Category Archives: Career Development

Strategies for Side Project Success

Strategies for Side Project Success

Side projects can be a vehicle for personal growth and discovery. Even when the result isn’t long-term financial gain, the education and experience that comes with a new product launch is always rewarding.

Side gigs have allowed me to learn new skills, meet smart and interesting people, and explore aspects of business that my full-time job does not offer. Those who freelance or work from home often generate ideas for side projects, each a new rabbit to chase down a hole.

But should you follow? The answer is a resounding “maybe.”

With careful consideration, respect for the work that pays your bills, and the ability to stay focused, you can pursue a side project successfully. You can—and should—follow that rabbit, as long as you do so with patience, intention, and discipline.

Strike a balance

Pursuing a side project while another gig pays your bills is tough. Many people talk about finding the time to work on a project, and that’s a problem. You don’t find time for something like this: you designate it.

If you have an hour after dinner to pursue a new venture, write it on the calendar and make it an official date. It’s harder to shrug something off if time has been set aside for it.

Note that I suggested only designating an hour. It’s not much time, and that’s intentional. Your billable hours should be the priority, even when an idea is new and exciting. Take it slow so you aren’t robbing yourself of paid work.

Make a plan

Any successful side project should start by clearly defining the idea. I do this with a mind map, which is like a semi-organized brainstorm. It’s an excellent way to get all your thoughts, ideas and reflections on a single topic written down for later reference.

Start by writing the idea in the center of the document and then branch out all of the things that help define it and make it into reality. When you’re done, it’s easy to see all of the components of your side project in one place. From there, you can put them into categories and get to work during your designated time.

Define essentials and enhancements

Ideas usually start flowing freely once you’ve defined the new project and put it into a mind map. It’s a great feeling, but it’s important to be mindful of what’s necessary and what’s just fun.

I recommend using two lists to separate the two. Name the first “Essentials” and use it to record what must be in place to get a minimum viable product up and running. The result is a clear roadmap getting you from where you are to where you want to be.

Name the other list “Enhancements” and use it to record things that are fun features to have like that cool animation, integrated Twitter sharing, and so on. Only turn your attention to Enhancements once the Essentials list is completed.

This takes will power, but remain strong. You can delay that gratification.

Beware the enthusiasm bell curve

It’s normal for enthusiasm to taper as you work on the more mundane parts of a side project. If it’s a business, this could include opening a business checking account, determining the cost of the product or service, registering your business, and so on.

This is a dangerous time because it’s usually when that second idea pops into your head. It’s tempting to turn to the new idea and leave the original plan in the dust, but abandoning ideas halfway through is how side projects never get finished.

Plus, take comfort in knowing that you’ll feel the same way about the second idea once you’re halfway through launching it, too.

Know when to put it aside

Sometimes a brilliant idea comes to you at the exact wrong time. If you can’t dedicate time to work on a side project right now, it’s still possible to seize the opportunity by:

  • Filing it for later. If a new idea appears when you can’t work on it, store it for later. Put a reminder on your calendar on an appropriate date in the future.
  • Grabbing the domain name now. If you must delay work, grab the related domain name now before it gets scooped up.
  • Identifying the small steps that you can do now. This will often result from your mind mapping session.
  • Conducting relevant research. Read books or subscribe to a relevant podcast to listen to while in the car or during downtime. There’s a great book called Making Ideas Happen by Scott Belsky that addresses much of this.
  • Working on behind-the-scenes planning. Think about everything that must be done before you can begin work. When you’re ready to pick the project up again, all of the planning will be in place.

The keys to planning and managing side projects

Side projects take focus and planning but can be hugely rewarding—both financially and for personal growth.

Maintaining momentum when you begin a side project is key to getting it across the finish line. Break tasks down into small chunks, set attainable goals for the week, and create a series of small wins for yourself.

As Jerry Seinfeld says, don’t break the chain. Work smart, and good luck.

Demystifying Public Speaking

Demystifying Public Speaking

The fear of public speaking is widespread, and well known. However, there’s no denying that presenting to an audience can help advance your career, build your network, and sharpen your skills. So what’s an aspiring speaker to do? How do you get from “cool idea that I want to share with people” to the stage? There’s got to be a roadmap, right?

Thankfully, the fine folks at A Book Apart have it covered. The Authentic Jobs team are big fans of ABA, and we’re ridiculously excited to be able to share an excerpt from “Demystifying Public Speaking” by Lara Hogan, VP of Engineering at Kickstarter.


Get in the door

You have two routes to speaking at an event: submitting a proposal or being invited. When you’re starting out, or if you’re switching gears to a new topic, you’ll likely embark on the submissions track. Let’s get excited about filling out some forms!

Submitting a proposal

Each conference has its set of questions about your talk content, format, and you, the speaker. Organizers use this information to figure out if you and your talk suit their event and audience. For example, a typical O’Reilly conference might ask for:

  • The proposed title
  • Both an elevator pitch and an extended description of the presentation
  • The topics you’ll cover
  • A biography and headshot
  • A video of the speaker giving a talk
  • Any anticipated expenses, like travel reimbursement

Once the submissions are in, organizers cull them and decide what shape the conference should take, based on industry trends and key takeaways for the audience. Some conference organizers read all of the submissions themselves; others arrange panels to gain more diverse perspectives. As they consider contenders, organizers put themselves in their audience’s shoes: what does that audience want to hear?

That’s a question you should keep in mind as you create your pitch. Sarah Mei does a fantastic job exploring the sales aspects of writing a proposal in her article “What Your Conference Proposal Is Missing”:

People don’t go to talks for the content. People go to talks because they think they’ll become more badass. So help them out with that! Make it easy for them to imagine their newfound superpowers, and they’ll match your level of excitement. 

But let’s back up and return to you. Have you ever looked at a CFP form for your dream event—the one that always has the best lineup and most fun participants—and chosen not to submit? If you said yes, you’re in good company. Maybe you share some of the fears people noted in my public speaking survey:

  • “I’m afraid I’ll fail to tell people something new and interesting.”
  • “What if I choose a topic that’s been done to death?”
  • “No one would want to listen to me talk about anything.”

Don’t take yourself out of the running before the people organizing the event have had a chance to look at your proposal. It’s literally their job to find talk topics that will be relevant and enticing to their audience; you can help their cause—and yours—by choosing conferences whose audience and focus lines up with yours.

If you’re still a little unsure or plain stuck, get a second pair of eyes on your draft! Ask a colleague or friend to give feedback on questions like “Would this topic be helpful for this event’s audience?” or “Is this the right level of depth for a proposal?”

Content Structure

Coherency—avoiding word barf, being articulate—is a natural concern. Many survey respondents feared “not getting points across” or “being boring or rambling.” One person worried about “making the story flow well enough…finding the balance between helping people along and having them learn things on their own.”

Creating a solid structure for your content is the best way to guide your audience through your topic—structure helps set expectations for what’s next, strengthen your arguments, and keep folks more engaged. It also gives you a foothold if you lose your train of thought.

My friend Ed Davis taught me how to put together a presentation that tells a story. Early in drafting one of my first talks, I’d written what I thought was a decent deck: I’d listed the steps involved in making a website faster, with every point backed by plenty of technical detail—think lots of charts, lots of code samples. Ed had some gentle feedback: though the information was clear, he thought my message would better stick with my audience if I could walk them through the context—what made the work important. He suggested I take the audience on a narrative journey:

  • Landscape: what exists. In my presentation, the landscape was “A lot of web pages load slowly.”
  • Analysis: what you, the presenter, want to highlight for the audience about that landscape. “This poor performance creates a poor user experience.”
  • Problem: the core issue based on your analysis. “Studies have shown a correlation between a slow site and decreased engagement, which isn’t what website owners want.”
  • Options: what we could do. “We could ignore it! Or we could speed up the site in these ways.”
  • Solution: the best option and how it works. This was the bulk of my talk, walking through all the ways to improve front-end performance.
  • Reasons: why the audience should believe you. “Completing this work sped up the site by 35% and increased conversions by 7%.”
  • Bigger idea: why this concept matters even if it seems irrelevant to an audience member’s work. “Even if you think your site is fast, what’s the experience for your users on slower infrastructure, outdated mobile networks, or older devices?”

I’ll be honest: I didn’t think much of this new narrative. I was building a slide deck on techniques to improve page load time. Wouldn’t people—people who were choosing to see my talk—already know why performance was important? Why should I add the landscape, the bigger idea? Enough fluff—don’t people just want the how?

Thankfully, I decided to give this narrative structure a shot (uncomfortable feedback is often a gift). Immediately, the presentation was so much better: the story helped draw in the audience, and the logical progression meant they could follow my flow and trust my arguments.

Developing this presentation structure also forced me to ask myself: Why am I even speaking to begin with? Nailing down the bigger idea—what I wanted the audience to leave with and think about after they went home—was crucial to making my presentation memorable.

This sample narrative structure won’t work for everyone, of course. You have plenty to pick from; a couple include incorporating a backstory or flashback, or following the Hero’s Journey. Your topic may work best with more case studies, graphs, or live demonstrations.

Whatever tack you take, think about the talks that have resonated the most with you. What kind of narrative or structure did the presenter follow? Why did it work so well? How did they make their arguments stick?

The most important part of your presentation is what happens after; use your presentation to lead your audience to both inspiration and concrete next steps.

Skipping the line

Once you’re on the speaking circuit, you begin to get invited a lot more to give talks, rather than submitting a proposal through the normal channels.

I’ve received invites via Twitter direct messages, out-of-the-blue emails, and connections from trusted friends. Some invites include lots of information about the conference and what they hope I’ll bring to it. Sometimes they include a list of other speakers who’ve confirmed their talks, as a way to convince me that I want to be on that roster.

An invite doesn’t automatically mean you’re in; some organizers extend invitations to submit an idea, while others ask you to give a particular kind of talk—which you might not want to do! Feel free to see if they would be interested in a different take.

For instance, as I’ve done a lot of web performance talks, organizers often invite me to present the same talk at their event. Some places will ask me to change the length of the talk (I can tell you it’s rough to cram a 90-minute workshop into a 30-minute lecture!), and others ask for completely new material.

As ever, ask questions in turn. Event organizers want and need you to succeed—get their perspective before you submit your pitch. I’ll check if they’d prefer a 101-level topic or more depth; or I’ll see if they have any subject gaps in their lineup they’d like me to cover. Recently, I spoke at a conference that attracts more designers, so I refocused my performance talk to include design considerations on site speed. You want to go for something that feels good to present and is equally as fulfilling for your audience to hear.

You won’t get invitations to every conference you want—and it’s okay. Keep submitting, whether it’s through a CFP or your network. The more practice you get with sending proposals, the more you can learn from the process and event organizers about what makes a winning pitch. Follow up with any rejections (we all get them!) to find out what wasn’t quite the right fit, and see if that feedback applies to your next submission. Maybe it’s as simple as “We already had three proposals on the same topic,” or as helpful as “This wasn’t the right technical depth for our audience.” Learning and iterating is the key to each step toward the stage.


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