Logo Design for Impact

The Making of a Logo

While I’ve been known to pick up and start a lot of new projects, only a rare handful are for public consumption and reach maturity. These select ideas, the ones I’ve spent so much time and resources bringing to market, need a unique identity. Logos are big part of that identity and they serve so many crucial purposes.

For me personally, logos are a manifestation of what I’m building, why I’m building it, and the promise of future possibilities. With the help of a logo, the branding starts to work its magic on the rest of the team and myself. Every time I see that icon atop my email or on the header while developing web content, I get an extra boost to keep going.

More importantly, I see logos as the crucial anchor to a nascent brand. It sends signals to potential investors, customers, and the press. I want my logo’s first impression to convey brand feelings, such as:

  • Professional vs. playful
  • New and agile vs. conservative and predictable
  • Trustworthy vs. misleading
  • Commodity vs. unique

This is powerful stuff and I wanted to get it right.

Logos from Previous Projects

I’ve been down this road a few times with some of my other projects. The impression I hope to make really does vary based on the product itself and the audience I’m hoping to pull in. Consider these examples that fill the whole spectrum:

email-format.com is a web site that helps visitors find the email address formats used at large companies.The project was low budget from the get go, both in terms of building the product and for conveying such with site visitors.

Since the web site started as nothing more than a several hour quick hack, the icon itself is equally low-effort. The logo is an icon of an envelope that I purchased off a clip-art site.

Since most site visitors come organically looking for “free” data, keeping a consistent and unified brand keeps the overall visitor expectation consistent with the look.

Flip-a-toy was a marketplace for used children’s toys. Visitors could easily sell and discover toys to buy based on age, gender, and location.To successfully reach the target parent persona, my goal was to simultaneously convey trust and playfulness.

Use of both the monkey in the icon and the font in the wordmark both served to show this was oriented towards young children.

At the same time, a logo that was clearly professionally produced added a level of credibility to build the needed trust factor.

Appointment.one is a tool for professionals to remove all the friction from scheduling meetings by eliminating phone- and email-tag.My target persona is a professional who is always on the lookout for new tools to improve their productivity. To meet that goal, I wanted to convey both an instant connection to the product (e.g. scheduling) and to hint that this isn’t a conservative and hard to use technology.

Both the icon and the wordmark in this logo use current high-style design concepts to lend an air of fresh design.

The icon highlights concepts typical of appointments, meetings, and scheduling.


I began the process by listing the attributes associated with a typical customer. In the case of Calenzen, this persona included:

  • Calendar driven professional
  • Recognizes inefficiencies throughout their day and works to remediate those in order to make their day easier
  • Participates in multiple dial-in meetings, ideally using a number of conference providers

I’ve identified a typical customer and now begins the second step: what visuals or iconography appeal to them? More than just connecting to them, I want customers to self-select through their connections with the imagery and their own emotions. For Calenzen this meant:

  • Calendar, appointment, datebook
  • Telephone, mobile phone, dial-pad
  • Sense of calm, playfulness, clarity

Finally, I make sure to call out any specific use cases that the logo must support. I do this early in the process to avoid the risk of following a path that prevents this.

  • Square. While the logo gets star treatment on sites I control, that’s not the case when it’s used elsewhere. Consider a Twitter profile for example. It crops the logo to a 1:1 square ratio. A logo that can’t work in a square must either be cropped (bad) or require so much padding space that it is difficult to see details and recognize the logo.
  • No Words. This is an alternate scenario, also often used where a square is required. By dropping the wordmark we have even more pixels available to highlight our message. Consider a favicon for example, which in a very small space can scarcely convey an icon, let alone any readable text.
  • Single color. Though the logo rarely needs to be used with a single color, if you don’t account for this in the beginning, adding in support after the fact is clumsy. This was an issue with Appointment.one when overlaying the logo on top of an image or patterned background. The logo only fit with the rest of the design when all color was stripped from it.
The Appointment.one single color logo blends seamless with any darker background type, even this hero image on the site.

This whole process is one of the most challenging parts of logo design. For me, this is always an iterative. Importantly, only some of these visuals are actually recognizable outside of a larger context. That’s why so many of my initial designs and suggestions ultimately need to be scrapped – they can’t convey the message I’m working towards.

Testing the Waters with an Upwork Freelancer

While I feel entirely comfortable with the ideation process to this point, I fully own up to an inability to actually implement any logo or other graphic design.

In the past I’ve used design services through freelance sites like Upwork. They provide the tools that make it easy to find any number of individual freelancers with varying experience, quality, and cost. That said, my last attempt was a number of years ago and ultimately produced a poor result.

As part of another project, which was an e-commerce site, rather than using a small developer on Upwork I ended up connecting with a larger design firm. They sent along a questionnaire with dozens of example logos. The firm used this data collector to get a sense of what I wanted and it was definitely thorough.

Example logo design data collector used with the Flip-a-toy / Play-Swap project.

As complete as this questionnaire was though, it wasn’t a dialog. Instead, it was the start of a relatively static effort that didn’t move too far from my initial vision – no matter how misguided that may have been!

Design via Crowdsourcing with 99designs

Given the lesson learned years ago, there was no doubt that I’d instead work with crowdsourced designers rather than sticking with a single designer and anchoring too tightly on the initial vision.

I’ve used 99designs on at least half a dozen occasions and have almost universally been ecstatic with the process itself and the end results. 99designs is a marketplace where any number of freelancers submit design ideas for you. The site supports a broad range of design categories, but I’ve found most designers participate in efforts where they can get something out there with very little effort and then follow up with refined designs if they have something that catches my eye. This means that while logos have tons of participants, a landing page design may have only a few submissions, each of which may very well be so far from a usable entry that there’s just no way to successfully turn them around.

99designs began with a short data collector to gauge my brand and style specifications. This is visible to all designers who participate in the contest in an effort to start all new designs off from the same foundation.

99designs data collector screen 1 of 3, free-text description of what I’m looking for.
99designs data collector 2 of 3, gauging my interpretation of the basic visual style rules to follow as part of the design.
99designs data collector 3 of 3, pulling out specific images that meet my specified style.

Implementation Details

The first designs rolled in just minutes after the contest started. As a rule they were boring and blah. In all likelihood, they were repurposed with only a quick change to customize the name and had no specific alignment to the design requirements stated in the brief.

A selection of the first designs, all of which were very generic.

I understand that working on spec is challenging and payout is infrequent at best. That said, I don’t understand why these designers participated in the contest at all. Have they adopted a purely generic design and succeeded in previous contests? If not, then they have guaranteed there won’t be any payout for even the small amount of time they’ve invested.

By the next day, a second wave of designs began to flood into the project. These were largely from illustrators who read through the brief and had a specific idea they felt actually aligned to what I’d stated. Among these, I started to develop my first strong element preferences.

The first element preference was exclusionary. This wave took the time to create some custom icon illustrations. While I commend the designers for taking the initiative, the elements just didn’t fit with the brand image I was building.

The second one came when one of the designers began to play with the font color and weight as part of the design. Keeping Calenzen as a single word but still highlighting the two components felt important.

The third element was an icon that really seemed to hit a sweet spot. Turning a calendar into an animal seemed a crafty way to add just the right amount of levity to something that would otherwise be quite predictable.

With these new element preferences in hand, I sent a message to all designers participating in the contest to re-align them.

Noted three requests for change:

  • Preference for using differing font-weight or colors to separate the “calen” from the “zen”
  • No generic icons
  • No icon mashups that use telephones or location pins

Added two recommendations for icon ideas I wanted to explore:

  • Option 1 – A zenned out animal (I’m not sure which, they all look a bit ridiculous which is good). Maybe one that would ordinarily be high-energy or panic-y?
  • Option 2 – An animal rendered using polygons. I felt it balanced the playfulness of an animal with the angular approach to keep from becoming too serious

These messages were well received by my designers and within hours, new options began arriving. For a few days, I explored how to tweak these icons towards something usable. In the end, my message to designers didn’t bring the results I expected. By being more explicit, I limited their creativity and what ultimately came out was an overcorrection that just didn’t fit.

An overcorrection from my designers after making too specific recommendations.

That said, there were a few diamonds in the rough that made my short list. I spent a lot of time considering how to tweak these with different colors and other relatively minor adjustments. I polled friends and family, but the results always came pretty evenly split.


This is the only new design from that “animal” course correction that seemed a possible fit. I really liked the idea of personifying the inanimate calendar object by working it into an animal.I hesitated on pulling the trigger with this design because it felt a bit too abstract, would a casual visitor recognize this started as a calendar?
You may have noticed I carried this design along for quite awhile with zero changes. This is the element that got me excited about using an animal in the first place!Passing on this design was less about the logo or its potential and more about the designer. After submitting this design, he ghosted me. While the design itself was most of the way there, the inability to make any further tweaks concerned me.
This final option was outside of the animal space, but it showed playfulness and seemed recognizable as a calendar adaptation.My concern in down-selecting this option was whether it conveyed the message I wanted (or any message at all for that matter). Could site visitors get “zen” from this image?

At the end of the day, I wasn’t ready to take on the risk from the owl or zebra designs. After quickly pulling the trigger on the sunglasses calendar, I spent two days on minor design tweaks such as investigating color combinations or changing the sunglass reflections.

Minor design tweaks such as changing colors, reflections in the glasses, and the exact shape of the “calendar” face.

Ironically, within five minutes of committing on the final design, my zebra designer came back. She’d left on holiday immediately after submitting that first design and hadn’t been online to communicate throughout the previous week. Alas, I had committed and it was time to move on.

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Production versus Test Sidebar

I mentioned the logo is an important component of my overall development process. It serves more than just to inspire me to keep building, it just as often acts as a stand-in to protect against error.

The cost of making changes to real data is high, as is the cost born of frustration with iterating on code to fix a web app but the changes just don’t work as expected. I mitigate this by using a standard view on my development site that includes two crucial modifications to differentiate from the active production site.

First, the favicon is modified to stand out. While it is ordinarily composed of just the icon portion of the logo, all development pages include a solid red box which stands out amongst a list of tabs.

Notice the different favicons between development (at left) and production (at right). These are visible in all tabs.

Second, the title of each page is modified by prepending the word “DEV” to each title.

Notice the title visible within the tabs differs between development and production. While this screenshot shows the same page, the non-production site prepends “DEV” to the title.

Finally, the site itself includes a 2px red bar across the top of the site.

These three changes have all but eliminated the possibility of working or testing against a different version of the web app than I intend.

Lessons Learned Summary

I was very pleased with the overall logo designing and selection experience using 99designs and will continue to leverage them for logos in the the future. That said, there were a few considerations that I wish turned out differently.

At the start of the contest, I completed a data collector that gave me the opportunity to spell out what I was looking for. One of the first submissions really stuck in my head and I sent a message to everyone participating in the contest that I wanted them to align towards a different look. This caused the herd of designers to overcorrect while swinging towards the new design. I didn’t care for any of the new designs, but they kept piling on each other.

Even though I was using 99designs exclusively to get access to the design variety only available from crowdsourcing, by aligning so many designers on a single track, it backfired and dramatically cut the number of radically different logo options.

Calenzen fixes all the invitations in your calendar so you never arrive late and frustrated after misdialing. Learn more.