed in that I was dropping weight without even thinking about it.
But I'm going to be real with you. During that dialed-in stretch, I was running nearly five days a week. Six years later, I'm about 190, working my way back to 170–175. Honestly? I think I look pretty good. But I know my own body, and to get that flatter belly I'm after, I've got to lock back in. That's exactly why I'm writing it all down — these are the tips that got me here, and the ones I'm tightening back up right now.
Losing weight is easy, just like running a marathon is easy — burn more calories than you eat, and run from the start line until you've covered 26.2 miles. See? Easy.
If I could go back in time and talk to my 22-year-old self, here are the tips I'd give him — and the ones I need to lock back in on myself.
Tip 1 — Watch Your Portions
"Look at how much food that actually is!"
That's what a friend said to me one night, staring at my plate. And he was right — I'd used every inch of it, piled high, kind of taking advantage of the "it's only one serving" rule. One serving… that was probably three. To say I had an appetite is an understatement. That was the moment I started actually paying attention to how much I was putting away.
Plate one serving and put the rest in the fridge before you sit down. Big appetite? Eat a piece of fruit, drink a big glass of water, wait 10 minutes before going back. Build dinners around protein, veggies, and hearty grains — and track your intake for a week. Using Lose It! was a real awakening for me. For the first time I actually saw how much I was eating and what each thing was costing me in calories — some of my "normal" portions were brutal once the numbers were staring back at me. For context, in a big Kaiser Permanente study, people who kept a daily food diary lost about double the weight of those who didn't. The act of tracking itself moves the needle.
Tip 2 — Go Plant-Based
I changed how I ate so I wouldn't go out the way my dad did.
Before I truly went plant-based, I focused on getting fruits and veggies into every meal — especially fiber, as much as I could get. It keeps you full longer, though hitting the recommended ~30 grams a day is harder than it sounds — about 95% of Americans don't manage it. That's almost everybody coming up short. I hit my stride once I started having a smoothie every day. I'd hide spinach or kale in there with frozen fruit and chocolate protein powder, using carrot juice as a binder, plus flax, hemp seeds, and oatmeal. Such a great way to get a tasty, nutritional meal into your day.
Then in 2021 — a couple years after I hit my weight goal in 2019 — I challenged myself with Whole30, which is extremely difficult, then tried Meatless May. Honestly? Meatless was WAY easier. After a month of breaking my grocery and cooking habits, I had a whole new perspective. Plus, I always say veggies can f*ck — meaning people assume you can't get a good, tasty vegan meal, and they're dead wrong. The creativity that comes out of building a meal without meat is unlimited, and it can taste really good. Get an air fryer and tofu becomes a tasty sidekick.
The more I read, the more it just made sense: going plant-based lowers your risk of heart disease and cancer, and heart disease is the whole reason I started any of this. I wasn't eating much dairy at home anyway, so it wasn't a huge leap. Plus, we're the only species that drinks another species' milk — and there's a reason women only produce milk when they have a kid. Most people are lactose intolerant anyway; the NIH estimates about 68% of the world's population has trouble digesting it. And vegan cheeses have come a long way — they actually taste good now.
And don't buy the myth that you can't get strong without meat. Patrik Baboumian won Germany's Strongest Man and set multiple Guinness World Records on a fully plant-based diet — including carrying over 1,200 pounds. Some of the most powerful animals on the planet — gorillas, elephants, rhinos, oxen — are pure plant-eaters too. You're not going to wither away on beans and tofu.
You don't have to go all-in overnight. Try one meatless month and see how it feels.
Tip 3 — Cut the Bad Habits: Alcohol and Late-Night Snacking
Two habits that quietly undo all the others.
These two go hand in hand, so I'm lumping them together. Start with alcohol — there's a reason it comes with a warning label. It's the human tax: you pay more and get no real benefit. Think about what you're actually doing — you're drinking bread. For most people, cutting carbs is one of the fastest ways to lose weight, and alcohol is just carbs you drink. But it's worse than that. One night out can wipe away a whole week of progress, and it kills your willpower too. Most times I drank, the night ended with a late-night fast food run.
And that's the other half of it. If you're eating a full meal right before bed — drunk or sober — there's about a 90% chance that scale is up the next morning. Try your best not to feed the late-night craving; every night you skip it, the next one gets a little easier.
Here's what made it click for me, long before I quit for good: every six months or a year I'd do a reset and take a full month off. Every single time, the weight came off way easier. Then one night — hugging the toilet — I asked myself, why am I doing this to myself? That one stuck, and eventually I just stopped for good.
Try a sober month and see how you feel. You might end up asking yourself the same question.
Tip 4 — Cardio
Find your thing, and perhaps a headband to go with it.
Find an activity you actually enjoy — one where you don't even think about it being a workout. For me it was basketball. I got a YMCA membership and went nearly every day, playing for hours — and that's where the genesis of Headband Bill really began. I was playing point guard, waiting for my team to set up, and I needed a second to wipe the sweat out of my eyes. While I was doing that, my opponent tried to steal the ball! I was like, hey man, I'm trying to get situated over here. He didn't care — nor should he. First I tried cutting the sleeves off my shirts to use as sweatbands, then bandanas, but nothing did the trick. Then I discovered the headband. The rest is history.
Pick something you actually look forward to — if it feels like fun, you'll keep coming back.
Tip 5 — Intermittent Fasting
You don't need a strict plan. You need a window — the 8 hours you're going to eat.
Honestly, this one came out of working second shift and being locked in on work. I'd drink my coffee and not think about food at all. I'd find myself not even eating the breakfast I'd packed until lunch.
The key is picking an eating window that fits your day, and prepping your first meal ahead so it's ready when you're actually hungry.
Tip 6 — Train Your Muscles
Strong body, stronger head.
Early in my journey I made a commitment: work out on my lunch break, lift at least four days a week. Shoulders and tris, legs, chest and bis, back — abs every other day. I've gotten off that routine, but I'm getting back into it — these days I'm aiming for at least two whole-body workouts a week. And it doesn't have to be weights — bodyweight workouts do the job too. A good lift keeps your body burning calories for hours after you're done, and the guidelines say to hit all your major muscle groups at least twice a week. But honestly the bigger thing for me was how it felt. I felt stronger, and I felt better about myself.
Don't overthink the split. Getting each muscle group in once a week is a great start — build from there. Protect the time like a meeting.
Tip 7 — Mobility & Stretching
You don't need the splits. You need to get your body prepared.
I'm still refining this one, but here's what I'd tell my younger self, and what I'm telling myself now: you don't need a 45-minute routine or to touch your toes on day one. Just move through your full range of motion a little every day — neck, shoulders, hips, spine, ankles. The goal isn't doing the splits. The goal is getting your body a little more limber before you challenge it. Right now I'm building my own routine around that viral Qigong-inspired warm-up — the jumping, body waves, golf swings, and some other stretching mixed in. I also just found out Garmin has a built-in mobility routine on the watch that's been really helpful, and I've started doing that too.
Start with five minutes a day.
Tip 8 — Accept the Process, Don't Fixate on the Numbers
Don't let one number run your whole day.
It can be demoralizing when you're trying to lose weight and you hit a wall. But know that if you're committing to a healthier lifestyle, the results are coming whether the scale shows it that week or not.
Commit to the lifestyle and let the results catch up.
Here's the honest truth: managing your health is always going to be a challenge. Things change, you change, and you have to find a system that works for you. These eight are the main things I've leaned on — the fundamentals, based on evidence, not hype. But how I do it will keep evolving, and yours should too.
If you're looking to make some progress, don't try to overhaul everything at once. Pick one of these, see how it works, then add another. I spent years avoiding the start line — take it from me, start with small steps and the rest gets easier. Every second you invest in improving yourself has an incredible ROI.
Like I said: losing weight is easy. Executing it is another thing entirely. So let's do this together.
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