In Greek mythology, Sisyphus is a cunning king who cheats death twice. As punishment, Hades condemns him to eternally roll a boulder up a hill. Each time Sisyphus nears the top, the boulder rolls back to the bottom. It’s a hopeless task where Sisyphus’ efforts are constantly erased, stuck in a perpetual state of frustration and exhaustion.

The Sisyphean cycle is an easy trap to fall into. In our ambition for productivity and growth, we often set unrealistic goals for four reasons:

1. We overestimate our abilities and underestimate our needs

2. We compare ourselves to others, trying to emulate someone else’s success

3. We succumb to external influence, chasing other people’s expectations

4. We seek instant gratification, overlooking the fulfillment that comes from gradual progress

Once we realize the futility of an overreaching goal, we lose motivation, procrastinate, burn out, and give up.

The key to breaking free from these never-ending loops is straightforward: make tasks small and achievable, celebrate small wins, and create a positive feedback loop in the process.

Positive Feedback Loops

Dopamine is the neurotransmitter of pleasure and reward. It’s released not only when we achieve something but also in anticipation of a reward. The anticipation and the feeling that we’re getting closer can be more motivating than the outcome itself.

Alex Korb, author of The Upward Spiral contrasts poorly defined goals with achievable goals:

A nebulous goal might be “Spend more time with my kids,” whereas “Play board games with my kids every Sunday” is a specific one. When goals are poorly defined, it becomes difficult for the brain to determine whether you’ve actually accomplished them or are even moving toward them. Not only does that mean less dopamine, but the lack of perceived progress can be demotivating. On top of that, not believing you can achieve your goals increases feelings of hopelessness.

When we break down a long-term goal into clear, measurable steps, we use our body’s reward system to create a positive feedback loop. Completing one bite-sized task results in a sense of satisfaction and motivation to continue working towards the long-term goal. So celebrate those wins—even the tiny ones. Each one is proof you’re moving the boulder a little higher up the hill.

Bite-Size Tasks in Practice

Recently, I committed to creating a marketing landing page that displayed pricing for a Wunderite partnership: a seemingly simple project that quickly grew into something sprawling.

My first mistake was defining the task as “Marketing website content updates.” Vague. Broad. Infinite. The perfect Sisyphean setup. In reality, I should have broken the project into smaller increments:

1. Familiarize myself with our WordPress theme and tooling

2. Set up realistic-looking dummy data in our app

3. Update three product videos

4. Capture two high-quality screenshots

5. Prototype a pricing layout

6. Design a custom page header and footer

7. Record a Loom walkthrough for review

8. Incorporate team feedback

Instead, I dove straight in: overestimating my ability, comparing my design to others, feeling pressure from external expectations, and craving instant results. Each day became another round of pushing the boulder uphill.

After four days of frustration, I reframed the project:

1. I accepted the time commitment and adjusted my expectations

2. I stopped comparing my work to other designs

3. I defined a clear end goal and communicated it to stakeholders

4. I took joy in gradual progress, not perfection

Once I shifted my mindset, progress started to feel possible again.

To make sure I didn’t repeat the mistake, I created a project tracking spreadsheet in Airtable and broke future marketing tasks into half-day increments. Then I set clear boundaries with our Sales Manager:

I can commit 10–20% of my time to this project. Each week I can address one task. Please prioritize by marking them as Highest, High, Medium, or Low.

That clarity was liberating. What felt like an endless hill became a series of manageable steps: each one achievable, each one a small win.

The Power of Tiny Wins

When you’re facing a monumental project, break it down into ridiculously small and specific tasks.

I followed this same principle to write this article. My goal was to finish the draft, but on days when I couldn’t find the motivation, I’d give myself one simple target: write a single sentence. One sentence became two, then a paragraph, and eventually a complete draft.

Feeling stuck or hopeless isn’t failure. It’s a sign to simplify the goal and make progress possible again.

It takes awareness to remember that slow progress still counts. Sisyphus was doomed because his effort never accumulated. The boulder always rolled back down. But your boulder doesn’t have to. Every small task you complete, every moment of celebration, pushes it a little further uphill. And unlike Sisyphus, you get to keep what you’ve built.

That’s the quiet victory of bite-size progress: it compounds. Each small effort builds on the last until progress starts to feel inevitable. Over time, you look back and realize the mountain isn’t quite so steep anymore.

The next time you feel stuck or overwhelmed, don’t curse the hill. Just pick one small rock, move it forward, and celebrate that win. Because the difference between futility and fulfillment isn’t the size of the task, it’s whether you let yourself feel the reward along the way.

Customers buy products to do a job. By identifying what jobs customers hire your software to do, you can simplify your user experience and increase customer value, engagement, and likelihood that they will renew.

When we started Wunderite, we had a core group of early adopter insurance agents that were engaged, using the software, and giving us feedback. The pain was real and our sales team could sell, but not everyone who bought would engage. To successfully grow into our next venture capital round, we had to figure out how to replicate our early adopter success to a broader insurance agency audience. 

At the time, Wunderite was best defined as a system: a collaborative platform to manage risk data and forms. There were a lot of places to click around and there was a lot of data that could be manipulated and shared by the user. But we didn’t have a “Jobs to be Done” mentality. Agents were hiring us to quickly share and complete a form, but we hadn’t identified that yet.

Clayton M. Christensen suggests in Competing Against Luck that when people purchase a product, they’re really “hiring” the product to help complete a job. Feature-rich products are useless if they don’t actually help their users easily complete the job they’re trying to accomplish. When that happens, customers “fire” the product and look to hire an alternative to help solve the problem.

We didn’t want to get fired!

Define the problem

Early at Wunderite, it took an agent 19 clicks before they could start filling out a form–and the user had to memorize what the steps were and where to click next. If an agent had an existing profile they were working on, it would take 14 clicks. The user journey went something like this:

1. Create a risk profile.

2. Add basic account information (phone number, address, website).

3. Add property locations and buildings; automatically pull insurance data from a third party (building material, flood zone, distance to fire hydrant, etc.

4. Add vehicle schedules; automatically pull vehicle data from the NHTSA (year, make, model horsepower, etc.)

5. Add other risk data like drivers, equipment, workers comp codes, etc.

6. Add contacts and collaborators.

7. Fill out forms. Automatically answer questions using data pulled from the profile.

As our user base grew and we started talking to more agents, we realized most of them were “hiring” us to do one job:

1. Help me fill out forms faster so I can write more business.

The preliminary profile setup slowed agents down at best. At worst, they got confused and dropped off. Wunderite was at risk of being fired. Agents were hiring us to fill out forms faster and we needed to figure out how to accelerate the process.

Identify the constraints

We had two main constraints: technical debt and engineer availability. We were learning on the fly while building the first iteration of Wunderite and we accumulated some tech debt in the process. Tech debt is similar to financial debt, except instead of your payments being due in dollars, they’re due in engineer man-hours.

You can take out a “loan,” but if you don’t keep up with the payments, it becomes so burdensome that you don’t have any resources to do anything other than service the loan. At some point the loan is due.

In other words, if too much tech debt is allowed to accrue, you end up spending all your time patching the software and trying to avoid a critical meltdown, rather than building new features. Our tech debt situation presented us with some constraints:

1. A form must belong to a profile. It can’t exist standalone, meaning…

2. We need to allow agents to create a profile and add a form at the same time.

3. Our only available resource was a frontend engineer, meaning…

4. No new backend API calls.

5. Can’t edit any existing pages.

6. We can only add overlays or create interstitial pages.

In addition to tech debt, we also had limited engineer availability: everyone on the team was committed to top projects.

Design a solution

Once we defined the problem and identified the constraints (arguably the hardest part of the process), we had a good sense of what the solution should look like: Start a form in as few clicks as possible, given our constraints.

1. Start a form right from the homepage. Make it obvious.

   

2. Build a connecting page to display our forms library–no fluff or extras.

   

3. To address the “form must belong to a profile” constraint: include a step to add the form to an existing profile, or create a new one using name only.

   

4. If needed, create a new profile in the background–no additional clicks.

5. Fill out the form.

At each step of the new flow, users had a single action to complete. We kept the flow simple and sidestepped the technical debt, because there was little interaction with our existing app.

We combined the profile select and create process into a single step. Regardless if our users were starting from scratch or working with an existing profile, the number of steps were the same. With the new focused workflow, our users could start filling out forms in 5 linear steps instead of 19 disconnected steps.

Adopting the Jobs to be done Framework

The project went so well that it became a model for all future features. Three principles guided the process and focused our efforts:

1. What job is our customer hiring us to do?

2. Identify the constraints.

3. Keep it simple.

In the process, we built reusable components that are simple, effective, and scalable. Each new project we commit to can be completed faster by using existing components–building blocks to rely on. With some UX, QA support, and one full-time frontend engineer, we sidestepped months of technical debt and designed, tested, and shipped our top feature or “job to be done” in less than 30 days.

Even if you have good rapport and a public track record of excellence, your employer probably doesn’t know the extent of your work. Show them. You also probably don’t realize the extent of your work. Remind yourself of your progress.

Prior to joining Wunderite, I worked at established companies that had periodic formalized reviews. Sometimes the review process was rigid—limited at demonstrating someone’s true impact at a company. But at least it was a starting point.

While working at an early-stage startup, it can be easy to forget about rituals that are routine at established companies. People are invested in building the product, they’re working hard, and they might not think about the finer processes of Talent Management.

Impacts and assessment

A year and a half into my time at Wunderite, while reviewing my work log, it occurred to me that “no one has really seen my work log except for me.” Right then I started reflecting on my work in a file called 2021 Personal Retrospective. It was rough. I had no defined audience and there was hardly any structure: free flowing thought. But the process forced me to reflect on my work, explain my decisions, consider how I could do things differently, and outline goals for the upcoming year.

After I wrote my 2021 Personal Retrospective, I decided to share it with a few peers with four goals in mind:

1. My salary should reflect my impact.

2. I want to be recognized for my contributions.

3. Self-reflection.

4. I want feedback so I can improve.

Last month I went through the same process and named it: 2022 Personal Assessment and Impacts. My annual ritual is starting to take shape. Here’s an outline of the process:

1. Describe your goal(s) with specificity.

2. Define your audience.

3. Review your work and write it all down.

4. Describe impact and outcome.

5. Make a copy, then slash and burn (aggressively edit).

6. Write down three SMART goals.

Describe your goal

Reflection and introspection are powerful exercises for fulfillment and self-improvement. That’s reason enough to write a personal assessment. Map your progress and plan for the future. Do it on an annual basis, or more frequently. But maybe you have a specific goal in mind…

1. Campaign for a raise

2. Job promotion

3. Land a career job

4. College or graduate admissions

5. Personal reflection

Define the outcome that you want to achieve, with specificity. Expanding on the list from above…

1. What percentage or dollar amount raise? When?

2. What title? Which responsibilities are you willing to commit to?

3. Which role? Which company? In what time frame?

4. Which university? What are you interested in studying? When will you graduate?

5. What do you want to learn about yourself? Which skills do you want to improve?

Define your audience

Your audience should be determined by your goal. Are you addressing a manager, business partner, future employer, yourself, or someone else? Draft your personal assessment with your audience in mind, so that your language and voice is targeted and appropriate. Write for the reader, not the writer.

Use a work log to track how you spend time

A work log should honestly record how you spend your time day-to-day. For me, a work log is not where I prioritize, brainstorm, or reflect on my work (I have a journal for that). It just tells me what I did on a particular day. I use a spreadsheet with several columns that outline where I frequently spend time (e.g. Research, Prototype, Meetings, etc.)

If you’ve never contributed to a work log, start right now. Take an hour and retroactively review all your contributions made in the last year (or more). Refer to email, Slack/Teams/messaging, Jira/Basecamp/project planning software, task lists, and any other paper trails that will help jog your memory.

Don’t limit yourself to work that falls within your job description. Consider all areas where you have an impact. Write everything down. Now is not the time to be discerning.

Describe impact and outcome

Use a subheading to outline each project or achievement in 6 words or less. For each project, add 1-3 bullet points that describe impacts and outcome in 20 words or less. Use specific numbers to illustrate your impact. For example:

• Yes: Designed a form workflow that increased customer engagement by 50% and decreased time to completion from 1 hour to 15 minutes.

• No: Designed an end-to-end workflow for adding a form from the agent dashboard, creating a profile, filling out a form, and sharing, all within the same wizard.

You might not have access to specific numbers; use the best data available. Get creative (but be honest). In this case, quantitative data is most effective, but qualitative data can still be useful to illustrate impact.

• Do: Honestly describe your contribution and resulting impact. i.e. “I did this, here's the impact.”

• Don’t: Boast and stretch the truth. i.e. “I’m the man because I did this.”

This is also an opportunity to practice writing to your audience. Don’t assume that your audience has full context about projects you contributed to. In most cases it’s appropriate to describe your work in simple industry terms. For example, if you’re a software engineer, address your assessment as if the reader is not an engineer, but has elementary knowledge of your industry.

Depending on the scope of your work, it may be helpful to organize your projects and achievements by theme. For example, my personal assessment has these themes:

• UX Projects

• Scalability and Maintainability

• Hiring, Recruiting, and Investing

• Company Culture

• Looking Forward (more on this below)

BLUF (bottom line up front)

BLUF is a communication technique originating from the military. The premise: life-or-death decisions could be made using your information, so lead with what’s most important. Don’t bury the lead.

The stakes probably aren’t as high in your case, but you should highlight the most relevant experience that you are proud of, in descending order. As Steven Krug says: Don’t Make Me Think.

Slash and burn

“Editing” often implies a light touch. In reality, you should be prepared to rip out at least 50% of your draft, if not more. Don’t just tweak grammar and vocabulary. Be judicious with your words. Start by creating a backup copy of your personal assessment, then get heavy-handed with a thick red marker (or liberal use of the Delete key).

The first article I published on Substack started out as a Twitter thread. It was a valuable lesson in editing. Without relying on cheap abbreviations or slang, use the 240 character limit to sharpen your writing by scrutinizing each word. What’s essential to your message? What fluff doesn’t add value? Write clearly and concisely.

Plan for the future

The goal of a personal assessment is to highlight accomplishments and past work. But you should also learn from the retrospective process and apply it to the future. End your personal assessment by writing down three SMART goals (an acronym commonly attributed to George T. Doran and Peter Drucker): specific, measurable, achievable, realistic, and time bound.

Consider:

• What is exciting, fulfilling, and worth further pursuit?

• Where can I make the biggest impact?

• Where can I improve?

• What mistakes can I learn from?

Organize each goal into a subheading and add 3-5 bullet points summarizing your SMART criteria for the goal. After completing a draft of three SMART goals, edit your personal assessment end-to-end.

By the end of the exercise you should have a summary of all major accomplishments listed as subheadings with most relevant and impactful experience at the top, outcomes concisely illustrated with numbers, organized by theme, and three SMART goals for the upcoming year. Go get that raise, promotion, or job. Write a personal assessment and see how much you’ve grown.

If your personal wellbeing isn’t reason enough to enforce boundaries, because you think it might interfere with your company, job, customers, or relationships, consider the alternative: without boundaries, your peers will only ever connect with a frazzled half-focused version of you.

Learning how to set and communicate boundaries is on my shortlist for “most life-changing skill” that I’ve learned as an adult. The communication part of boundaries is critical.

I spent most of my life thinking that I was on the far end of the introversion-extroversion bell-curve. I had a rough estimation of my psychobiological needs, but because I didn’t know how to convey them, I was beholden to the idea that I was a strong introvert. I erected a handful of imposing and rigid barriers instead of setting small, reasonable, and frequent boundaries. I later found that personality assessments measuring the Big Five personality traits* placed me somewhere in the middle, even slightly extroverted.

Boundary basics

Boundaries aren’t just about social limits. I think of them as: where socialization and habit meet restraint. They are a means of setting limits to strengthen long-term wellbeing and relationships. I use them in a multitude of ways:

• Physical spaces

• Food and drink

• Calendars and time

• Devices

• Social activities

• Practically anything that encroaches on psychobiological needs

To start, I define a clear vision of the intended outcome:

1. Recognize a need. What is a habit, behavior, or interaction that is causing angst?

2. What would an idealized version of that interaction look like?

3. What steps need to happen to reach the ideal scenario?

4. If the ideal scenario is out-of-reach, what is a smaller iteration that can be achieved?

Between the rational and subconscious

It can be helpful to first practice setting boundaries at a personal level, without the added complexity of relationships. This is between your rational and subconscious selves. Here’s how I use the checklist above to set a boundary with my phone:

1. I’m spending too much time on my phone. Social media claims to enhance connections, but I feel disconnected from reality. Friendships on social media feel fake, while in-person they feel hollow.

2. I find utility in having a smartphone. It’s useful for navigating with maps, listening to music (brings me a lot of joy), learning via podcasts, taking photos (photography is a hobby), and keeping in touch with people (preferably via phone calls as opposed to text or social media).

3. Ideally, I would only use my phone for features listed above, not much else, but…

4. Phone use is pervasive and enticing. I’m not going to change everything at once. I’ll start small. No phone in the morning until after I’ve gone through my normal morning routine (about 2 hours after I wake up).

I set my boundary, but to ensure success, I made a few lifestyle changes (make it easier on yourself. There’s no need to unnecessarily go through life on “Hard” difficulty):

• My phone stays on silent and charges away from my bed. If I want to use it, I have to physically get out of bed. No more scrolling while in bed.

• I bought a digital alarm clock with a night light—no using the excuse that I need my phone next to me as an alarm or to check what time it is.

• If I have to check the weather in the morning, I do it the old fashioned way by poking my head out a window or door, or I can also look at my thermostat (many contemporary digital thermostats give you weather updates).

Setting social boundaries

Successfully setting boundaries with yourself can be fulfilling, but it’s like practice for the big leagues: setting social boundaries with others. There’s a common fear that this will create friction between you and others, signaling:

• You're unfriendly.

• You don’t care.

• You aren't committed.

In reality, if you can communicate boundaries effectively, people will generally have more respect for you. They recognize that you prioritize personal wellbeing and are confident enough to define and communicate your limits.

Also, people thrive in clarity. When you’re specific and considerate explaining your limits, relationships will flourish as others know what the rules of engagement are.

Practical tips for boundaries

Enforcing boundaries with others can be uncomfortable, but there are some practical steps you can take to make the process smoother.

Communication

• Be honest. If you make a habit of lying about why you're unavailable, people will lose trust in you and you'll miss out on an opportunity to have honest conversations about what your limits are. If you aren’t comfortable sharing details, say something like “Sorry, I’m unavailable then,” or “I can’t commit to that.”

• Provide alternatives. Relationships require negotiation. Providing alternatives prevents alienation and lets people know you’re committed. For example: “Happy hour doesn’t work for me. What about lunch instead?” Or: “I can’t commit to a one-hour meeting then. What about 30 minutes on Tuesday at 10am instead?”

• Be firm but polite. Most people are considerate and respectful, but if someone is trying to take advantage of your boundary, be firm but polite. Provide alternatives and stand your ground.

Automate and separate

• Use notification settings. Turn off push notifications on most (or all) apps, especially Slack channels and group chats. Set yourself away or pause notifications when you need to focus. Use app settings to define working hours and automatically turn off notifications

• Block time on your calendar. Create recurring calendar events for 1-4 hours at a time, during hours of the day when you work most effectively. I use Google Calendar’s “Focus time” to block off “Design Focus” every Monday-Friday, 7am-9am.

• Create email filters. Use a combination of sender email address, subject, or keywords to create an email filter. You’ll still receive useful notifications, but they won’t distract you by going to your primary inbox. For example, I find utility in receiving Jira Software notifications, but they shouldn’t take priority over regular email. They get relegated to a Jira inbox that I can check at my leisure.

• Create physical boundaries to reinforce psychological boundaries. This is especially useful for devices, food, and drink. Create a literal physical boundary by placing items out of sight and reach. If you’re watching a movie, put your phone and snacks in a separate room so that you’re not tempted to indulge.

Reaching a breaking point

Working at a startup naturally requires a generalist mindset. I’m technically the Manager of UX, but I get involved with everything: QA (quality assurance), product requirements, release notes, customer success, support, marketing, code contribution, code reviews… I’ve even setup a handful of sales and investor calls.

I fell into a habit of “getting caught up” with email, Slack, and Github at the start of every morning. It’s a bit of a joke, because it’s not possible to truly get “caught up.” I placed the needs of others above my own, which lead me into an anxious state of chaos, playing a never-ending losing match of ping-pong. I reached a breaking point this past January.

While coordinating several major feature releases, I broke down and lost it. I took some personal time off in the middle of the week and spent the day at my favorite beach. I read my Kindle while soaking in the sun, I went for a swim, and I treated myself to a waffle cone (I love ice cream). It was incredible; it was exactly the reprieve I needed.

Yet my day at the beach was temporary. Having a generous PTO policy is wonderful and I’m thankful that I could sporadically take a day off in the middle of the week. But when I went back to the office the next day, I resolved to change my boundaries so that I wouldn’t have to take a random day off because I was squandering the most productive hours of my day, and boiling over with stress in the process.

Imposing focus time changed my life

I used Google Calendar to set “Focus time,” every Monday-Friday 7am-9am. Truthfully it didn’t affect much in the way of scheduling. 7am-9am is a pretty quiet time of the day anyway (which is why I love mornings). But I also decided that during that time I wouldn’t even open any other applications except for Figma (design/prototyping software).

For at least two hours every morning, I completely commit to the part of my job that brings me the most joy: designing. I frequently lose myself in the flow state, zoom right past 9am, and keep designing late into the morning.

I’m still able to handle my other obligations and by starting each morning in a blissful state of focus, I’m more effective collaborating with others when the time calls for it. Creating a creative bubble energizes and reveals new connections that otherwise don’t sprout when I allow others to have unfettered access to my attention.

With the extra inspiration, I even took on a few more initiatives by regularly contributing to the company knowledge base and blog.

Working hours

Aside from “focus time,” I have a few other work boundaries that I stick to. Most importantly, I define my working hours: Monday-Friday, 7am-5pm. One caveat: some of my best ideas develop on evening walks, so I’m allowed to bring some “work” home with me…

Work that I’m allowed to bring home

• Creative ideas.

• Ideas for conflict resolution; an opportunity to apologize, own a mistake, or improve a relationship.

Work that I’m not allowed to bring home

• Slack and email.

• Tasks and projects.

• Stress, ruminating, “should, woulda, coulda.”

If I ever find myself encroaching on working hours, I tell myself: “The work day is over. Set this down for now and you can come back to it tomorrow.”

Start small and iterate

Negotiating power will vary. If you have a family, you might need to make more concessions than if you’re a bachelor or bachelorette. Maybe your work environment doesn’t afford the kind of leeway you prefer. Don’t abandon your efforts. Think smaller. Start by setting manageable boundaries, then iterate. Maybe you can’t block off two hours every day for focus time. What about an hour? 30 minutes? Or try enforcing a strict lunch period: 30-60 minutes of complete personal time. As Dr. Alex Korb notes in The Upward Spiral:

The important thing here is not actual control, but perceived control. Making decisions may not increase your actual control over a situation, but it will likely increase your perceived control. And when you increase your perceived control, you increase your confidence, mood, and future decision-making capabilities.

Try making small, incremental, and practical changes today by reviewing sources of angst, defining your limits, and creating a vision for an alternative ideal. Then communicate to your peers verbally and with automated notification settings. Through consistent repetition you’ll hopefully find a greater sense of focus and less frazzled chaos.

I’m barely skimming the surface. Entire books have been written on this topic. Anecdotally, I emphasized digital boundaries the most. That’s because they tend to be the greatest source of discomfort for me.

*I’m aware of critiques of personality assessments, including ones that measure the Big Five. They can still be useful tools for bringing awareness to personality tendencies, recognizing that people aren’t static, and realizing that people are capable of positive life changes.

Effective teams (and individuals) name the behaviors they want to repeat and define the principles they want to adhere to. It’s a bit of a self-fulfilling prophecy: name and define, live them, repeat them. If you don’t define the vision, then it’s impossible to truly know what you’re building towards.

Jon Yablonski, author of Laws of UX (book) and the companion website, knows this. Laws of UX is “a collection of best practices that designers can consider when building user interfaces.” In Chapter 12 of the book he details a workshop for defining a company’s Design Principles.

Design Principles are useful because…

1. They are guidelines that represent the priorities and goals of a team and serve as a foundation for reasoning and decision making.

2. Allow the company to efficiently scale by decentralizing the design decision making process.

3. Help to frame how a team approaches problems and what it values.

4. Prevent bottlenecks from occurring by creating a shared understanding of what a successful design solution looks like.

5. Design decisions become quicker and more consistent.

The need to define Wunderite’s Design Principles became apparent as our team grew. It was relatively easy to maintain consistency with a small team. But as the team grew, it became increasingly challenging to maintain a unified product experience without getting bottlenecked by a few stakeholders.

To address this, we collectively workshopped our Design Principles

1. First we defined the team that would author the Principles. Who would have a stake in our product vision? We made the exercise mandatory for our entire Product-Engineering team and optional (but encouraged) for the rest of the company. Founders Peter and Joe also participated. In preparation, we circulated resources including Laws of UX (specifically Chapter 12: Applying Psychological Principles in Design) and an internal summary slide deck.

2. Second, we defined the success criteria for an effective design principle:

   1. Principle should be direct, clear, and actionable, not bland and obvious (e.g. "design should be intuitive" is too broad)

   2. Principle should solve a real question

   3. Principle should be opinionated (e.g. what elements and features are we choosing to prioritize?)

   4. Principle should be memorable

3. Then we diverged and gave everyone the opportunity to individually brainstorm what they thought would be important as a Design Principle. Given the distributed and remote nature of our team, operating across a lot of time zones, we decided to address this like a homework assignment. We created a Google Form for participants to submit their Principles.

4. Next, we converged in a meeting and reviewed the submissions as a team and voted on which ones we thought best aligned with our company goals and success criteria.

5. Once we had a final list of Principle candidates, we consolidated similar themes and refined the language of each Principle, to clearly articulate the expected outcome.
   Note: Since running this workshop almost two years ago, we’ve become more effective at working and collaborating as a remote team. We also have a smaller span of time zones to work across, so the logistics are less challenging. If I were to re-run this exercise today, I would consider the following:

   1. Spend more time workshopping the principles together, rather than having “homework” to submit via Google Forms.

   2. Use breakout rooms to workshop ideas in small randomized groups. (But eventually gather everyone in one group, bring it all together, and finalize the Principles).

   3. Use collaborative tools like Miro to help workshop ideas.

6. Once we were happy with the Design Principles, we associated them with psychological principles detailed in Laws of UX.

7. Finally, we documented the Design Principles in Confluence and updated our new employee onboarding checklist. The goal is to circulate and advocate. See “Room for improvement” below for some reflection on this.

Wunderite’s Design Principles

Without further ado, here’s what the team came up with, roughly ordered in terms of importance…

Use simple language

According to Tesler’s Law, any system has a certain amount of complexity that cannot be reduced. However, we should ensure as much of the burden is lifted from users by dealing with inherent complexity during design and development, especially when considering language.

To achieve this goal, we must:

• Optimize for the reader, not the writer.

• Make actions targeted and specific.

• Avoid industry jargon.

• CC Product and design managers (language is a critical aspect of the product; don’t be afraid to ask for assistance when unsure).

Clarity over abundance of choice

According to Hick’s Law, we know that the time it takes to make a decision increases with the number and complexity of choices available.

To achieve this goal, we must:

• Limit choices to no more than 3 items at a time.

• Highlight recommended options.

• Provide brief explanations when useful that are clear and no more than 80 characters.

• Use concise multi-step forms in place of long and overwhelming ones.

Be consistent

According to Jakob’s Law, users prefer your site to work the same way as all the other sites they already know. This also applies to different pages and features within Wunderite. By leveraging existing mental models, we can create superior user experiences in which the users can focus on their tasks rather than on learning new models.

To achieve this goal, we must:

• Use existing pages, components, and styles as a model for building new features.

• When necessary, use data to inform if an existing design pattern is not working effectively and iterate on it if necessary.

• Be consistent with change: if you make a change in one location, consider if a global change is appropriate depending on impact and effort.

• When making changes, minimize discord by empowering users to continue using a familiar version for a limited time.

Familiarity over novelty

According to Jakob's law, we know that users spend most of their time on other sites, and they prefer your site to work the same way as all the other sites they already know.

To achieve this goal, we must:

• Use common design patterns to reinforce familiarity with the interface.

• Avoid distracting the user with a flashy UI or quirky animations.

Give the user control

According to Postel’s Law, we know that we should be liberal in what we accept from others.

To achieve this goal, we must:

• Avoid making assumptions for the user; allow them to dictate the actions they want to take.

• Be empathetic to, flexible about, and tolerant of any of the various actions the user could take or any input they might provide.

• Anticipate virtually anything in terms of input, access, and capability while providing a reliable and accessible interface.

• Accept variable input from users and translate it to meet our requirements.

Give users feedback

According to the Peak-End Rule, we know that people judge an experience largely based on how they felt at its peak and at its end, rather than on the total sum or average of every moment of the experience.

To achieve this goal, we must:

• Identify key moments when the product is most helpful or valuable and…

• Use tasteful animations, highlighting, progress indicators, notifications, or modals as visual cues acknowledging users' actions.

• Delight the user by making feedback informative and useful.

• Experiment with comic relief or entertainment to put the user at ease (e.g. confetti when they have successfully completed a form).

• Don’t go overboard; use restraint when placing emphasis on visual elements to ensure they don’t become abrasive or cause discomfort for users with motion sensitivity.

  

Have a clear hierarchy

According to the von Restorff Effect, when multiple similar objects are present, the one that differs from the rest is most likely to be remembered.

To achieve this goal, we must:

• Make important information or key actions visually distinctive.

• Carefully consider the effect that size, color, font, proximity, alignment, and negative space have on hierarchy.

Cluster related objects

According to Miller’s Law, we know that the average person can only keep 7 (± 2) items in their working memory.

To achieve this goal, we must:

• Organize content into smaller chunks to help users process, understand, and memorize easily.

• When grouping objects, consider which actions are unrelated and drop them from the group.

Design with accessibility in mind

According to Fitts' Law, we know that the time to acquire a target is a function of the distance to and size of the target.

To achieve this goal, we must:

• Consider those with color vision or low vision deficiency by using appropriate color contrast and font sizing.

• Use a mobile-first design approach.

• Make touch targets large, with ample spacing, and placed in areas of an interface that allow them to be easily acquired.

• Use industry resources for accessibility standards:

  • USWDS: The United States Web Design System

  • WAVE Chrome, Firefox, and Edge Extensions

Confirm before you commit

According to Postel’s Law, we know that we should be conservative in what we do, but be liberal in what we accept from others.

To achieve this goal, we must:

• Give users the option to cancel or undo an action.

• For default settings, always choose the least destructive action a user can take.

Brief reflection

In preparation for publishing this article, I copied the Wunderite Design Principles that our Product-Engineering team workshopped nearly two years ago. That accounted for about 75% of the article. I added a few screenshots and GIFs to illustrate the principles, included context about how we ran the workshop, and reflected on where we could improve. In the process, I was struck by two things:

1. Examples that best illustrate our design principles are seemingly innocuous: modals, alerts, notifications, inputs, and language decisions. Interactions that are sometimes overlooked because they’re not “sexy” or not considered central to the app design. But these small and frequent interactions highlight how clear, simple, and accessible messaging are core to User Experience.
   
   Early at Wunderite, we struggled with engagement; we had many powerful features that were loosely connected. Instead of trying to solve the problem by building new features, we addressed the issue by making simple changes through language, modals, and menu actions, making features more connected and accessible.
   
   I contend that when trying to improve user experience, one of the most efficient and effective changes to make is updating language to be clearer (which is why “Use simple language” is our first design principle).

2. I was really proud of how well we stuck to our Design Principles! Our app design has changed significantly over the years, but it was still quite easy to find illustrative examples.

Room for improvement

At Wunderite, we do a great job of documenting company best practices, but we have room for improvement when it comes to circulating and advocating. Often it seems like the hard work we put into documentation gets lost when a piece of writing is relegated to a Confluence page. It can be challenging as a remote-first company, where we don’t have physical spaces to post reminders of our principles and best practices, nor do we have the same kind of opportunities for impromptu in-person encounters and collaboration. If you work at a remote-first company, how do you handle those challenges?

Things we already do

1. Write it down; document best practices.

2. Include documentation and best practices in onboarding (we have this down).

3. Use online tools for collaboration (we’re pretty good at this, but I think we could make more use of real-time tools like Miro and FigJam).

4. Reference principles and best practices in product requirements (we’re adequate at this).

5. Reiterate in meetings and discussions, like 1:1’s, scrum, grooming, and retrospectives (we could do this more).

Things we’re working on

1. Repeat and advocate. Build our principles into the stories we tell internally, with customers, with prospects, and with the public.

2. Make meetings less rigid and routine and more like collaborative workshops.

3. Be more transparent: share our process and learnings with the public (like this blog post).

4. Collaborate more frequently across departments.

Wunderite is building intuitive next generation software for independent insurance agents and their customers. If you’re curious to learn more, check us out at www.wunderite.com.

My name is Philip MacDonald and this is me daring greatly. About every other week, I plan to write about user experience design, personal growth, professional growth, and experience working at a startup. If you like this article or are curious to hear more, I’d love it if you subscribed! And if you’re feeling extra generous, tell some friends.

In 2020 I joined my brother Peter and his business partner Joe, to help build Wunderite, an insurance automation platform. I brought with me six years of Product and Design experience that I learned from previous work at established software companies. It has been stressful, exciting, and the adventure of a lifetime.

Before transitioning to Wunderite, I felt like my career had plateaued and that I wasn’t being challenged at work. Likewise, I was discontent in my personal life, stuck in a loop; the same dull movie I’d seen a thousand times over.

We had an ultra-lean team in the early days of Wunderite. I was the first full-time salaried US employee. We also had two overseas engineering contractors and one part-time QA engineer who we couldn’t afford to bring on full-time. In order to handle the stress and demands of working with a lean team, I became very serious about putting my personal life in order, resulting in an upward spiral of personal and professional growth.

It’s a special opportunity that I feel blessed to participate in, especially alongside my brother Peter. Working with family can be challenging, but it affords me a consistent voice of encouragement who is also unafraid to tell it like it is. Peter has been suggesting that the cultural best practices that I advocate are worth sharing publicly, urging me to publish my ideas on Twitter, in a newsletter, or somewhere similar. Which is where Substack comes in…

Radical transparency

There’s a concept in the software industry (and elsewhere) popularized by Ray Dalio called “radical transparency,” where people and organizations openly share ideas that may have traditionally been considered trade secrets. Financial goals, internal processes, design principles, codebases, knowledgebases, and release notes are made public, signaling:

• I'm confident in my abilities.

• I'm not afraid to make mistakes and own them.

• I'm proud of my work.

• This is a collaborative effort and we can collectively do better by being open.

Think of it as the equivalent of shedding your sweatpants and loungewear, putting on a pair of pants, and making yourself a presentable but fallible participant in the world. Radical transparency can be scary and it doesn’t guarantee financial success. But at a professional and personal level, it comes with a few benefits:

• Transparency forces you to solidify, define, and articulate your vision.

• Transparency is a great way to make deep connections; let people know “I’m not performing, this is my authentic self.”

• For companies, transparency can be a boon for meeting great collaborators, recruiting star employees, and selling to people who can truly benefit from your product.

• Transparency is a creative brainstorming exercise; the process of articulating your vision helps uncover new ideas and connections.

• Transparency is a great way to market test your ideas. You shouldn’t be beholden to public opinion, but disclosing your fundamentals can serve as a test of whether people gravitate to your message or if your idea stinks.

Why here, why now?

It’s a strange time. Many people are living in their own virtual reality. It’s easy to make snap judgements about people when their lives seem so public. In reality, we only get the soundbite version of a person’s story when we hear about it through social media or the news. A lot of people are hurting or withholding a part of themselves that they haven’t sorted out yet. Even talking to someone face-to-face barely scratches at the depth of a person’s experience.

That detachment between perception and reality motivates me to tell my own story. Own the narrative. Don’t sit back and let someone else write my life’s story. I want people to know me for me. Not someone else’s interpretation of me.

Historically I’ve been private and soft spoken; hesitant to open up to people I felt hadn't earned my trust. A side effect was being frustrated and angry that people didn’t understand me. In reality, I don’t think I quite understood myself. How could I ask others to understand me if I didn’t understand myself? Why would someone trust me if I’m reluctant to extend the same gratitude?

Trust is a two-way street. I suppose I’m trying to make the first move through radical transparency. Stories are powerful and if you can tell a good story, it can be the motivating factor to drive connection and inspire people to action.

Daring greatly

I considered a handful of places to house my ideas. Historically I would have opted for total control and spent days engineering and configuring my own blog on my own server. Ultimately the allure of using a service where I could own my mailing list and focus on writing led me to Substack. Ironically, I spent a lot of time agonizing over settings in Substack. One area that had me stumped was a name. After a bit of thought I landed on “Daring Greatly.” It’s a reference to President Theodore Roosevelt’s famous A Citizenship in the Republic speech (Brené Brown also quotes it in her 2012 book Daring Greatly), which he delivered in Paris, France on April 23, 1910. An excerpt reads:

Let the man of learning, the man of lettered leisure, beware of that queer and cheap temptation to pose to himself and to others as the cynic, as the man who has outgrown emotions and beliefs, the man to whom good and evil are as one. The poorest way to face life is to face it with a sneer. There are many men who feel a kind of twisted pride in cynicism; there are many who confine themselves to criticism of the way others do what they themselves dare not even attempt. There is no more unhealthy being, no man less worthy of respect, than he who either really holds, or feigns to hold, an attitude of sneering disbelief toward all that is great and lofty, whether in achievement or in that noble effort which, even if it fails, comes second to achievement. A cynical habit of thought and speech, a readiness to criticise work which the critic himself never tries to perform, an intellectual aloofness which will not accept contact with life's realities—all these are marks, not, as the possessor would fain think, of superiority, but of weakness. They mark the men unfit to bear their part manfully in the stern strife of living, who seek, in the affectation of contempt for the achievements of others, to hide from others and from themselves their own weakness. The role is easy; there is none easier, save only the role of the man who sneers alike at both criticism and performance.

It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better.

The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, and comes short again and again,

because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows the great enthusiasms, the great devotions; who spends himself in a worthy cause;

who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who know neither victory nor defeat.

There’s no shortage of critics in the world. In my case, I’m my own worst critic. When my internal critic gets mouthy and tells me that I’m no good, I’m defined by my mistakes, and I should keep quiet because people don’t want to hear from me, I remind him: “I’m the one in the arena. I’m out here doing the work, not you. So take a walk.” (My internal critic was raging leading up to publishing my first email newsletter).

For further reading, check out the first article I published on Substack (originally posted as a Twitter thread @philipmacd):

Daring Greatly

Learning how to dance taught me these 17 lessons...

Last year, feeling unfulfilled and disconnected, I went on the hunt for new social opportunities. Especially ones where I could meet new people, learn a skill, and commune in a setting that didn't revolve around drinking. Here's what I learned after picking up swing at my local dancehall…

Read more

3 years ago · Philip MacDonald

Last year, feeling unfulfilled and disconnected, I went on the hunt for new social opportunities. Especially ones where I could meet new people, learn a skill, and commune in a setting that didn't revolve around drinking. Here's what I learned after picking up swing at my local dancehall...

1) Receive help from others

The first time I showed up for swing dancing, I got half way through the lesson and bolted for the doors out of embarrassment. But the doorman wouldn't let me leave. He stuck two regulars on me who helped me stumble my way through a few dances.

2) Encourage others

One of the most fulfilling moments of my dancing was being paired with a beginner and realizing that I knew enough to share some help and encouragement. I saw a reflection of my earlier self and remembered all the encouragement I received along the way.

3) Confront your fears

The first three months of taking lessons and going dancing, I was terrified and would look for excuses to bail. But I persevered. Expose yourself to fears gradually and in manageable doses. Resist the urge to run. Understand and learn from fears.

4) There are no shortcuts

Want to get good at something? Practice, put in the time, get repetitions, and be consistent. There's no easy way around it. Taking the long road makes it that much more fulfilling once you master something.

5) Smile and introduce yourself

Exchanging names is the first step towards building a connection. And if you're socially anxious, it's the most basic thing you can do to ease the tension.

6) Community is a biological necessity

Treat socialization the same way you would exercise. Make it part of your regimen. Get the in-person face time. Don't let your social muscles atrophy; keep working them out.

7) Progress is not linear

You're going to fail. Sometimes you're on your game. Other days it feels like you're missing a beat. But if you show up and stick with it, things trend up.

8) We're equal in hope and desire, not skill and ambition

Some people are born with natural gifts. Others are dealt a raw hand. Some have spent decades of hard work to become who they are. There's no utility in coveting what you don't have. The most effective thing you can do is create a vision of who you want to be and work towards it.

9) Experiment and try something new

If you only stick to what you know, you'll never grow. Try a new move and see what happens. And if you mess up...

10) Laugh off your mistakes and learn from them

You can't always expect to nail it on the first try. Pick yourself up, see where you went wrong, and try again.

11) Learn from elders

In our hubris it seems like we declared that new is better, old is irrelevant, we reached the pinnacle of understanding, and technology is the solution to everything. But the problems and desires of today are the same as yesterday and tomorrow: human and timeless.

12) Be humble

What do a blind octogenarian and I have in common? We both want to laugh with our friends, make new connections, feel like we belong, and let loose dancing on Wednesday nights. Have fun and embrace the beginner mindset.

13) Everything is connected

Learn one type of dance and the next one is easier to pick up. Skills don't live in a vacuum; they are applicable across domains.

14) Be vulnerable

Don't try to cover up your weaknesses. Let people know that you are still learning, but that you are committed.

15) Get back on beat when you fall out of sync

Sometimes we get tripped up. That's no reason to stop what you're doing and apologize. Shrug it off and get back on beat, even if it means taking a second to get your bearings.

16) Default to sobriety

I'm not a teetotaler. I like to get loose from time to time. But if intoxication is typically the centerpiece in social situations, try flipping the paradigm on its head: default to sobriety and make inebriation an occasional treat, not the standard rule.

17) Be adaptable

Sometimes the music or dance partner isn't what you expected. Don't let it trip you up; go with the flow.

I originally shared this Feb 21, 2023 as a Twitter thread, but decided to reshare as an article. Check me out on Twitter @philipmacd to learn more about my professional journey as a UX designer in the insurtech industry, building Wunderite.