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50 Ways to Overcome Obstacles to Your Success

Are obstacles interfering with your success? This blog lists 50 ways to overcome obstacles to your success!

Are you ready to live by your own rules? Trouble is, many of us still live by rules that others made—ones that don’t work well and actually keep you from happiness and success. So, you need to change habits that no longer work for you. Use these 50 mind-hacks to replace your old habits with a whole new way of thinking geared to propel you towards your goals and successful life.

Table of Contents

50 ways to overcome obstacles to your success

Use Affirmations Effectively

If affirmations don’t work for you, consider the fact that you may be investing your energy and hope into (a) unrealistic ones you don’t really believe in or (b) generic affirmations that are too vague and broad-ranging.

The key to making affirmations work is two-fold:

  • Be specific. Take your affirmation from pie-in-the-sky platitude to something you can achieve
  • Make sure you believe in the message at a gut level

Anyone can say: “I am a millionaire right now,” but that is not really an affirmation—it’s wishful thinking.

On the other hand, telling yourself daily: “I have a millionaire mindset” can be a powerful boost to your confidence and outlook, if you pair it with a plan of action.

Change your Glass

Are you a “glass-half-empty” person? If so, call yourself on these negative, doom-and-gloom self-messages. Say, “Oops, that’s a glass-half-empty thought. Let’s turn this around and transform this thought into glass-half-full.”

It may feel contrived and your heart may not be in this little exercise at first, if you’ve been undergoing stress or challenges in your business or personal life—but if you persevere, you will soon discover that deliberately changing glass-half-empty thoughts to glass-half-full ones increases:

  • Gratitude
  • Empowerment
  • Optimism
  • Proactivity
  • And ultimately—success!

Cut Toxic People Out of Your Life

Toxic people can be an obstacle to your success. As human beings, we can’t help but be influenced by what the people around us say and do. Inevitably, toxic people come into our lives—people who drag us down instead of building us up (or at least, not harming us!) To overcome obstacles such as toxic people, if someone drains you of energy, makes you lose confidence or feel worse about yourself, limit or eliminate contact.

This is easier said than done, since we all want to be loved or at least liked. Try applying a checklist. Ask yourself:

“Does that person…

  • Talk only about themselves?
  • Focus solely on what I can do for them?
  • Make me feel stressed or heavy at the thought of interacting with them?
  • Suck me into a negative mind-frame?
  • Make me doubt my abilities?”

If you answered yes to even one of these, time to either change your responses—or cut the cord.

Reframe Negative Thoughts

The damage may be done. A negative family environment or significant relationship has left you with poor self-esteem or poor processing habits. Or perhaps it was that toxic company you worked at for twelve years.

But no matter what caused you to adopt an “I’m doomed, I may as well give up: Happiness/success is not for me” head space, you can make the decision to change that—starting today.

One successful technique that psychologists use is called “re-framing”. Here’s how to do it:

  • Take a negative, habitual thought
  • Filter it in an objective manner through the light of reality
  • Replace your negative thought with a positive but realistic, corrected version

You can do this with any type of thought—business or personal. For example, change “I always screw up” with: “I don’t always screw up. Sometimes I make mistakes, like everybody else—but I learn from them.”

Avoid “All-or-Nothing” Thinking

A particular type of highly destructive self-talk is known in psychological circles as “all-or-nothing thinking.” This type of thinking can be an obstacle to your success. To ensure you don’t do it, watch out particularly for the words “always” or “never” in self-talk: For example, “I always fail at everything I do” or “I’ll never learn how to do split-testing.”

All-or-nothing thinking is just another way of beating yourself up, and strips away both personal power and confidence.

To overcome obstacles such as cognitive distortions, if you catch yourself making an all-or-nothing statement, reframe it instantly to a more realistic, empowering thought. For example, “Lots of people learn how to split-test effectively: I can choose to outsource this or I can just take my time, read instructions more carefully—and do it till I get it right.”

Avoid Catastrophizing

Are you a catastrophizer? Is every setback that happens the end of the world?

Catastrophizing is just another form of beating yourself up. Even if you do experience a disaster—for example, a power outage occurs and you lose a graphics file you’ve been working on for hours—realize that in the large scheme of things, this is frustrating but not really the end of your world.

Instead, treat it as a learning experience. For example, “Next time I’ll remember to save that graphic at every step.”

Ask Yourself: “Will This Matter in Five Years?”

One of the best ways to train yourself out of a doom-oriented, catastrophizing head space is to get into the habit of asking yourself, after each disaster: “Will this matter in five years?”

If the answer is “no, I won’t even remember it,” it’s not worth getting in a knot over.

As wildly successful entrepreneur E. Joseph Cossman once said: “If you want to test your memory, try to recall what you were worrying about one year ago today.”

Set a Limit on Worry Time

If you are a chronic worrywart or a particular task or event is causing you to worry, table it. This type of thinking can be an obstacle to your success. To overcome obstacles such as excessive worry, set aside a specific time to worry. For example, “I’m going to think about this from 10:15 a.m. to 10:40.” Then when you start to fret about it, tell yourself, “It’s not worry time yet—I’ll put that aside till later.”

Realize that Fear is Just Excitement

You may have “learned” that the butterfly-sensation in your stomach before you give a presentation or webinar is fear. Try reframing that learning to: “Wow, I’m excited about this!”

Changing fear into excitement in your mind is the first step to taking action, taking risks—and succeeding.

Recognize that Feelings May Follow Actions—Not Precede Them

Most people give up too easily when they are attempting to change mental habits. This happens because they expect their feelings to change instantly.

The more negativity or powerlessness is ingrained in our habitual thoughts, the longer it takes to “break” that response. Go through exercises such as reframing anyway and one day before too long, you’ll find your feelings will eventually follow.

See Failure as a Learning Opportunity

This is no trite platitude. The most successful entrepreneurs aren’t the ones that instantly succeed. Rather, they are the ones that rebound, take notes of what didn’t work, brainstorm—and keep going. True failure is never trying in the first place.

Focus Outward

Our worst worries, fear and paralysis behaviors and mindsets occur when we are focused inward—on ourselves.

Focus outward instead. Focus on how you’re going to help the person you are writing that eBook for or how much it will help not just your client but other members of his team if you get your project in on time.

When we are focused on helping others, there is no room for worry.

Find your Passion

Even if you’re stuck in a business you can’t instantly get out of, look for what you are truly passionate about within it. What in this current business makes time fly, instills you with vision and confidence, and brings satisfaction?

Find a way to tap into that. Tweak your routines, outsource energy-draining tasks—and most important, adjust your overall business plan so that you are more closely following the path that inspires you towards your success goals.

Realize that You are Already a Success

Think about all the things you have already accomplished, all the times you have already picked yourself up and dusted yourself off.

And if you’ve unsuccessfully tried business model after business model, don’t be discouraged. You’re in the company of truly great entrepreneurs like Oprah, Sir Richard Branson and Ariana Huffington.

Even if you have a string of failures behind you, this only means you’ve already proven you have the Number One trait of all truly successful people: Tenacity. You never give up.

So keep on keeping on—and congratulate yourself for being on the right track.

Avoid Analysis Paralysis

Did you know that over-preparing and over-analyzing can be another form of procrastination—or at the very least, avoidance behavior? Especially if it is stopping you from branching out or taking any sort of risk.

To overcome obstacles such as analysis paralysis, get into the habit of setting cut-off dates. For example, “On Tuesday the sixteenth, no matter how unprepared I feel, I’m just going to launch this website.”

Giving yourself a definite cut-off date and making a commitment to stick to it can help focus your thinking and spur you into action.

Beware of the Feedback Loop

Are you addicted to collecting feedback and opinions before taking each step?

Do you ask everyone in your family, members of your Facebook Group and the membership site you belong to? If you added “the mailman, my hairdresser, my son’s two best friends and the family dog”, the answer is definitely “yes!”

This type of thinking can be an obstacle to your success. To overcome obstacles such as feedback loops, cut this number drastically. Pre-select only the people who have given you professionally-valid and knowledgeable advice: Who can be honest without cutting you down—those who provide constructive criticism you can use to improve, rather than those who complain or make you feel like they’re taking over your project.

Asking too many people indiscriminately for feedback can actually signal a huge lack of confidence. Limit the number to under half a dozen—and chose them with care. Think “accountability partner” more than “feedback provider”.

Cultivate Self-awareness

Being self-aware doesn’t mean beating yourself up or giving yourself negative messages. It means assessing yourself as objectively as you would assess any other person or idea.

Get into the habit of asking yourself questions like:

  • What am I doing well?
  • What do I have trouble with?
  • What could I do better? How?
  • What am I doing too much of?
  • How do my colleagues see me?
  • How do I see myself?

Done properly, not only can this help you succeed—it’s also fun as you uncover each possibility.

Learn to Develop Radar

This is a particular component of the self-awareness process. “Radar” occurs when a little alarm bell goes off in your brain or gut, telling you that something is either wildly exciting and therefore full of potential/right for you… or completely off-kilter.

Most people are so caught up in worry or activity that they ignore these barely-noticeable frissons—but these as invaluable micro-clues to staying on course for success.

Be Secretly Organized

Setbacks and curveballs rarely rattle the organized because they have set in place systems and habits to deal with every eventuality.

For example, these are the entrepreneurs who always have a “signature” presentation in their pocket for last-minute emergency fill-ins, who employ strong teams to watch their backs, who always leave early to get to events on time, who create plans and follow them—while building in flexibility, so they can “go with the flow.”

Being organized doesn’t mean scheduling yourself down to the last second of your day. It means being prepared for more than one scenario and giving yourself the freedom to think on the fly.

Act on the Short Stuff

Reduce overwhelm by doing any task that is going to take less than five minutes immediately. You’ll feel much more relaxed and accomplished by the end of the day.

Change your Environment

Getting tired? Feeling stale? If so, try changing your environment—not just by going for a walk or doing a little gardening, but physically taking your work to another location. Work on the patio during summertime. Try an internet café during colder seasons.

And if you’re doing heavy research—base yourself in your local library. Not only will your mind be stimulated by the change of scene, you’ll have extra resources at your fingertips.

Know your Triggers

If you find yourself procrastinating, don’t worry so much about the cause: Find your triggers. What sends you into Avoidance-Land? Is it a particular topic you have to write about? The fact that you hate bookkeeping or cleaning house? A particularly unpleasant client? One that reminds you of that scary fifth grade teacher?

Sometimes when we identify causes and triggers, we are able to deflate the bogeyman. “Hey, I’m not ten years old any more. So what if this client talks like her?” And there are other actions you can take. For example, hire a cleaning lady once or twice a week if you hate housework or outsource your bookkeeping to a bookkeeper.

To overcome obstacles such as triggers, recognize and name a trigger to take away its power. We then feel empowered to make proactive choices and deal with what is making us want to put off a task or responsibility.

Reward yourself

This isn’t a new concept—yet too many of us seem to forget about it due to worrying and focusing on necessities.

The most successful people, however, know how to enjoy the perks of any lifestyle.

Choose yours carefully and fit them in. So you can’t afford a weekend at a luxury resort right now—but maybe you can invest in a “reading afternoon” or a bunch of fresh flowers every weekend.

When you see tangible evidence of your hard work bring about a reward, it is much easier to feel balanced, accomplished, happier—and more confident. So consider this a necessary investment!

Upgrade your Office Space

You’re used to working with your laptop at the kitchen island, because that way you can keep an eye on the kids—except that the kids are a lot bigger now and you don’t really need to keep an eye on them. Or you’ve been typing in a corner of your bedroom, keeping your partner up at nights. Or any one of the “temporary” scenarios people lock themselves into.

If you don’t have a spare room or an office, prowl around the house and get creative. What about that spot under the stairs? Or the alcove in that over-roomy upstairs landing?

Create a dedicated office; and if you already have one, clear out and upgrade the space you have. Investing in as professional a layout as possible will make you feel more professional—and increase your productivity.

Set Ground Rules—for Yourself!

If you constantly find yourself reactively responding to family or friends who don’t seem to understand you are working, set ground rules – not just for your nearest and dearest, but also for yourself. For example, set work hours and tell the worst offenders you won’t be available during that time period every day. Then respect your own rules if they call or drop-in.

Don’t answer the door. Don’t pick up the phone if you see their names on Call Display. Don’t answer emails or Facebook PMs.

If you stick to your guns, they will eventually realize you mean what you say. But if you make exceptions, you’ve only yourself to blame when they turn up on your doorstep during work hours. If you don’t respect yourself, others won’t!

Identify your Weak Points—and Plan Around them

Knowing your weaknesses is the first step to managing—and overcoming—their negative effects. To overcome obstacles such as your weakness, tThe key is to identify them without judging yourself harshly.

For example, if you know that you will procrastinate all day if you start the morning with Facebook, rearrange your schedule so that you do an hour of solid work first before checking your Facebook feeds.

Break it Down into Bite-sized Chunks

This is especially true for any task that overwhelms you or makes you procrastinate. If the thought of writing a thirty-page eBook has you running to clean the silverware, just so you won’t have to face it, then break that task down into baby steps.

Set daily goals that are easily manageable, no matter how overwhelmed you feel. For example, writing 500 words a day, or one page a day.

Use Apps, Schedulers and Timers to Help Manage your Workload

Find out where you need help, and use apps, schedulers or timers as memory prompts or incentives to help you manage your workload—as well as important life tasks such as: “Take morning pills!” or “Time to drink another glass of water.”

Learn to Delegate

Make the most of family, friends and employees who love to do tasks you hate. Delegate tasks that drain your energy.

And don’t forget to thank and reward those who help you out.

Plan for Outsourcing

No one can do everything, even though many people pretend they do. Top performers always have top teams of fellow specialists to whom they delegate or outsource non-money-making tasks. And you can outsource personal life tasks too!

Honor your Learning Style

Sometimes the reason we find tasks so difficult or find that systems others praise just don’t work for us lies in the fact that we have a different learning style. Lists may not work for you if you are a visual or auditory learner. In that case, dictate things-to-do into an audio file or use colored highlighters to highlight your top three priorities.

Drastically Trim To-do Lists

Speaking of lists, we tend to put too many items on our daily to-do lists; then get discouraged and disheartened when we continually don’t accomplish most of them.

To overcome obstacles such as long to-do lists, from now on, focus only on your top three priorities. Don’t add any more tasks until you’ve finished those three. After that, it’s totally optional!

And recognize that if you get a minimum of one mega-important task done per day, you have legitimate grounds to celebrate!

Walk Away from the Computer

Did you know that a percentage of people who spend hours a day at the computer without a break develop serious, life-threatening or highly unpleasant physical problems, such as deep-vein thrombosis or pilonidal cysts at the end of the tailbone?

Taking a break not only helps bring oxygen to cells and restore circulation to the body, however, it also helps refresh and clear the mind. Try going for a brisk, ten-minute walk a couple of times a day. Or get up and do stretching or yoga exercises.

Your body—and your mind—will thank you.

Drop the Hours-for-Dollars Business Model

If you’re a business owner, don’t spend day after day trading hours for dollars.

Instead, get into the habit of analyzing daily how you can convert your knowledge and work you’ve already done into self-regenerating income.

Hours-for-dollars breeds reactivity. Learning how to repurpose work you’ve already done and turn it into self-regenerating income leads to proactivity, giving you time to plan for and create the freedom you crave.

Adopt a “Motto of the Month”

Set a big but achievable goal for each month. Find a quote or motto that sums up what that goal is all about. Print out or write your motto for the month and pin it up in a visible spot. For example, over your desk.

Refer to it often, and repeat it to yourself aloud at least three times a day.

Adopting a motto related to your main monthly goal can help keep you focused and on target—as well as inspired.

Be Grateful for the Small Things

To overcome obstacles such as feelings of overwhelm and pessimism, get into the habit of starting your morning out by choosing three things you are grateful for that day and naming them aloud—no matter how basic or silly these three things may be.

Smile when you say, “Today I am grateful for…”, even if you don’t feel like it. Smiling will help shift your mindset and raise your energy.

Ask Yourself What you Want to Remember About Today

Another way to get focused very quickly in a positive way is to decide what you want to remember about today.

What is really important about this one day in time, which will never come again.

If you focus on this sincerely, and do it, the results may surprise—and uplift—you.

Hang Out with Positive People

There’s a second part to getting rid of toxic people in your life: Actively replace them positive people instead.

If you rid yourself of the overly-critical or doom-and-gloomers, you’ll quickly find yourself attracting more of the same type if you don’t seek out positive people to connect with.

To overcome obstacles such as negativity, hang out with positive people who will raise your energy and vibrations. The, toxic people will no longer be attracted to you.

Learn to Like Yourself

In addition to waking up every morning and counting aloud three things you feel grateful for, name three things you like about yourself.

Try these two little exercises for a month, and see what a difference it makes to your mood and confidence level.

Ask Yourself Positive, Proactive Questions

To shift to a more proactive, self-empowered headspace, change your self-questioning openers to “what” and “how” rather then “why.”  For example, Change “why can’t I figure out this camera?” to, “What do I need to do, to make sure I learn and remember the most useful settings?”

Understand Why You’re Still a Perfectionist

Ever wondered why you can’t lose your perfectionist ways? Most likely, you had a parent or teacher who drilled it into you that perfectionism was next to godliness. This is an underlying conviction you may not realize you’re stuck with.

To overcome obstacles such as perfectionistic thoughts, give yourself permission to acknowledge that this way of thinking is actually a cognitive distortion. Doing your best doesn’t mean it has to be perfect. So, don’t re-write that book or spend days on that four-hour project—just finish it and let it go with your blessing.

Follow the WTWTCH Formula

Are you afraid to take risks? Do you have “roadblocks” that are limiting your potential? For some, it can be a fear of public speaking. For others, getting on a plane to go to that convention. It can even be as small as not asking a question that you’d love to ask.

Instead of concentrating on your fear, ask yourself, “What’s the worst that could happen?” Once in a blue moon, yes, you’ll realize that things are definitely risky to the point of death-defying—but more often than not, the answer is something like, “Well, I might gain new networking contacts if I go to the convention.” And if your answer is something like, “What if no one will notices me,” you can plan to make sure that they do!

Stay Connected

There’s a tendency among those who work at home to become accidental shut-ins. But humans are social animals. So, it’s important to make connections and stay connected—not just in your social life, but in your business life too.

Schedule a weekly or monthly meeting via Skype or Google Hangouts, so that your team can get to know each other as human beings.

And if you’re a lonely VA, join or create a support group for VAs. And don’t forget to get together in real life, whenever you can.

Having the feedback and company of others not only helps us find answers to questions, it sandpapers our rough corners and helps us realize who we are in connection to our world.

Use the Twenty-Minute Rule for Power Naps

Got a huge project that you really must push through to finish? No time for sleep? Set your alarm for twenty-five minutes and take a power nap. Five minutes to fall asleep; twenty for the nap.

The popular TV show, Mythbusters, tested the concept of napping extensively. They tested mental alertness in people who had no sleep, longer naps and twenty-minute power naps. The twenty-minute group performed the best, every time. So if you’re a human being and you really do have to “push through” a long day or project—take that twenty minute power nap for maximum efficiency.

To overcome obstacles such as feelings of exhaustion, try a power nap.

Lose the Word “Should”

There was a saying back in the nineties: “Don’t should on me, and I won’t should on you.” And it’s still as relevant today as it was then.

“Should” is a word all about powerlessness. It’s soaked in guilt, regret, and failure. It’s all about making yourself do what you actually hate doing and often what others think you “should” do. And that’s not what success is all about.

To overcome obstacles such as limiting beliefs, throw the word “should” away if you want to feel happier. Either do it—or don’t. But don’t waste time on regrets.

Drop Three Things per Day

We talked earlier about focusing only on three top priorities. Now, take that one step further, and look for three things it would be a relief to drop every day.

  • Don’t want to check out that eCourse you bought six months ago? Delete it!
  • Struggle over creating graphics? Outsource them.
  • Hate to do housework? Hire a cleaning lady.

And, of course, some tasks you can simple afford to just stop doing altogether!

Narrow your Focus

To overcome obstacles like being overwhelmed by distractions or multi-tasking, try focusing only on one single task or responsibility at a time, ignoring everything else. Tip: Use a timer—and keep your time periods no longer than twenty or thirty minutes.

Nurture Your Relationships

If you want to be truly in touch with life, don’t lose touch with the people that matter to you. Make time for close friends. Remember to thank and appreciate your team members. Begin and end the day by hugging and kissing your spouse and your children. And if you don’t have any humans to hug, be sure to make time for your dog or cat!

Truly successful, happy people aren’t all about work. They know the importance of nurturing and maintaining the relationships that make all that hard work worthwhile.


Listen to your friends. Listen to your loved ones. Listen to your colleagues—and especially to those on your team.

Make notes of things that strike you. Follow up on things promised or concerns expressed.

To overcome obstacles such becoming too self-focused, the most successful people know how to listen—and follow through.

Create More of What you Want

Every time you find yourself particularly enjoying something—anything at all, from taking a simple but refreshing nap every afternoon to the adrenalin rush of sealing a six-figure deal—get into the habit of asking yourself, “How can I create more of this?”

In order to create more of something, you need to let go of something else. So, the second part of this question is, “How do I get rid of …?”

In order to create more of what you want, you need to focus on it, live it, breathe it—and plan for more. It doesn’t just happen on its own. So go after what you love—and what makes you feel excited to be alive.

In sum, realize that these mind-hacks are not something you “should” do. Pick and choose, adapting them to your personality, goals, and circumstances. They are here for you to pick up and use, like instruments, so you can fine-tune your professional aspiration and your life to finally create true happiness and success.


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