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36 Ways To Challenge Yourself In 2020

Sometimes we need to reboot our lives, much like restarting a frozen computer screen when nothing else will fix the problem. When we’re feeling wired and tired, we can slow down long enough to ask ourselves, “Is this depression or depletion?” Frequently it’s the latter.

When we’ve been burning the candle at both ends for too long, things can get jangled up. We become forgetful. We snap at our family over inconsequential issues. The very thought of merely taking out the garbage feels overwhelming.

At such times, it can help to (1) take a step back from our lives, (2) get off auto-pilot, and (3) challenge ourselves to try things a different way. When we make the effort to live intentionally rather than doing things the ways we’ve always done them, new possibilities open up.

As human beings, we share an inherent need to grow and change. Remaining stagnant goes against our very nature and can lead to despondency, boredom, and anxiety. Ironically, while the thought of getting out of our comfort zone can invite anxiety, actually taking those unfamiliar steps can invigorate and relax us.

Have you ever agonized and procrastinated over a work or school project, alternating between feeling exhausted and feeling edgy at the prospect of tackling the endeavor? Yes, I have, too. Then, how did you feel once you actually took the bull by the horns and got the job done? Did you feel relieved? More self-confident? Have a renewed burst of energy? Any and all of these are common reactions to pushing yourself a bit.

The following are examples of healthy challenges for you to try, to remind yourself through your actual personal experience (rather than mere conjecture) of what you’re capable of, what you might enjoy if given the chance, and how many options for happiness and fulfillment stand before you, just waiting to be realized. Some challenges are more daunting than others, so it’s up to you whether you’d rather jump in the deep end or ease your way into the water.

  1. Jot down five things you love about yourself. These could be your sense of humor, your tenacity, your honesty, your love of animals, your skill at baking… anything at all. If nothing comes to mind, keep digging.
  2. Work on a crossword puzzle. As in life, the clues in these puzzles are not always what they seem, which prompts you to look at a problem in different ways and with various interpretations.
  3. Use your non-dominant hand. If you’re right-handed, try eating a meal with your left hand, for instance. If you’re a leftie, brush your teeth with your right hand. This is quite a workout for your brain and also keeps you focused on the task at hand.
  4. Take the stairs rather than the elevator or escalator. This not only strengthens your cardiovascular system and your muscles, but you might run into a coworker or neighbor.
  5. Create a morning routine that works for you. This could mean preparing a healthy breakfast, taking time to read the news, meditating, walking the dog, or going to the gym. The point is, know what’s most effective for you, specifically, and make it a regular part of your life.
  6. Have a face-to-face conversation rather than texting or IM-ing. So much can be misconstrued when communicating electronically. In addition, when we’re in someone’s physical presence, we can pick up on their facial expressions, vocal intonations, and body language, as can they with us, and we feel closer to them.
  7. Initiate a conversation with a stranger. While doing errands or standing in line at the grocery store, don’t close yourself off to other people by staring at your phone or blankly off into space. Instead, simply say hi to someone, ask them how their day is going, or comment on the weather. Even in a big city, so many people feel isolated. You could make someone’s day just by acknowledging someone’s existence and giving them a smile.
  8. Give yourself a pat on the back. Pay yourself a compliment. We talk to ourselves, either out loud or mentally, throughout our lives. Make an attempt to include encouraging comments in this dialogue with yourself. In fact, smile and say “I love you” to your reflection in the mirror.
  9. Take a yoga class. While you’re at it, embrace the yoga principle of being present in mind as well as body, and of accepting where you’re at today physically, emotionally, and mentally. Don’t push yourself to the point of injury, and don’t compare yourself to other people, or to yourself as you were yesterday or last month.
  10. Give someone else a pat on the back. We all need encouragement. Be that person who brightens someone’s day by pointing out something admirable or endearing about them. We can make such a difference in this world simply by reaching out and being kind. Sure, you’re putting yourself in a vulnerable position, but it’s worth it.
  11. Prepare a meal at home. Now and then (or more often), resist the urge to order take-out, pick up fast food, eat a protein bar, or dine at a restaurant. Use your meal prep time to practice being present, listen to upbeat or soothing music, or just focus at the task at hand. Appreciate yourself for taking the time and making the effort to take care of yourself.
  12. Take a walk around the block. Doing so can help to clear your mind, get your circulation going, lift your spirits, and allow you time to get in touch with your feelings.
  13. Have an intense workout session. Exercise not only benefits our physical and emotional health in numerous ways.
  14. Spend at least 30 minutes reading a book. Challenge yourself to stay focused. Consider what you’ve learned or appreciated about the process.
  15. Doodle. Let your creativity and imagination take over. Don’t worry about the results – your doodles are simply for you to play a bit.
  16. Visit a museum. Try and enter into the worlds of the artists. What would it have been like to live at that time? How are you affected by what you see and experience?
  17. Visit a park, to people-watch or just relax and enjoy the natural setting. Notice the trees, flowers, birds, and other creatures.
  18. Declutter your home and office space. Visual clutter can scatter us mentally, so streamlining your physical surroundings can reduce anxiety.
  19. Donate clothes you haven’t worn in the past year or so. Why take up extra space in your closet, when someone else can benefit from your unused garments?
  20. Read inspirational works. Listen to a TED talk. Change the background of your computer screen or phone to an inspirational quote or photo. Allow someone else’s encouraging and creative thoughts to expand your own view of the world and the possibilities that lie before you.
  21. Write down 10 things you’re grateful for. In doing so, you shift the focus from what you’re vying for to what you already have in your life. The cup is indeed half-full.
  22. Write down 5 things you’ve learned about yourself in the past year. How have you grown? What changes would you like to make in the next year, based on what you know about yourself?
  23. Make a list of 5 things that you’re very attached to. Ask yourself what purpose they serve. What would happen if you tried giving up one (or more) of them for a day?
  24. Do a random act of kindness. Bonus points if this is done anonymously.
  25. Have a lunch date with a friend. Stay 100% present for your friend (no cell phones), show interest, and learn more about them.
  26. Let go of relationships that are not mutually beneficial. If the two of you are not consistently bringing out the best in each other, it may be time to turn your attention elsewhere. Surround yourself with creative people who see the possibilities in challenges.
  27. Work on your relationship with food. Try out a new restaurant or a new coffee/tea shop near you. Order something new from a restaurant menu. Try a new, healthy recipe. Eat one meal without also reading, watching TV, checking your phone, or any other activity at the time.
  28. Listen to unfamiliar music, or new music by a favorite artist. Pay attention to your feelings. What do you like or dislike about the music? Why? Try to find something of value in the music.
  29. Refrain from complaining – in trying to do so, you may be surprised how much of the time you focus on problems. Instead, notice the good in all situations. At times this may be hard to find, but it’s there.
  30. Watch your language. Similar to #29, look specifically for times when you box yourself in by saying that you’re not good at something or you can’t do something. Add the words “not yet” or “until now”. What’s more, you can positively influence your future by saying “from now on…” You are destined to be hemmed in by your past.
  31. Smile even if you don’t feel like it. Research has shown that our moods often respond to our facial expressions, and that smiling gently (no need to grin broadly) can lift your spirits. In addition, smiling at others can cause a chain reaction, brightening their mood, which can lead to them smiling at other people, and so forth.
  32. Watch the sun rise. This miracle happens every day, yet most of us take it for granted. Witnessing something so awesome can help remind us of our small but meaningful place in the universe.
  33. Take 15 minutes to tackle a chore you’ve been putting off. Set a timer. You’ll be amazed at how quickly the time goes and how much you can get done.
  34. Take a 24-hour break from watching TV and checking/posting on social media. You will find that the world won’t end while you’re unplugged, and you’ll have more energy and time to devote to other things. You might even discover a new interest or have an insight which wouldn’t have occurred to you if your mind was still preoccupied with checking your Instagram page.
  35. Be authentic in all of your relationships and encounters – including with yourself. We create extra tension and strife when we tell white lies, even though it may seem convenient at the time. Strive to be rigorously honest.
  36. Do an inventory of your personal habits, and determine which ones work for you and which ones don’t. Resolve to focus on those which benefit you, and to let go of those which hinder your personal growth.

Whatever you choose to do, set a daily goal – and meet it! Perfection is not the goal here – the attempt and doing your best are what matters\. By challenging yourself to push the envelope on a consistent basis, you’ll gain self-confidence and boost your ability to maximize your potential and happiness quotient.


36 Ways To Challenge Yourself In 2020

Rachel Fintzy Woods, MA, LMFT

Rachel Fintzy Woods, M.A., LMFT is a licensed psychotherapist in Santa Monica, California. Rachel counsels in the areas of relationships, the mind/body connection, emotion regulation, stress management, mindfulness, emotional eating, compulsive behaviors, self-compassion, and effective self-care. Trained in both clinical psychology and theater arts, Rachel works with people to uncover and develop their unique creative gifts and find personal fulfillment. For 17 years, Rachel has also been conducting clinical research studies at University of California, Los Angeles (UCLA) in the areas of mind/body medicine and the interaction of psychological well-being, social support, traumatic injury, and substance use. You can read more about Rachel at her website:

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APA Reference
Fintzy Woods, R. (2020). 36 Ways To Challenge Yourself In 2020. Psych Central. Retrieved on October 25, 2020, from


Last updated: 28 Jan 2020
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