Advisor & Independent Designer
@Twitter @Design & @Wellesley alumna. Politics, design, and cat GIFs: twitter.com/colbay Art & stories: instagram.com/colbay Newsletter: eepurl.com/b-zYaH
Most of us spend more time with our coworkers than we do with our partners or children. You weather the stress of building and launching together. You often share long hours, late nights, lows, and highs, for years on end. That’s a lot of shared experience. This creates a unique tension between professional reserve and emotional intimacy, but at the end of the day, remember that you’re dealing with people, not titles or roles.
Your teammate might not want help, or help from you. What you appreciate when you’re upset isn’t necessarily what they would, either. If you come across a colleague who's visibly upset but they seem to be avoiding attention, perhaps it's not the best time to offer support. One thing you could do is send a message later (if your coworker doesn’t want to discuss the issue, they don't have to respond). Depending on your established relationship, your message could be as simple as “Hey! Want to grab a coffee and catch up?” Then you can feel things out in person, make it known that you’re available to listen. The choice would be up to your coworker on what and how much to share, if they want to share at all. Sometimes they may appreciate company but not want to talk about what is upsetting them.... See more
When we see someone experiencing hardship we’re often eager to offer solutions. This can be well-meant but unsolicited advice isn’t always welcome. It can even come across as pushy, patronizing, or presumptuous. I myself have resented the “helpful” barrage of suggestions when I’m upset. Sometimes the person just wants to vent and already knows what they need to do to address the issue. Sometimes the issue can’t be “addressed” except with time (e.g., a death in the family). The safest thing is to listen. If your presence is welcome but the coworker isn’t saying much, be patient and get comfortable with silence. And when they finally begin to share, please don’t interrupt or offer advice unless they ask.... See more
If you feel your colleague wants to share but doesn’t know how to begin, you can say things like “Want to tell me about it? It’s OK if you don’t. I’m happy to just be here.” Or "Take as much time as you need.” If they express appreciation for your support, and you’re so inclined, check in with them again at a later time too.... See more
If there’s something concrete you can do, such as pick up the slack on a project (transparency and communication are super important here, obviously), do so.
If you’re also overwhelmed or having a tough time, it’s OK if you can’t put someone else first right then. Do what you can without adding more stress to your life (a kind word, a hug, a cookie!) as appropriate in the context of your relationship and circumstance. In extreme cases, you may need to involve someone more appropriate to handle the situation (this can be sensitive, tread carefully).... See more
We often need help, and it's OK to ask for it. Whether you want insight, connections, or guidance, it's important to be courteous. The folks you reach out to are likely higher-profile, industry veterans, or both, with busy schedules. They're going out of their way to give time and attention to you, a stranger, while expecting nothing in return. Here are a few suggestions for how to ask for someone's time, and how to engage when you take it.
Ask a trusted friend or colleague to introduce you. A personal introduction starts you off closer together; anything to reduce formality is good.
People don't have time to read emails. Quickly thank the person making the introduction and indicate that you're moving them to bcc. Always do this to let the introducer know that you've initiated conversation, and to relieve them of more email. State who you are and why you want to meet in one to two sentences. Ask to meet for coffee at a time and place convenient for them. Say thank you and sign off.... See more
You may append additional context if you feel it'd be helpful. Bullet points under clear headers are great. An example is "A LITTLE MORE ABOUT ME" which could lead to a short paragraph. Then "WORK" which could introduce a short list of links: LinkedIN, online portfolio, writing samples.... See more
Sometimes emails slip through the cracks. If you don't get a response in one week, send one more email to check in. I've always been happy to get polite pings when my time is being asked for and I dropped the ball on responding. Likewise, I've never gotten negative reactions when I'm doing the reminding.... See more
Usually the person's assistant will take care of calendar, but if setting time and venue directly, suggest a time yourself first. It can feel like a lot of work for some people to initiate the scheduling, so take this burden off their hands and put a stake in the ground. Venue should be convenient to the other party; they can set that. Reserve 60 minutes in your own schedule but send a calendar for no more than 30. Never assume you have a full hour! It can appear obnoxious. If a phone call is the only thing possible, take it.... See more
Be understanding about rescheduling, sometimes quite last minute. There’s a reason you’re asking this person for their time. You’re not the only one who is asking for it, so don’t assume you’re a priority. It's a good idea to share your phone number or open DM information in advance so they can contact you more easily while on the go. If there's a month or more between correspondence and the meeting date, send a quick note a few days before you meet.... See more
Better yet, get there 5 minutes early. If you're a chronic fashionably-late person, squat at the cafe beforehand to get some work done; then you're already there hours in advance.
I cannot stress this enough. It may seem like common sense, but I can't tell you how often people bald-facedly take hours of someone's time at a cafe without even offering to get them a drink. It's shockingly bad manners. Whether you actually feel this way or not, this behavior says that you think the person's time isn't even worth $5. It's a small gesture that costs you almost nothing. Just do it. By the way, this applies even if the invitee is a potential employee or contractor. If you are the asker, you are the beholden.... See more
Thank them for their time and follow up via email. A quick summary is good for record-keeping purposes. Mention action items, if any. If there's anything you can do for them, such as making introductions yourself, offer.
When someone asks you for your time, give it generously. It's good for the universe.
Start with a conversation (or two). In-person is great but at this juncture phone or video chat is completely fine! Introduce yourself and frame your expertise, but let them do most of the talking. Before the meeting it often helps to think about the questions you want to ask ahead of time about schedule and expectations. If it doesn't seem like a fit at this time, kindly tell them so. For instance, you might be overqualified for the specific project. Or they might need a lot of pixel-pushing and you prefer to focus on strategy. In this case your time as well as their money would be better spent if they went with someone else. Give them a referral if you're able. Perhaps you're inclined to help out in an advisory capacity in the meantime.... See more
If there's good chemistry and alignment, don't be afraid to be proactive about how you'll spend your time together. Lead with what resonates with you: your client wants a job done well, and you want the job to be enjoyable as well as challenging. These things should not be mutually exclusive. If you get the sense that a fledgling team is overwhelmed with a disorganized system, you can offer to help review their information architecture. If they're struggling with a dull brand, perhaps you can lead a workshop to kick things off in a new direction. If you like doing these things, and they would greatly benefit from your expertise, why not prioritize them in your time together? Clients are so burdened with their own tasks that they're often relieved to have someone else take the lead in defining the collaboration. Look for open doors, and step through.... See more
It's easy to for the client and the consultant to have startlingly different understandings about something that can seem so basic. If you have the slightest doubt, ask. A good way to get clarification is to repeat back to them a summary of what you think you've heard so far, or your version of a complex product detail they just explained. Likewise, be very clear about what the client expects to have in hand at the end of your time together. What form will the deliverables be in? Will you also be handling production? Don't assume that "half-day" means 4 hours, that they'll pay for expenses incurred, or that there won't be travel involved. Spelling this all out will force them to be specific about, and you to be clear on, load and scope. I usually put my requirements and work proposal in a 1 to 2 page letter of agreement. The client and I revise as needed, together. The more established clients will have their attorneys incorporate it into their own legal documents which will serve as the final contract.... See more
So you’re thinking of going independent. Are you able to explain why freelancing appeals to you, clearly and succinctly? What does that life give you that a salaried one can’t? People become freelancers for a host of different reasons: family, health, artistic pursuits, the desire for more autonomy. Freelancing isn’t easy but can also be extremely rewarding. But those rewards depend on your priorities, what you’re willing to give up for, and how you plan to pursue, them. Paying the bills is only a part of it. You don’t need to have all the answers up front, but it’d be wise to have an idea of what you want the big picture to be before making the shift. List out your priorities and take a good long look. How does freelancing support or complicate their fulfillment? Be brutally honest with yourself.... See more
Write down the pros and cons of salaried versus freelance life. Freelancing isn’t just about choosing which day of the week will be Sunday, or working in your pajamas. You’ll have a lot more to take care of than just client work. You’ll pay taxes four times a year instead of once. Healthcare will cost a lot more. $500/mo isn't unheard of for single coverage PPO (high deductible, no dental or vision) even as a healthy young person with no pre-existing conditions. Get creative in navigating this brave new world. Taken one step at a time with some forethought, it can be done. If you’ve a domestic partner who can add you to their plan, great; Stride Health is a good resource; an FSA card is worth looking into. You’ll pay for all of your software, tools, conferences, and classes. You'll be your own HR, salesperson, CEO, manager, and PM. You'll have to deal with awkward situations (like clients who don’t pay on time). Expect to make mistakes, iterate on structure, and refine process. Does this give you cold feet or feel like an adventure? Pay close attention to how you feel as you assess what freelancing entails.... See more
The less of a black box it is, the less stressful it'll be, and you’ll be able to reserve more of your headspace for the actual work of setting yourself up as a freelancer. You can start by sitting down to compose key questions, then asking some veterans. Why did they start? What did *they* do when a client balked at their rate? What’s the biggest lesson they've learned? There are a ton of freelancers on this platform (👋) and others like Twitter. Reach out, come prepared with questions, buy them coffee. Listen closely and don't forget to thank them. Striking out on your own can be scary, and it helps to hear others’ personal stories while building on their knowledge.... See more
Money will no longer magically show up in your checking account every two weeks. Sad, I know. Holidays and weekends may not seem so shiny anymore, and the idea of taking vacation might be stressful, not fun. It's normal to be stressed. Do everything to mitigate this stress. Take a look at your savings, for a start. A well-cited rule of thumb is at least 3 months' worth, but I would recommend a year's worth (or more) for emergencies and dry periods. No more 401K matching either so you’ll need to set up alternatives (IRA, SEP-IRA) for retirement as well.... See more
How are you going to get gigs? You can put yourself out there among the hundreds in a sea of portfolios, but ideally you get introduced to projects through personal connections who understand your skillset and can vouch for your expertise. Without a strong network, you may be subject to taking on unedifying jobs purely for the sake of paying the bills, and if that’s the case you may as well keep the security of a regular paycheck. Prepared to put out a few feelers? Put a portfolio together. Get some endorsements in place. Reach out on Twitter or other networks where you can get seasoned folks to help you spread the word. Many often can’t take on all the gigs that come their way so they’re relieved to pass on some overflow.... See more
Once you’ve done your homework, squared yourself with the risks, balanced your books, and can clearly articulate why you still want to freelance, take a deep breath and come on over to the dark side. So maybe everything isn’t as organized as you’d like. Maybe you have only a vague whiff of a Plan B, no partner, nor a mountain of savings. But you still want to do this! Go for it! What’s the worst that can happen? So you make some mistakes, get some curve balls, return to being on a payroll. You might realize that freelancing isn't for you, or that it’s not for you *yet.* It’s not a crime to crave a regular paycheck, cheap healthcare, or paid vacations. But if you don't give it a try, you won’t know the joy that comes from, and whether it’s worth, steering your own ship, when and how you’d like.... See more