You'll Never Meet Your Deadline (Unless You Fix This)

You know that one thing you’ve been telling yourself you’ll start?

Writing the book.

Quitting the job.

Having that conversation.

Yeah, me too.

Back in 2021, I told myself I’d launch this newsletter in three months. And then spent nine months doing... absolutely nothing about it.

I had the deadline. I had the dream. But instead of taking action, I treated the deadline like a suggestion. Something I’d “get to eventually.”

Eventually turned into a year.

Why? Because self-imposed deadlines are a completely different beast. There’s no boss breathing down your neck. No teacher threatening a failing grade. Just you—and whatever willpower you can scrape together on a Tuesday night.

That’s the bad news.

The good news? You don’t need more willpower. You need a system.

Here’s how to stop breaking promises to yourself and start actually hitting your deadlines.

1. Find Your "Why" (And Make It Hurt)

Deadlines don’t work unless you feel them. And I mean deep-in-your-gut, keep-you-up-at-night, can’t-ignore-it kind of feel.

Ask yourself two questions:

1. What am I moving towards? (What’s the payoff?)

   
   

2. What am I running away from? (What’s the pain I refuse to live with anymore?)

   
   

When I launched this newsletter, I was desperate for freedom. I wanted control over my time, a creative outlet, and the chance to connect with people who actually inspired me—not coworkers who threw around buzzwords like “synergy” and “value-add.”

But here’s the part that really hurt: I was trapped. Stuck in corporate politics, buried in endless meetings, pretending to care about projects that made me feel dead inside. The thought of spending another year like that? It terrified me more than the risk of failure.

Your “why” has to hit you like that.

It has to be the thing that drags you out of bed when you’re exhausted. The thing that keeps you moving forward even when you’d rather quit.

Because if it doesn’t hurt enough to stay where you are, you’ll never push hard enough to get where you want to be.

2. Set a SMART Goal and Track It

Goals that aren’t specific are just daydreams.

A SMART goal is:

• Specific: Lose 10 pounds. Launch a website. Call your mom.

  
  

• Measurable: Numbers don’t lie.

  
  

• Achievable: Stretch goals are great. Fantasy goals? Not so much.

  
  

• Relevant: Does this align with what actually matters to you?

  
  

• Time-bound: No deadlines = no urgency.

  
  

For example: “I’ll lose 10 pounds in 7 weeks by going to the gym 4x per week and tracking my meals.”

If you can’t measure it, you can’t manage it.

3. Pay to Play

Want to guarantee you follow through? Put your money where your mouth is.

When I started my real estate investment firm, I was miserable at my job—working long hours for someone else’s dream. I knew I needed a way out, so I spent more than three months’ salary to join a group of high-performing investors.

It wasn’t easy. Watching that kind of money leave my account felt like a punch to the gut. But it gave me skin in the game.

It taught me the right way to approach the business. More importantly, it brought me my very first partner on an apartment deal—someone I wouldn’t have met otherwise.

That investment didn’t just pay off. It changed everything.

Paying upfront forces you to commit. Whether it’s a course, a coach, or a networking group, putting money on the line means you’ve got something to lose—which makes you far less likely to quit.

4. Break It Down (And Block It Out)

Big goals are overwhelming. Small, bite-sized tasks? Totally manageable.

For example, if you’re starting a business, don’t think about the entire company. Focus on the first step: opening a bank account, forming an LLC, or registering your domain.

Then, schedule each step on your calendar.

Forget to-do lists. If it’s not on your calendar, it’s not real.

5. Make It Public

Accountability is magic—and terrifying in the best way possible.

You see, you are far more likely to follow through on a goal when other people know about it. Why? Because you don’t want to look like a liar, flake, or quitter.

Public commitments tap into our primal need to save face.

So, tell your friends. Post it online. Hell, tattoo it on your forehead if you have to (okay, maybe don’t go that far).

If you need an extra kick, use a tool like StickK. You set a goal, create stakes, and designate a referee to keep you honest. The twist? If you fail, your money goes to a cause you despise. Imagine skipping a workout and funding a group you absolutely can’t stand.

Accountability works because it forces you to put skin in the game—social, financial, or both. You stop seeing your goal as optional and start treating it like a promise you can’t break.

And here’s the best part: Every time you show up and follow through, you build momentum.

Momentum turns into habit.

Habit turns into confidence.

So, who are you telling? And what’s at stake if you fail?

Make it public. Make it count. And watch how fast things change.

Why Most People Fail

Here’s the problem with deadlines: they erode.

You miss one, so you push it back. Then you lower the bar. Then, before you know it, the thing you wanted to do has faded into the background, collecting dust like the guitar you swore you’d learn to play.

It’s not your deadline that needs fixing. It’s your system.

Spend more time upfront creating structure, and you’ll spend less time feeling like a failure.

Final Thought

Deadlines turn dreams into reality—but only if you stop treating them like suggestions. Stop procrastinating on yourself. The world is waiting.

Deadlines are powerful—if you respect them.

But respect doesn’t come from willpower or motivation. It comes from systems.

Find your why. Write your SMART goal. Put some money on the line. Chunk it down. Tell someone who will actually hold you accountable.

Your deadlines deserve better. And so do you.

Until next time, ✌️

Ben

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