Six words: wrong race, wrong place, wrong time

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For most college freshman, the first year at University is full of new beginnings. In America, it’s implied that every new beginning is (and should be) the same. Unfortunately, that isn’t always the case. It certainly wasn’t the case for me.

My life has certainly had its moments— I’ll admit that even my worst experiences played a role in shaping me into the person I am today.

However, the experience I’m about to describe below shaped me so greatly that I can’t wear two headphones in public out of fear that the situation could happen again. …


Don’t force yourself into these sticky situations

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I’d had enough.

It had already been 3 months. I had completed their new website in the first month and a half. I even did their copywriting. And I don’t mean just their front page — this included building and writing copy for a form so long, scrolling through it felt like a marathon.

As someone with a background in human-centered design, being tasked with this was torture. However, try as a I did, I simply couldn’t convince them otherwise. If you‘re a freelancer, failing to convince a stubborn client with bad taste is likely a situation you have dealt…


The challenges of learning to accept who I am

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I thought I had accomplished everything that was required to be “successful” enough. After all, I had lost the weight, exposed my inner demons for what they were, and learned to accept what I couldn’t control externally.

Or so I thought.

But even after 4 years of consistent self-evaluation, self-development, and self… everything, I still felt alien to the one person I was trying to “improve” upon. Myself.

I realized that my entire “self-improvement” mindset was built upon one fundamental lie that I had been telling myself the entire time. The lie that who I truly am was not acceptable…


The widely touted lifestyle has its benefits — and its social setbacks

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“When people visit you, they’re going to think you’re some kind of serial killer!”

This is what my sister-in-law told me when I mentioned I don’t own any furniture or television sets and don’t plan to own anything of the sort in the future.

It’s a choice that has gotten me a lot of flack from family members. It’s also a conscious choice I made because I realized what is truly important to me: investing my time and money into experiences instead.

You’ve probably heard of this type of lifestyle: Minimalism. It’s a pragmatic style of living brought into the…


A past of struggle can be a blessing and a curse.

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When looking back at the obstacles we overcome, there is one theme that continues to shift as we grow as human beings: our relationship with money.

It’s a complex subject, really — and as someone who grew up in poverty, I have seen money used in some of the most foolish ways imaginable. I also saw my common sense approaches to finances (saving for something I wanted) end in failure (my savings were constantly stolen from me, eroding my sense of security as a child).

Despite those setbacks, what remained unfettered were the timeless lessons I learned about money that…


Methods that transform procrastination into proactivity

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If you’re reading this, you’re the average corporate employee of the 21st century. To put it simply: you do the work of multiple people.

Welcome to 2021, where career burnout has continued to rise, even with the introduction of productivity and project management software to the workplace.

You have a lot of responsibility. You like to think of yourself as kind of a superhuman because of your ability to get so much done. And while your wide range of skills come in handy, you often feel crushed under the weight of work.

Welcome to 2021, where career burnout has continued…


And other observations that can improve your sense of self-worth as 2021 begins

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Sometimes, it is so hard to imagine that we have it all together.

As adults, it seems like we’re expected to learn and process so many new life lessons and experiences — especially in this era of constant change.

Not to mention the psychological struggles we endure: the critical development of our self-image that began in childhood comes under question once again as we are cast into adulthood.

Our sense of direction can become jaded as we begin our careers. On-the-job expectations arise and suddenly, we are faced with the powerlessness of anxiety and imposter syndrome.

While those of us…


The unspoken key to fearless creativity and joy

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There is truth to the idea that childlike curiosity is the key to opening one’s mind to learning anything new.

It’s also a well-known fact that much of our formative personality traits, as well as our most impactful memories stem from our childhood. Yet we almost never think about looking to our younger self for guidance when dealing with the complex realities of the constantly changing adult world.

This year, we have seen the COVID-19 pandemic affect every area of our lives, forcibly thrusting us into both the physical enclosures of our homes and the internal prisons of our minds.


And how it can help you design for what matters most

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Ever since I began my journey as a UX Designer, I had always designed for digital experiences.

This past week, I learned a lot about designing for conversation.

I came to realize that in our increasingly digital world, we are constantly seeing shifts and improvements in how we experience human-to-human communication. However, something we all take for granted is the art of designing for human-to-AI communication.

If you think about it, most of the technology you use depends on AI to provide you with the in-context information you need. The same is true with chatbots.

Chatbots are everywhere. Since the…


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“Unfortunately, I’m no longer in business. I apologize for the inconvenience.”

Those were the final words I spoke to my last customer. Hearing those words come out of my mouth was embarrassing and disheartening, but I knew it was time to call it quits on my personal venture after 3 months of attempting to scale my prototype startup at the time — an apartment-based garbage removal business for college students too busy and too concerned about the safety risks to walk 50–60 yards to the dumpsters during the evenings.

Before starting my first business, I had read the story of

Jon Upshaw

I write on productivity, culture, design, entrepreneurship, and life in general.

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