How to Stick to Your Self-Imposed Deadlines

The downside of working on your own is that you postpone the things you’re supposed to do, and your project takes an infinite amount of time to accomplish.

I’d write out the tasks that I want to accomplish and mark the due dates in my calendar. Yet, I don’t meet those self-imposed deadlines and let things slide.

If this also sounds like you, then you’d need a deep look into yourself because if this behavior becomes habitual, it has a negative consequence on your psyche.

Here’s what happens.

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The first thing to acknowledge here is that every time this happens, you are, in a way, breaking promises with yourself. Can you trust someone who repeatedly breaks promises? No. If you do this to yourself, you’re going to lose trust and confidence in yourself and lower your self-esteem.

When you miss a deadline, you might think to yourself consciously or unconsciously, “Oh well, I’ll get it done next time.” But that very thought, if done repeatedly, will negatively affect your sense of identity.

Making daily progress toward your deadline matters not just for the completion of the project but also for yourself.

Equipped with this understanding, here are three things you need to stick to your self-imposed deadlines.

Consequence and accountability

When you stop showing up to work, your boss and your coworkers will notice. They’ll form ideas based on your not working and missing the deadlines. There’s a real consequence for slacking off at work. Aside from the obvious consequence of losing your job, there’s another driving force that motivates us to show up on time. Avoiding public embarrassment.

If you’re a remote or solo worker, what could you do? Use the same psychology against yourself in a different way.

You have to give yourself a sense of urgency and hold yourself accountable.

If you haven’t been doing a great job making promises to yourself, make a promise to someone other than yourself. And tell that person not to let you off the hook. And that person will be disappointed with you if you don’t follow through on your words.

By simply upholding your words and keeping a promise to someone else, you’re more likely to stick to doing the things you’ve set out for yourself.

Tell a trusted friend. Or a rivalry-friend. Even a peer or junior coworker (they’d love to be able to have a chance to boss you around). Get a coach or advisor that you’d check-in with regularly. Announce to your social media followers.

You could use a service like, where you put your money at stake if you don’t follow through on your goals.

You could try where you share your progress with people with the same goal and subscribe to their coaching program.

Get advice from real-world domain experts at Receive advice on your first call. Then schedule another call in advance and implement the advice you got before the next call. is not the cheapest service, but from my experience, the return is worth it.

Being held accountable and having to report about your progress regularly forces me to make progress.

Remind yourself with a progress tracker

You need not just any reminder but a visible reminder.

We all know what we need to be doing. Maybe it’s losing weight, writing a book, or following through with that project idea. Yet, why don’t we take action?

Just knowing what you need to do is not enough. It can’t just exist as a fuzzy thought. You need to be reminded. And the reminder has to be visible so that you can look at it every day.

I used to work for a company that created a mobile app with daily content updates. How did I make sure the app got updated every day? Every morning when I sat at my desk, I opened a spreadsheet calendar that showed what content needed to be updated when.

I do the same with my projects.

For weight loss, I have a calendar that shows which exercise I will be performing. I look at it and remind myself of what workout I did in the past and what I will do next. I have a progress tracker for my other personal projects as well, like my course creations.

Some people write their goals every morning. But be don’t get into the trap of feeling satisfaction from writing your goals. Connect your goals to your daily actions. Unactualized goals are just wishes.

That is why a reminder with a progress tracker works better.

We need to be reminded of the concrete, specific action steps. What did we do yesterday, and what can we do today and tomorrow? Clarity begets action.

If you have a diet goal, keep track of what you eat and how much you exercise. If you’re trying to grow your website or app, look at the traffic analytics. If you’re trying to finish a project, have a checklist and to-do’s assigned to specific dates on your calendar.

Create a progress tracker and look at it every day. Use a spreadsheet or Trello board.

My choice of tool is NeuYear Calendar, a wall calendar that shows all dates and weeks in a year. I write an X in my NeuYear Calendar after every workout session, and it increased my adherence to the schedule.


Courtesy of

Make it a real priority

If you care about losing weight, it has to be your priority. That means you have to jog or eat a healthy breakfast before you open Instagram in the morning.

If you want your side hustle to take off, you have to make that your priority. Work on your side hustle before you begin your full-time job.

If you want to save money, put some money on your savings account before you pay off your credit card bills, taxes, or utility bills.

When you have your priorities straight, there’s no room for doubt. You’re not going to talk yourself out of doing something. If you decide that it’s important to you, then you’d take action, however small.

You have to decide what’s important to you. No project, activity, or goal is intrinsically important or meaningful. But you decide when something is. And act upon your decision.

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About Sushi

Hi, I'm Sushi. I started this blog to share productivity tips and tools to stay organized as a remote worker.

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