How To Overcome The Obstacles That Are Stopping You From Chasing Your Dreams

Updated: November 7, 2023

What are your dreams? What are the big goals that you’re hoping to achieve in your life? When you’re alone and imagining your future, what do you see yourself doing?

I asked these questions to a few friends, and I got different answers.

Some mentioned working on their dream job, while others are running their own business. There were a couple who will pursue their passion for travel, while another one wants to write a novel.

Different their responses may be, there was one thing they all did after giving their replies — they paused and smiled.

I can only assume that they suddenly had a vision of that future. They imagined themselves at that moment when they’re finally living their dreams.

To help them come back to reality, I then asked them, “So what are you doing now to make those dreams come true?”

Suddenly, I get a list of reasons, most of which sound like excuses.


They’re not sure if they really want it.

Michael is a college batchmate and works in a construction company. His dream is to put up his own engineering firm someday.

I asked him how he’s preparing, and he mentions that he’s too busy at work so he hasn’t had time to plan for it.

I suggested that he should at least, start nurturing his entrepreneurial mindset. Read business books perhaps, or begin growing his network of suppliers and potential clients.

He agreed with a hesitant voice and then confessed that he’s actually not sure if that’s what he wants anymore.

Being the big boss of his own firm was his dream in college. He’s been frequently vocal about that goal to his family and closest friends ever since.

But now it seems that it’s just his pride that wants that dream to come true. He’s afraid to disappoint everyone, so he’s choosing to disappoint himself.

“Pretend that you don’t care about anyone’s opinion of you, what would you do instead?” I asked.

“I’d support my wife’s dream and work with her in putting up our own restaurant,” he softly replied.

Too often, we pursue dreams that are no longer meaningful to us simply because we’re afraid of what other people will say. Sometimes, and even worse, we just don’t want to disappoint our parents or loved ones who have those dreams for us.

If people can change, then their goals in life can change as well.

It’s normal and it’s okay to let go of your long-held dreams in place of new goals that reflect what you desire now.

They’ve forgotten the reason why they want it.

Larry is a blogger friend who now works in a digital marketing agency as a graphic designer. His dream is to have a web design and development company.

Likewise, I asked him how he’s pursuing his goal, and he confidently answered that he’s doing it slowly but surely.

Coincidently, another friend, Carl was hoping to start blogging and was willing to pay someone to create and set up his website, as he has no web background and technical knowledge.

I introduced him to Larry, who took on the job. He finished Carl’s blog within a few days and became a few thousand pesos richer.

“Thanks for the sideline. I enjoyed it and reminded me why I wanted to put up my own business,” Larry said to me.

It’s a guarantee — pursuing your dreams will entail a lot of planning, research, and boring tasks. Because of these, it can feel overwhelming or too much of a chore that we unconsciously procrastinate.

Sometimes, we rationalize our inaction or delay by saying that we’re taking things slow. But in fact, we’ve lost touch with the passion which gave birth to that dream.

Reignite the fuel by remembering the feeling you had when you first decided to work on that goal.

Find activities that will keep you inspired and hooked on that dream. Reminisce your excitement and create a vision board to motivate yourself daily.

Personally, joining communities of like-minded individuals helps a lot. That’s why I introduced my friend to a group of solopreneurs, so he can learn, share, and network.

They don’t believe they can do it.

Richard and Ana’s dream is simple — to have more time with their kids and go on out-of-town family vacations every few months.

However, with huge household bills, loan mortgages to pay, and their children’s future to think about, they’re stuck with the belief that they can’t afford to travel.

I asked them if they ever did financial planning, and they confessed that it’s too complicated for them and they’re not really good at numbers.

I offered to guide them, and it wasn’t long when they realized that it’s not as difficult as they thought it was. Now, they’re planning to go to Boracay by early next year.

Whether it’s pursuing a small goal or going after a huge dream — never commit the mistake of judging yourself before you even started. Don’t allow negative assumptions to paralyze you.

List down the reasons why you believe your dreams are impossible to achieve, then counter them with concrete measures. You’ll be surprised how easier it is to focus on a solution rather than overthinking a problem.

If you need to acquire new skills, then find out how you can learn that. If you need help, just ask around and someone will answer. Break down your goals and take small steps if you must, but keep moving forward.

Moreover, if you need to sacrifice your free time, personal comfort, or money to pursue those dreams, then simply ask yourself if it’s really worth it — more often than not, it is!


They’re too comfortable.

Michelle is an accountant who dreams of someday owning several pieces of real estate and living off the rental income. It’s an excellent goal, but she’s hardly doing anything to make it come true.

Currently, she has a steady list of clients. She has a fun circle of friends. And she has enough income to afford the luxury of frequent shopping and international travel.

That’s why I believe the reason she’s procrastinating is that she’s become too comfortable, and she doesn’t want to change her routine.

Going into real estate isn’t as simple as buying an apartment or a condominium. It requires property management skills, as well as getting acquainted with the business, social, and legal aspects of running a rental business.

I asked her if she really wants to pursue real estate and I’m convinced that she does. She even tells me that the only accounting she wants to do when she retires is her own and not anyone else’s.

So it seems that she only needs to reframe her mindset and muster the courage to get out of her comfort zone. She needs to make her dreams a priority.

If you’re in the same situation as her, a simple way to remedy this is to list down everything you’re doing during your free time. Then create a second list that enumerates all the tasks you must do to achieve your goals.

To manage your discomfort level, just replace one or two items from your first list with a few items on your second list.

See how the small change in routine feels, and repeat the process. Your dreams will be within your reach sooner than you think.

In Summary

Everyone has goals and dreams, but not everyone makes decisive action to pursue them. Reasons vary, but more often than not — those reasons are mere excuses.

Instead of facing these obstacles head-on, some will choose to hit the snooze button and stay in bed.

Don’t hit the snooze button. Wake up, get up, and chase your dreams.

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  1. Very true, as an OFW, I dream of becoming an entrepreneur and be with my family soon. And I already started by having an online business, and earning part time, from my websites and affiliate marketing, and I also want to teach other OFW and fellow Filipino how to start their own online business too. Thanks for this.

  2. We love how your casual questions to friends turned into a teaching moment for them and now your blog readers. I believe my Beautiful Bride could have started the sane business we have today many years ago and allowed profits to compound through reinvestment. She is however, SO risk adverse that not even a few spare peso would be used to test her idea. I fully understand why a single Mom would have such a high value on any small reserve but I also know for sure that she very much underestimates her skill at seeing oppertunity and writing a great business plan.

    After we were married and started discussions on what would be great business ventures for us, her written plan that lay dormant for many years was one of several on the table. My wife was floored when I said honey, here is two thousand US Dollars, go run a test and let’s see what happens. My thinking was, even if the whole idea failed, because of the through planning, most of if not all of my risk capital would comeback. If not, our bills would be paid and we would still eat. Well, that test run became our first business. It was only a matter of months when Beautiful Wife blew well past her first income goal. We have NEVER regretted or looked back !

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