Giving yourself permission to want change is a way of acknowledging where you are without judgment. Decide now that it’s going to work out and that you can complete what you’re setting out to do. This is the very first step to believing in yourself — simply entertaining the idea. Spend time thinking about the outcome you truly desire. Get as detailed about your WHY as possible. Imagine how the version who’s in full belief you thinks and feels. Consider what’s different or more expansive about this future version of you. Validate yourself. If you want it, it matters. This essential pre-work creates the possibility of growth and change before even taking action.
Starting something new is scary. Learning to believe in yourself can be a critical precursor to starting a new initiative. Why is it so important to learn to believe in yourself? How can someone work on gaining these skills? In this interview series, we are talking to business leaders, authors, writers, coaches, medical professionals, teachers, to share empowering insights about “How To Learn To Believe In Yourself.” As a part of this series we had the pleasure of interviewing Amelia Pleasant Kennedy.
Amelia Pleasant Kennedy is the CEO + Founder of A Pleasant Solution. Amelia is a Certified Life Coach, Professional Organizer, and Fair Play Facilitator. She helps folks permanently eliminate clutter in their homes and lives by uncovering the root cause of their beliefs around organization, belongings, division of labor within the home, time usage, and productivity. With a keen ability to listen for what goes unsaid, Amelia coaches from a space of total curiosity and non-judgment so that clients build a deep sense of self-trust.
Thank you so much for joining us in this interview series! Before we dive into the main focus of our interview, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?
I grew up in a tiny rural town in West Virginia. I was a strong student, loved classical ballet, playing in the woods, and climbing trees. Being organized, self-disciplined, and timely were traits that were regularly reinforced by my parents and teachers. Leaving West Virginia for Wellesley College was my first big risk, and I’ve continued to believe that any risk I take will reap rewards. I’ve learned to believe in myself by seeing that there’s always a solution to any obstacle.
Two weeks after graduation, I moved to Cape Town, South Africa for two years. My husband and I bought a house, went to graduate school, and I worked at the National Gallery of Art. Collectively, we decided to always follow the adventure. I’ve moved over a dozen times and now have it down to a science. At 6 months pregnant I was accepted into Northwestern’s Ph.D. program in Art History, and my husband was accepted into Harvard Business School. I deferred my program for a year, then packed up our toddler and moved to Evanston for our first round of long-distance parenting and marriage. It was an intense year, yet I knew that attempting my program and parenting solo would build resilience and deepen my belief in myself. My husband and I now have three children, are raising an elite athlete, and are on our second round of long-distance parenting and marriage. Last summer our family lived in and worked from Barcelona.
What or who inspired you to pursue your career? We’d love to hear the story.
In 2018, after having been at home with my children for over a decade, I was inspired into entrepreneurship by feedback I’d been given about always being “organized and efficient.” Before launching A Pleasant Solution, I learned closet and space design while working for The Container Store. I took courses in Residential Organizing, Life Transitions, and Home Management through the National Association of Productivity and Organizing Professionals. I also chose to become a caregiver for my mother, who’s living with dementia. Partnering with my brother, I decluttered, downsized, and moved her to Michigan in a span of a few weeks.
For the first two years of my business, I organized in clients’ homes. However, I noticed that many of the women I worked with were carrying a layer of mental clutter too. Internal emotions like overwhelm, anxiety, guilt, and shame were showing up as exterior clutter and overcommitment. Their deeply held beliefs around what it means to be a “good” wife, mother, professional, homemaker lead them into overwork and burnout. They often kept their mental load to themselves while trying to do it all.
My experience as a parent, as a caregiver, as someone running multiple households informs my work with clients. I want them to understand that home management, organization, and sharing responsibilities within the home can be learned, and that it starts with believing that change is possible within yourself and your work-life relationship.
It has been said that our mistakes can be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?
One of the funniest mistakes I made involved a location mix up for a closet installation. A client hired me to design and install several bedroom closets. Each design, no matter the client, was stored on my business design account through The Container Store. On the morning of the scheduled installation, I received an odd call from a previous client. She was slightly confused as she had just answered the door and found the closet installation team on her doorstep. Her closets had been installed the previous month. Wrong house, wrong client. The correct client, in another part of town, was left waiting wondering where the team was. Of course, it wasn’t funny at the time and left me scrambling to untangle the mix up and understand where the error occurred. I learned that no matter how organized or detail-oriented you think you are, there’s always a chance you’ll miss something.
What are some of the most interesting or exciting projects you are working on now? How do you think that might help people?
Right now, I’m focused on showing and sharing how the invisible, mental load that we carry impacts everyone in the household. Unpaid labor — such as caring for others, scheduling, logistics, and maintaining a home — it all takes time. Noticing what needs to be done is as important as executing it. The tasks must be made visible so that they can be valued.
Women are raised to always be gauging the mood and comfort of others, anticipating what’s next on the schedule, and to drop what they’re doing to help others. This takes us away from income producing work. It drains our attention span, our energy, and impacts our overall wellness. By highlighting the mental load and how responsibilities are divided within the home, families will be in a better position to discuss the chore gap and actively re-balance the load so that everyone’s time is valued.
OK, thank you for all of that. Let’s now shift to the core focus of our interview. This will be intuitive to you but it will be helpful to spell this out directly. Can you help explain a few reasons why it is so important to believe in yourself? Can you share a story or give some examples?
Believing in yourself is the easiest, most direct step to the change you’re seeking. For example, my clients often hold the belief that they’re disorganized or poor with time. Yet, every single one of us is more organized than we think. Organization is central to how we move throughout our days, how we create income and meet our basic needs, and how we decide what’s important and what’s irrelevant. We often gloss over the many ways in which we’re already on our way towards our goal.
Start by looking for ways in your day that you already are organized, good with time, or on your way towards your new identity. Every instance, no matter how small, counts as a success. It’s up to you to validate yourself. Build a repository of these successful moments by writing them down or recording a voice note. Keep track so that you have a reference point. You’re most likely not giving yourself enough credit! If you’ve gotten out of the house on time with all your belongings most days, that counts. If you submitted a project on time, even a minute early, that counts. If you’ve noticed that the car needs to be serviced before an alert is triggered, that counts.
We often set our own expectations or measuring stick so high that the distance to our goal seems impossible. Yet, believing in yourself is a journey. It’s important because it creates the feelings necessary to move you one step forward.
What exactly does it mean to believe in yourself? Can I believe that I can be a great artist even though I’m not very talented? Can I believe I can be a gold medal Olympic even if I’m not athletic? Can you please explain what you mean?
No one can hear your thoughts. Therefore, you can believe anything you want, including that you’re organized, productive, and efficient. It all starts with a glimpse that something is possible. Believing in yourself is a process of first considering that the growth you desire is interesting, engaging, and worth exploring further. It’s often starts as a quiet voice in the background that your mind loops back to more and more frequently.
During the pandemic, I decided to teach myself how to run. I didn’t jump straight to the thought, “I’m a runner.” However, my belief grew every time I jogged for 10 seconds. I built my endurance to a minute, then several minutes. Now it’s up to a solid 45 minutes. I’d notice that my inner voice would tell me that I needed a break or to slow down, but I’d challenge my body to keep going. I put one foot in front of the other again and again. I now believe I’m a runner, even though I’ve never ran in an official race.
Your thoughts, the internal dialogue that you have with yourself, that is what creates your reality. By practicing a somewhat believable thought, it becomes more believable. It helps direct your brain to look for concrete evidence to support that thought. Once that initial thought is believable and in reach, you choose another that’s a step ahead.
Here’s another example: the words “messy” and “disorganized” simply describe what one person thinks about a space. Another may look at the space and think that it’s “tidy” or “organized.” We all have different metrics and interpretations of words, and you get to choose the words to describe how accomplished you are at any one thing. The more you practice telling yourself exactly what to believe, the more your brain will listen. Pair the belief with action, and you’re on your way.
Was there a time when you did not believe in yourself? How did this impact your choices?
Launching a business isn’t for the feint of heart. There have been many moments where I’ve questioned my path. In the beginning, I wasn’t sure how to pivot my business from in-home organizing to strictly coaching. I wasn’t sure if clients would be willing and vulnerable enough to share their grief with me, for example. When someone experiences grief and loss, they often choose to hold onto the person’s physical belongings to save a piece of that person. Yet, this is some of the most powerful work I do.
Shaky belief can slow you down by placing you in a cycle where you second-guess your choices. With grief, I wasn’t originally confident that organizing a client virtually (rather than in-person) would be possible. The key is to notice that you’re questioning your choices, to notice that your belief is wavering, and to take a moment to comfort and support yourself. Your brain isn’t always eager to embrace change or a personal challenge. The discomfort is normal and the more you expect it to occasionally pop up, the more you can see that shaky belief is part of the growth process.
At what point did you realize that in order to get to the next level, it would be necessary to build up your belief in yourself? Can you share the story with us?
Becoming a caregiver for my mom, who’s living with dementia, required a good deal of personal belief work. I was 38 years old. I had no idea what to expect. I was running a business, caring for my family, and I didn’t have peers who’d gone through this process. At first, I felt a flood of emotions. I couldn’t think rationally. I had to set aside time to feel, then set aside separate time to make conscious decisions. I started by grounding myself in the belief that I could make one decision at a time. I built my belief by focusing on my WHY, by telling myself that I didn’t need to know the entire path, and by reminding myself that how I treated myself as I tried the unknown was the most important part. I’m still actively building belief in this area.
What are your top 5 strategies that will help someone learn to believe in themselves? Please share a story or example for each.
1 . Give yourself permission to want change and dream big.
Clutter has a way of creeping onto every surface of a home, and at some point, you may feel crowded out of your own space. Or perhaps you’ve inherited clutter from another family member and those items are no longer wanted. You’re most likely overwhelmed, unsure of where to start, and feeling stuck. You want to believe that you can declutter and simplify, yet there’s a part of you that wonders if it’s even worthwhile.
Giving yourself permission to want change is a way of acknowledging where you are without judgment. Decide now that it’s going to work out and that you can complete what you’re setting out to do. This is the very first step to believing in yourself — simply entertaining the idea. Spend time thinking about the outcome you truly desire. Get as detailed about your WHY as possible. Imagine how the version who’s in full belief you thinks and feels. Consider what’s different or more expansive about this future version of you. Validate yourself. If you want it, it matters. This essential pre-work creates the possibility of growth and change before even taking action.
2 . Identify what’s currently working and build on it.
Start small. Believing in yourself happens one decision at a time. If you’re terrified of driving on the highway, get curious about the feelings you have while driving on local roads. Take a few moments to remember your first sessions behind the wheel. Remember that you once had no experience driving at all. Notice how far your belief about yourself as a driver has come. Define a plan with reasonable steps (driving on the highway when traffic is light, driving only one or two exits) and ask for support or accountability. Lean on the other moments where your emotion is steady then build from there.
When you start to tweak habits and make changes from a mindset of success, it becomes easier to believe in yourself. It becomes less about “how far” you have to go and places you squarely on the path to the desired outcome. Your mind will see new possibilities and positive risks when it feels that it’s starting from a secure, grounded space.
3 . Identify what’s standing in the way of your belief by being curious.
Learning to believe in yourself also requires you to examine the internal challenges that are currently keeping you where you are. One of the biggest justifications against believing in ourselves is that we don’t have evidence that the new pursuit will work out. Sure, there’s a chance that it won’t. However, it feels so much more exciting and enjoyable to choose to think that it will. By deciding to take the leap of belief, you’ll learn from the experience, get feedback, become more emotionally resilient, and navigate the process of growth.
Once you identify what’s standing in the way, use curiosity to poke holes in the thoughts that are holding you back. For example, if you want to become someone who leaves work at work and has hours of the day that are unavailable to colleagues, one of the obstacle thoughts may be around what colleagues will think. Yet, you truly have no idea, as most people are more focused on themselves. Actively highlight all the positive things they may think if you set a boundary on your time. It’s equally possible that you’ll be leading by example and improving workplace culture by aligning your behavior with company values.
4 . Listen to your inner wisdom.
You know yourself best. So often we’re thinking the answer is outside of us, and we value the opinions of others more than ourselves. The approval that matters most is your own. When you’re taking the leap, the way you treat yourself while taking on the challenge impacts your experience. Check in frequently with your body and notice what feels good and lights you up versus what pulls your energy down. Learning to believe in yourself may feel like a combination of discomfort and excitement.
Public speaking is a classic example. The larger the audience, the larger the required belief in yourself. Visualize yourself in front of the audience. See what bodily responses come up. Consider whether you’ll need a substantial amount of recovery time for your mind and body afterwards or whether the experience energizes you. Neither internal response is better, it’s simply data to help you navigate the leap you’re about to take. No matter the outcome, commit to treating yourself with compassion and to celebrate your efforts.
5 . Practice being the version of you that’s aligned with the new belief.
Every moment of personal growth requires practice. Repeat the new belief to yourself as frequently as possible. Think about the future version of you who embodies that belief: how you dress, how you prepare, how you show up for yourself and others. Try that version of you on internally, and then when you’re ready, try it on in public. The more you envision and practice it, the easier it becomes to step into.
I wrote a blog for two years before launching my podcast. Looking back, every time I was writing a post, I was also becoming a podcaster. I was refining my voice. I was developing my ideas and becoming a better storyteller. I was showing up for my audience in a consistent and reliable way. When the idea of hosting a podcast came up, I spent time imagining my weekly routine. For months, I practiced believing I could be successful and that the podcast would resonate with my audience. I worked internally on my belief before I took action. It set the stage for the next version of my business growth.
Conversely, how can one stop the negative stream of self-criticism that often accompanies us as we try to grow?
First, drop the expectation that self-criticism will stop. It will always whisper in your ear, no matter how wealthy, organized, or successful you become. The key is to allow the soundtrack but not agree or listen to it. Your brain is an excellent liar, and its job is to keep your life steady, routine, and safe. If certain thoughts are reoccurring, get curious about where those beliefs come from and seek support from a coach or a therapist. Counteract the automatic soundtrack with the new beliefs you’re building and re-direct your mind to what’s working in your life. Gaining the skill to believe in yourself takes awareness, compassion, and the willingness to hear the self-criticism and decide to do it anyway.
Are there any misconceptions about self-confidence and believing in oneself that you would like to dispel?
Self-confidence is a skill that you can create, build, and grow within yourself. It stems from self-trust. Self-confidence isn’t a trait that some people have and that others don’t. It’s built by unlearning past habits and untangling the thinking you’ve adopted from your family, community, and media. Self-confident people have challenged themselves by setting a goal, opening themselves up to scary emotions, and being willing to fail or be wrong. That’s the number one thing that sets them apart.
What advice would you give to someone who is struggling with imposter syndrome?
Imposter syndrome is normal, and it’s a choice. It stems from some version of the thought, “I’m not worthy” or “I don’t belong.” Yet, we’re all inherently worthy. No human must earn their worth or belonging. Imposter syndrome can be shaken off by reminding yourself of a more accessible, believable thought like, “It’s possible I’m qualified to do this work” or “It’s possible I belong in this arena.” Then spend time looking for all the reasons why that statement is absolutely true.
Ok, we are nearly done. You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.
My mission is to empower women to make the world work in their favor. This starts with helping women see how they’re at the center of everything: our homes, our families, our economy, and our communities. The default mindset is that women are the foundation or the backbone, but I truly believe we wield the most positive influence when we see ourselves at the center of it all and make powerful decisions from that position.
Second, I’d offer that every one of us is more organized than we think. “Organized,” “productive,” and “successful” are all terms that we’ve made up. You get to decide what those words mean for your life, business, and home. Once you do, you’ll feel less pressure and immediately lighter.
We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US, whom you would love to have a private breakfast or lunch with, and why? He or she might just see this, especially if we both tag them 🙂
I’d love to sit down with activist and author Tiffany Dufu. She’s used her voice to bring the causes of women and girls forward and has impacted an untold number of lives through honest storytelling, accountability circles, and philanthropy. I believe we’d connect around all things homelife and the insurmountable standards society places on women to show up flawlessly everywhere.
How can our readers further follow your work online?
I’d be more than happy to connect via my website, Instagram, Facebook, LinkedIn, or you can follow my podcast A Pleasant Solution: Embracing an Organized Life .
Thank you for these really excellent insights, and we greatly appreciate the time you spent with this. We wish you continued success.