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8 Things My Bosses Said That Didn’t Make Sense (At First)

In the fast-paced world of digital creativity, we often encounter advice that seems counterintuitive at first glance.

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As someone who’s navigated the waters of design and technology for years, I’ve had my fair share of bosses who’ve shared wisdom that initially left me scratching my head. But as I’ve grown in my career, I’ve come to appreciate the unexpected insights hidden in their words.

The journey of a creative professional is filled with challenges, learning experiences, and moments of revelation. It’s in these moments that we often find the most valuable lessons – lessons that shape our approach to problems, refine our creative process, and ultimately make us better at what we do.

In this post, I want to share eight pieces of advice from previous bosses that didn’t make sense to me at first but eventually proved to be invaluable lessons. These insights have not only changed the way I approach my work but have also helped me strike a balance between creativity and methodology in the digital realm.

So, let’s dive into these pearls of wisdom that initially seemed more like pebbles in my shoe.

book beside laptop computer

1. “Spend more time doing nothing.”

I remember the day clearly. I was hunched over my desk, furiously clicking and typing, trying to meet a tight deadline. My boss walked by, observed for a moment, and then said something that made me question his sanity: “You need to schedule time to do absolutely nothing.”

In a field where productivity is king and every minute counts, the idea of intentionally doing nothing seemed absurd and counterproductive. We’re constantly told to optimize our time, to squeeze every ounce of productivity from our day. So, being advised to do nothing felt like career suicide.

However, as days went by and projects came and went, I began to understand the profound wisdom in this advice. I started small, allocating just 15 minutes a day to sit quietly, away from my screens. No phone, no doodling, no brainstorming – just me and my thoughts.

The results were surprising.

What I realized was that this scheduled downtime allows for a mental reset. It’s not about being lazy; it’s about giving your brain the space it needs to make unexpected connections. In our hyper-connected, always-on world, we rarely give our minds the chance to wander freely. Yet, it’s often in these moments of apparent idleness that our most creative ideas emerge.

Now, “doing nothing” is an essential part of my creative process. It’s a time for reflection, for letting ideas percolate, and for allowing my subconscious to work on problems in the background. Far from being unproductive, these moments of stillness have become some of my most productive.

2. “Make it worse before you make it better.”

During a particularly challenging design project, I found myself stuck. No matter how hard I tried, I couldn’t seem to come up with a solution that felt fresh and exciting. That’s when my boss dropped this perplexing piece of advice: “If you’re stuck, try making the design intentionally bad.”

As designers, we’re trained to strive for perfection from the start. Our instincts push us to create beautiful, functional designs from the get-go. The idea of deliberately creating something subpar felt like a step backward, a waste of time, and possibly even a risk to my professional reputation.

Skeptical but desperate, I decided to give it a try. I took my current design and started to “worsen” it. I used clashing colors, misaligned elements, and even intentionally broke some fundamental design principles. To my surprise, as I was making these “bad” choices, new ideas started to flow.

I found myself thinking, “Well if I moved this element here instead, it would look better.” Or, “What if I used this color palette instead?” Before I knew it, I was generating innovative solutions that I hadn’t considered before.

This approach, I learned, frees you from the paralysis of perfectionism. When we aim for perfection from the start, we often limit ourselves to safe, conventional choices. By allowing ourselves to explore the extremes – even the “bad” ones – we open up a world of possibilities.

Moreover, this exercise helps in understanding why certain design choices work and others don’t. It gives you a deeper appreciation for the principles of good design by allowing you to see and create contrasts.

Now, whenever I feel stuck on a project, I remember this advice. I give myself permission to explore freely, without judgment, knowing that sometimes you need to take a step back (or even a step in the wrong direction) to move forward.

low angle photography of drop lights

3. “Ignore the brief (at first).”

Early in my career, I viewed the project brief as sacrosanct. It was the guiding light, the north star that should inform every decision. So when a new boss told me to “Read the brief, then set it aside and brainstorm as if it doesn’t exist,” I was more than a little confused.

Ignoring the brief seemed like a recipe for disaster. After all, the brief contains the client’s requirements, the project goals, and all the essential information we need to deliver a successful project. Disregarding it felt not just counterintuitive, but potentially disastrous.

However, as I reluctantly tried this approach, I began to see its merit. By temporarily setting aside the constraints outlined in the brief, I found myself generating ideas that were more creative and out-of-the-box. I was no longer limited by the parameters set in the document, which often led to safe, expected solutions.

This freedom allowed me to explore concepts that I might have dismissed immediately if I were rigidly adhering to the brief. Some of these ideas, while not directly addressing the brief’s requirements, sparked innovative solutions that did meet the client’s needs in unexpected ways.

The key, I learned, was in the “at first” part of the advice. This wasn’t about ignoring the brief entirely, but about creating a space for uninhibited ideation before bringing the focus back to the project’s specific requirements.

Now, my creative process often involves an initial brainstorming session where I let my imagination run wild, unconstrained by the brief. Then, I bring these ideas back to the brief, seeing how they can be molded and adapted to meet the project’s goals. This two-step process often results in solutions that are both creative and relevant, pushing boundaries while still addressing the client’s needs.

This approach has taught me the value of balancing freedom and constraints in the creative process. It’s about knowing when to think outside the box and when to bring those thoughts back into alignment with the project’s objectives.

4. “Present your worst idea first.”

I’ll never forget the look of horror on my face when my boss suggested, “In client presentations, always start with your least favorite concept.” It seemed like professional suicide. Why would we risk undermining our credibility and wasting the client’s time by showing them something we didn’t believe in?

Despite my reservations, I decided to trust my boss and give it a try in our next client meeting. To my surprise, the results were eye-opening.

Starting with the “worst” idea set a baseline for the presentation. It gave the client a point of reference against which they could compare subsequent concepts. What’s more, it demonstrated our thought process, showing the client the journey we had taken to arrive at our preferred solutions.

But the real magic happened when we moved on to our stronger concepts. The contrast made these ideas shine even brighter. The client was more engaged, asking questions and offering insights that they might not have if we had led with our best foot forward.

Perhaps most surprisingly, there were times when elements of the “worst” idea resonated with the client in unexpected ways. Sometimes, they saw potential in aspects that we had overlooked, leading to hybrid solutions that combined the best of multiple concepts.

This approach also had an unexpected benefit for our team. Knowing that all ideas – even the ones we were less confident about – would be presented, fostered a more open and experimental brainstorming process. Team members felt more comfortable sharing “out there” ideas, knowing they might spark something interesting.

Over time, I’ve come to see this strategy as a powerful tool in client relationships. It builds trust by showing the depth of our process and invites the client into our creative journey. It turns presentations from a simple show-and-tell into a collaborative exploration of possibilities.

Now, I no longer fear showing “lesser” ideas. Instead, I see each concept as a valuable part of the creative process, each playing its role in crafting the best possible solution for our clients.

5. “Don’t solve the problem.”

When faced with a complex design challenge, I was taken aback when my boss advised, “Instead of solving the problem, find a way to eliminate it entirely.” This seemed to go against everything I had learned about design thinking and problem-solving.

Our job is to solve problems, right? That’s what we’re paid for, what we’ve trained for. Not solving them seemed like neglecting our responsibilities, like giving up before we’d even started.

But as I grappled with this advice, I began to understand its profound implications. This wasn’t about ignoring problems or leaving them unsolved. It was about thinking at a higher level, about questioning the very nature of the problems we face.

I remember working on a user interface that was becoming increasingly complex as we tried to accommodate more features. We were tying ourselves in knots trying to fit everything in while keeping the interface intuitive. Then, remembering my boss’s advice, I took a step back and asked, “Do we really need all these features? What if we could eliminate the need for some of them?”

This shift in perspective led to a breakthrough. Instead of figuring out how to cram more into the interface, we started looking at ways to simplify the user’s journey. We questioned each feature, each step in the process. In the end, we were able to eliminate several unnecessary complications, resulting in a cleaner, more intuitive interface that better served the user’s core needs.

I’ve since applied this principle to various aspects of my work. When faced with a difficult coding problem, instead of immediately diving into complex solutions, I first ask if there’s a way to restructure the system to avoid the problem altogether. When dealing with client requests, I look beyond the immediate ask to understand the underlying need, often finding simpler, more elegant solutions.

This approach encourages systems thinking. It pushes us to look at the bigger picture, to understand the interconnections between different parts of a problem. Sometimes, the most elegant solution is to reframe the situation so that the original problem no longer exists.

“Don’t solve the problem” has become a mantra that reminds me to think critically about the challenges I face. It’s about finding root causes, questioning assumptions, and sometimes, realizing that the best solution is to change the game entirely.

6. “Work on your worst skill.”

In a performance review, I was shocked when my boss said, “Dedicate significant time to improving what you’re worst at, not what you’re best at.” This advice flew in the face of popular wisdom about focusing on your strengths and delegating your weaknesses.

I had always believed in playing to my strengths. After all, isn’t that where I could add the most value? I thought focusing on weaknesses was a waste of time that could be better spent honing my expertise in areas where I already excelled.

Reluctantly, I decided to give it a try. I identified my weakest skill – at the time, it was data analysis – and committed to spending a few hours each week improving in this area. The first few weeks were frustrating. I felt like I was spinning my wheels, making little progress, and missing out on opportunities to shine in my areas of strength.

But as I persisted, something interesting began to happen. Not only did my data analysis skills improve, but I started to see connections between this newly developed skill and my existing strengths. My improved understanding of data began to inform my design decisions, leading to more user-centric solutions. My presentations became more compelling as I incorporated data-driven insights.

What I realized was that improving your weakest areas not only makes you more well-rounded but also enhances your strengths by bringing new perspectives and techniques to your expertise. It’s not about becoming a jack-of-all-trades, but about developing a more holistic skill set that allows you to approach problems from multiple angles.

Moreover, this process of struggling with a new skill and gradually improving taught me valuable lessons about learning and perseverance. It made me more empathetic to teammates who might be struggling in areas where I’m strong, and more patient with myself when facing new challenges.

Now, I regularly assess my skill set and intentionally work on areas where I’m weakest. This practice has made me a more versatile professional and a better collaborator. It’s taught me that true growth often lies just outside our comfort zone.

7. “Celebrate your failures loudly.”

I was dumbfounded when my boss announced in a team meeting, “When you fail, share it with the whole team – in detail.” In a competitive industry where we’re often judged by our successes, the idea of broadcasting my failures seemed counterintuitive and potentially career damaging.

Failures felt like something to be ashamed of, to be hidden away or quickly forgotten. Sharing them openly? That felt like professional suicide.

But as our team cautiously began to adopt this practice, I witnessed a remarkable shift in our dynamics and our work. The first time I shared a significant failure – a design that completely missed the mark with a client – I was nervous. But the response from my colleagues was eye-opening. Instead of judgment, I received empathy, support, and most importantly, insights that helped me understand where I went wrong and how to improve.

As this practice became more commonplace, I noticed several positive changes:

  1. It created a culture of learning. Each shared failure became a lesson for the entire team, allowing us all to grow from individual experiences.
  2. It encouraged innovation by reducing the fear of failure. Knowing that failures would be treated as learning opportunities rather than career setbacks made us all more willing to take calculated risks and try new approaches.
  3. It prevented others from making the same mistakes. By openly discussing what went wrong, we created a knowledge base that helped the entire team avoid similar pitfalls in the future.
  4. It built trust and fostered a more open, collaborative environment. Vulnerability bred empathy, making our team more cohesive and supportive.
  5. It led to better problem-solving. When failures were out in the open, the whole team could contribute to finding solutions, often leading to innovative approaches we might not have considered individually.

Over time, I came to see that celebrating failures wasn’t about reveling in mistakes, but about valuing the growth and learning that come from them. It was about creating an environment where it’s safe to take risks, to push boundaries, and to learn from the inevitable missteps along the way.

Now, I see failures not as something to be feared, but as essential stepping stones on the path to success. By sharing them openly, we transform them from personal setbacks into collective opportunities for growth and innovation.

8. “Design for your neighbor, not the user.”

The last piece of advice that initially baffled me came during a UX design project. My boss said, “Instead of designing for the target user, design as if your neighbor will use it.” This seemed to go against everything I had learned about user-centered design.

We’re always told to focus on the target audience, to immerse ourselves in user research, and to craft experiences tailored to specific user personas. Designing for a random neighbor seemed to ignore all these principles of user research and targeted design.

However, as I began to apply this advice, I uncovered its hidden wisdom. The neighbor, in this context, wasn’t meant to be taken literally. Instead, it was a prompt to design for universal usability.

When we design for a specific target user, we often make assumptions based on their supposed level of expertise or familiarity with similar products. But by imagining our neighbor – someone who might not fit our user profile at all – using our product, we’re forced to question these assumptions.

This approach led me to create interfaces that were more intuitive and accessible. I found myself explaining features more clearly, simplifying complex processes, and generally making design choices that improved usability for everyone, not just our target demographic.

Moreover, this mindset helped in creating more inclusive designs. By considering a broader range of potential users, we naturally began to address issues of accessibility and diversity that we might have overlooked when focusing narrowly on our target audience.

An unexpected benefit of this approach was that it often led to innovations that appealed to our core users as well. By solving problems for the ‘neighbor,’ we frequently uncovered solutions that made the experience better for everyone.

This advice taught me the value of designing for clarity and simplicity. It showed me that if your neighbor (who isn’t the target user) can understand and use your design, it’s likely truly intuitive and accessible to a broader audience, including your actual target users.

Now, when I approach a new design project, I still do my user research and create my personas. But I also take a step back and ask myself, “Would my neighbor understand this? Could they use this easily?” This extra perspective often leads to more universally appealing and successful designs.

Embracing the Counterintuitive: Your Turn to Challenge Convention

These eight pieces of advice, as strange as they initially seemed, have become valuable tools in my creative arsenal. They’ve taught me to question assumptions, think beyond conventional wisdom, and approach problems from new angles.

In the world of digital creativity, where innovation is key, sometimes the most valuable advice is the kind that makes you pause and say, “Wait, what?”

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