9 Pieces of “Good” Advice That Cost Me Years (Even the Ones From People Who Love Me)

Most of the advice that hurts you sounds smart. The damage comes from following it past the point where it stops working. Here’s where each one breaks, and what I do instead.

I went to rehab and jail twice before I turned 17.

People gave me advice my whole life. Almost all of it came from a good place, and a lot of it would have kept me exactly where I was.

Since then I’ve built several multimillion-dollar companies, a beautiful family, and a life I didn’t think was possible. Some of the biggest turns came from questioning advice I’d been told to follow. Here’s the advice I’d push back on if I were 20 again.

1. Follow your passion

My first two businesses, a vacation rental site and a hosting company, both failed.

I was passionate about the wrong thing. My brother and I borrowed $10,000 from the bank so I could sit in a server room nerding out on hardware. I loved it. Nobody was paying me for it.

Passion without market demand is a hobby. The guy with the model train set in his basement isn’t making money off those trains. The person who sold him the trains is.

When a young person asks me what to do with their life, I give them four questions:

1. What are you naturally good at, that other people struggle with?
2. What do you love doing?
3. What does the world need? Go on YouTube or social. People are very vocal about what they’re pissed off about.
4. What do people already pay for?

Most people answer the second one and skip the rest. You don’t have to give up what you love. You just need enough people willing to pay for it.

2. Never give up

I once watched a guy pitch a board game on American Inventor. He’d spent 27 years and his entire life savings on it. Every judge said no, and he still swore it would be a hit.

Bro. Nobody’s bought it.

“Never give up” keeps you in an approach long after it’s dead. Add sunk cost, the feeling that you’re $50,000 in so you have to see it through, and you’ll stay with something that’s hurting you just to say you didn’t quit.

If your main reason for continuing is how much you’ve already spent, or proving people wrong matters more than the goal, run this check. Write the goal down. Then ask: knowing what I know now, if I started from scratch, would I do this again? Compare the current approach to the alternative and pick the one with the best shot.

You’re allowed to give something a real shot and still decide to stop. The goal stays. The path changes.

3. When you’re stuck, go harder

When my brother Pierre started his construction company, his plan was land development, new homes, leases, renovations, and multi-unit projects. To him it was all construction.

I told him, “You’ve got four or five businesses and you’re pretending they’re one. Any one of them could do $10 million a year if you focused. Run all of them and you won’t do any of them great.”

He picked one and went all in. Today he’s the largest home builder in Eastern Canada, a nine-figure entrepreneur. Zero chance he gets there trying to do everything out of the gate.

I see the opposite in founders who start missing numbers. They add meetings, add projects, add more, and their attention splits. A garden hose sprays water everywhere. Push that same water through a pinhole and it cuts steel.

The fix is something I call the commitment cut:

1. List every commitment you have for the next 90 days.
2. Circle the three with the biggest impact on what you’re trying to achieve.
3. Circle the one with the least impact, and stop doing it.
4. Give the time you freed up to your top three.

When you’re stuck, go harder on less.

4. Listen to your loved ones

This one breaks my heart, because I’ve done it to my own kids.

One of my sons came to my wife and me with a business plan. Not his first. We’d watched a few others fizzle, so we got hypercritical. The idea wasn’t bad. We just didn’t trust him to finish.

Afterward I asked my wife, “Are we doing that thing parents do, where we don’t want to see them fail?” It’s teaching a kid to ride a bike. You know they’re going to fall, so you never want to let go.

So I went back to him. I explained where my concerns came from and told him that if he went in eyes wide open on the money, the marketing, and the effort, I was there to support him. The next morning he came back. He’d done more research and decided not to do it. I never told him no.

Here’s the hard part. Take advice only from people who love you and you’ll get the life they had. Even I’m a flawed advisor for my own kids. I care too much to give them the YOLO advice I’d give a stranger.

So build your Mount Rushmore of advisors. Pick five people whose lives you admire for different reasons (business, family, risk-taking, problem-solving) who have the receipts for the thing you want. Some of mine I know personally. Some I don’t yet. When I’m stuck, I ask what Warren would do.

When your family pushes back, listen with affection. They don’t want to watch you skin your knee. Then go get advice from someone who’s done it.

5. Always have a plan

At 23, on my third company, I sat in a basement apartment with software called Business Plan Pro and spent 25 hours on the perfect plan. Perfect pro forma. Perfect marketing strategy. Perfect recruiting plan. Perfect offer.

None of it came true. I call it a guess plan now. Those 25 hours could have landed my first customer.

Mike Tyson said everyone has a plan until they get punched in the face. If your launch date keeps sliding, or everyone you know has heard your idea and nobody has used it, you’re planning instead of learning. I’ve followed founders who’ve been “launching” for nine months. Still haven’t seen the product.

I start every business assuming I don’t know what will work. Make the decision, then make it right:

1. Make doing non-negotiable. Sell, build, or create. Thinking doesn’t count.
2. Set a deadline. Goals are dreams without one.
3. Add a reward and real stakes. You’ll do ten times more to avoid pain than to gain pleasure. Skipping a Bali trip you weren’t taking anyway doesn’t count. Having to find another job does. Ask Jen.
4. Make it public. Post the goal, the date, and what happens if you miss.

Then take one default action, right now. Those two words are written above my office door.

6. If you want it done right, do it yourself

Founders who do everything themselves end up burned out, and the whole team waits on them. That’s why it’s called a bottleneck.

People don’t buy your presence. They buy your standards. Even if you’re a coach and you think they bought you, they bought your method and the way you do it. Your job is to set the standard, build the system, and train people against it.

Break down a workflow like sales call, onboarding, delivery, follow-up, billing. Maybe only the delivery truly needs you. Everything else gets a checklist and training so nobody can do it wrong.

If your team needs your approval for every small decision, or you keep fixing work for people who fall short, you’re teaching them that you’ll always jump in. The fastest way out is the camcorder method:

1. Pick one task you do over and over. Email replies, support tickets, financials, social posts.
2. Record yourself doing it on Zoom with screen share. Talk out loud through every step, including why you make each choice.
3. Hand the recording to someone on your team, or an AI agent, and have them turn it into a step-by-step playbook and fill in anything you missed.

Explain the principles and they learn how you think. Your team isn’t the problem. They just haven’t been given the tools.

7. Hustle harder

When I built my first real company, I was coming off two failures and terrified of a third. Customer calls on Sundays. Interview prep at 6 a.m. For three years I was on site deploying software for clients eight hours a day, then running the company on top of it. I napped between meetings.

I couldn’t keep relationships. I put on weight. Eventually I got shingles. My body basically said, “You think I don’t notice? I notice.”

There are seasons where you push. But after my full-distance Ironman it took me six or seven weeks to recover, and work is no different. If you check messages every time you’re supposed to be off, keep postponing sleep and the people you love, and snap at everyone, you’re past the season.

Put recovery on the calendar first. I run a yearly rhythm of trips I never skip, built around the three Fs: fun, frequent, and with friends. People see my snow bike and wake surf trips and ask to come. I tell them to grab two people and start their own ritual.

I’m happier when I take time for myself, which makes me better for my team. I still work hard. I just stop burning energy fixing things that slid and cracked.

8. Be yourself

If I’d kept being myself at 19, I know exactly where I’d be. Still drinking, still smoking, still hanging out with people I shouldn’t, still obnoxious.

Keep the best parts of you. The part that screams at people and makes bad decisions has to die.

Change is hard because we label ourselves. “I’m a night owl.” “I’m an introvert.” Once you say it, you feel pressure to stay consistent with it. And “that’s just me” ends every conversation right when it’s time to step up.

Confidence comes from keeping the commitments you make to yourself in private. Break those and you break your belief in what’s possible. So use friction: make the hard thing easy and the easy thing hard.

Want to go to the gym? I lay my clothes out the night before, commit to a friend who’ll call me out if I don’t show, pay real money for a trainer, and post a picture after. Want to stop gaming? Sell the console and only play at a friend’s house.

Know your weak spots and plan for them before they take you out.

9. Never show weakness

This is the one I struggled with most.

For 15 years after rehab I told no one. Not my friends. Not the girlfriend who later became my wife.

Then I was asked to give a talk where the best speaker would win $25,000 for their charity. I picked Portage, the rehab center that saved my life as a teenager. A talk about growth hacking wasn’t going to win, and I knew it.

An hour before I went on, I asked my wife to stick around afterward, because I was going to share something I’d never told her. She mentioned her parents were coming to watch. I asked her to make sure they stuck around too.

I broke down for 15 minutes on that stage. Afterward my mother-in-law, who I’d always butted heads with, gave me the biggest hug and said, “I understand you now.” Tim Ferriss walked up and said he’d had no idea.

The best-selling book, the 16 million followers, the six-figure keynotes all came after I got honest about my story. The more personal the story, the more universal the message. When you only share wins, nobody can relate.

Start with one person. “Can I share something with you? A couple of weeks ago I really struggled with this. Here’s what happened, here’s what I learned, and here’s where I’m at now.” Then watch how they respond.

When you go first, people tell you things they’ve never told anyone. It happens to me dozens of times a day. The people who matter won’t judge you, and the ones who judge don’t matter.

Most people who give you advice mean well. They just don’t have the full context, and neither do you. Say thank you. Then question it before you follow it.

-DM