Name: Kelly E.
Location: Upstate New York, USA - quite far north, on the Vermont border (Middle of nowhere!).
Business Profiles:
Upwork profile
LInkedIn profile
Getting Started & Freelancing Journey
- How long have you been freelancing?
I've been working for myself for almost all of my adult life... with occasional part-time "real" jobs to supplement the income, but mainly, self-employed, in various capacities. Upwork calls it freelancing, but is it really so different from "self-employed"?
- What inspired you to take the leap into freelancing? Was there a specific "aha!" moment?
It seems that I've got an entrepreneurial gene. I was already making flyers and pitching my skills to "prospective clients" when I was around 11 or 12 years old—lawn services, then housekeeping, then babysitting... so I've been taking the leap my whole life.
I love helping clients reach their goals, I'm not afraid of the risk, and I (sort of?) love looking for clients!
- What is your main skill/service? How did you find yourself focusing on them?
Main skill: Brand identity development—helping clients to grow through great brand strategy and execution. I help brands land punches!
Services: Brand identity audits/ research/ strategy; target-market focus, messaging, naming, UX, print & digital graphic design, market-focused copywriting. Boosting brands and breaking through the clutter of today's consumer landscape.
When I began my self-employment as an adult, I was an interior designer and custom furniture designer.
As a fledgling interior designer, I also did all my own graphic design and self-promotion (ads etc.), and I had a few business clients ask if I could do their design & marketing work.
So I began to pivot from the experience of walking through interiors, to the experience of the entire brand. And I called myself an Experience Designer—a term which isn't used as much anymore as it was 20 years ago, but it really describes my highest ambitions for what I do for clients, better than any other. I want to help businesses engineer the best possible brand experience for their customers, from their name—the most important ad they'll ever write—to the ease of using their website... hopefully to get customers to cry with relief and throw money at the company!!
(My university degree is in interior design, with a concentration in graphic design—but I went back to get that degree after I had already been working for myself for a few years. It meant so much more to me, since I had already been using those skills out in the real world!)
Platforms, Skills & Services
- What platforms have you found most effective for finding clients and building your freelance business (e.g., Upwork, LinkedIn, personal website, referrals)?
I got my online business journey started with a business website, a blog, and a lot of networking outreach. That worked well in the 2000s, when everyone and their uncle didn't yet have a blog or a website. I was pretty well-known in the branding/ marketing community, and got some recognition in places like Ad Age. And my wonderful clients referred me to other clients—some local, some national and international. I like to say I've worked with clients from Silicon Valley to Sydney!
Other folks I started along with had their blogs & websites take off, and that helped their businesses grow exponentially... but mine, maybe because I focused on smaller businesses where budgets are perennially tight and jobs are more likely to be one-offs (but where I've always felt I can help the most), stagnated. With a devoted, but not strongly increasing, readership and client base, my personal sites were great for a while... then not as much.
Long story short: after some time off, I gave Upwork a try. (My Upwork story is a little off-kilter—I didn't originally think I was going to do brand work there! —but we'll skip that story.) It seemed to have excellent potential, and I saw good growth for a while... then, well—like a lot of others, I've watched Upwork tank.
Investigating LinkedIn now—so far, a very affirming place, with lots of professionals who understand me, but too soon to say whether it will be a good fit for a freelancer like me to find work.
Originally: Strong growth with little, or just-right, outreach efforts. From zero to part-time income to "I can see full-time income approaching" fairly quickly. Good clients. Good projects. Invites! Reasonable ROI on sending proposals.
Then: Right off a cliff, when what I presume was a combination of algorithm changes + opening the freelancer floodgates, destroyed the character and the experience of Upwork in just months.
Now: Spend too much time wondering why I spend any time on UW, combined with occasional flashes of the old site (good clients, good interactions...) that suck me back in again.
This is an interesting question. I don't specialize in working with one industry, like hospitality, and I don't specialize in one output, like social media posts.
But I do specialize: In helping founders and businesses to audit and design the overarching verbal and visual message that their brand displays to the world. Designing the customer experience. "Meh is murder," I say, and too many companies are stuck there—delivering meh and wondering why customers don't beat a path to their door. Pre-launch or ten years in, I help them figure out how they *are* or why they're *not* connecting, and what would make their vision for the company shine for the right customer—and then I help them to aim for that vision in every customer interaction.
I do smaller jobs, too, but always with that focus on HOW DOES THIS WORK CONNECT THE PRODUCT or SERVICE TO THE MARKET? I won't design even a "simple" logo without making sure the client and I are clear on who... why... and whether we're aiming in the right direction.
The client's business goals & focus, come before all. I can't stand to see a client waste their budget making something "pretty" or "trendy" that doesn't connect with their ideal customer at all—and I really believe my clients appreciate that I'm obsessed with *their* success.
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Beyond your core skill set, what "soft skills" (communication, time management, etc.) have been crucial to landing and retaining clients?
Communication: I've been doing this for a pretty long time, off-Upwork and on. I can tell clients how a project will (or should) go down to the letter, so there are no surprises. I know that anxiety loves a void, so I'm always keeping in touch during the project. I really love helping businesses grow, and I think that shows in my communication.
Time management: One thing I've carried from my interior design days to now is that any project will find a way to take a lot longer than the hours or days/ weeks you allotted to it... whether that's because the client doesn't have time to approve a step, or because research causes a change of direction, or because some darned piece of software updates, and I have to find where that one thing went! So I always make due dates further out than I think we'll need. I'd rather deliver early than make a client wait!
One: I've been doing this a long time, so I know from hard experience how long things will take. I even know where the likely hiccups are. Be thorough when explaining the steps in your process and the hours involved in getting the results they asked for. Be sympathetic to their budget and their needs! But never shy away from having this conversation early. (On UW, clients often have VERY unrealistic ideas of how long a project will take!) If a client doesn't want to work with me because I told them honestly how long XYZ takes, then they're better off working with someone else and finding it out for themselves.
Two: For me, I never go more than two days max without sending an update. Preferably daily, even if it's just a really short note (but sometimes things happen). And I tell clients that they can expect updates at least every other day. When someone can't look over into your office and see you, they don't know whether you ARE working... or whether you're STUCK... or whether you've decided to GHOST them. Never let that fear creep in!!
Three: Scope changes. *sigh* This is rough because in my experience, some clients don't see that "Can we try it again in a totally different way" IS a change, even though we agreed to 3 variants or whatever. They've been talking to you every day for a couple of weeks, and it's just wondering-out-loud on their part. So I walk 'em right back to our very detailed original conversation, and as nicely as I can, I say "Yes! We can absolutely try it again in a totally different way. But as a reminder, our agreement of 32–40 hours and completion by the end of March will change if we do the fourth step all over, by [this] much... and we'll want to be clear in advance on why, and what outcome you expect from repeating the step, so we can get you the results you need to be psyched to keep going from there."
Kind of answered above in the "evolution of my business" question: I began as an interior designer, later pivoting to brand design/ customer experience design at the request of business clients who liked the design and promotional work I was doing for my own business.
Are there any emerging skills or services that you see becoming increasingly valuable for freelancers in your specific niche?
Recently I see a lot of call for animation design and motion design for business. They have value for businesses that need them (and for freelancers who provide these services!), but as someone who looks at the big picture for clients, I believe they're often experiencing trend-FOMO, while not really considering whether there's any business case to be made for motion design (etc.) in their own growth plan. From a freelancing point of view, the jobs are definitely out there, and they generally pay better than many design jobs.
Another service that's top-of-mind for job-listers these days is social media post writers and designers. In another era these might have been quarter-page magazine ads—if you specialize in making business ideas pop in fun and easy-to-digest ways, there are plenty of prospective clients looking for you right now. If you go this route, learn to talk about your posts' value in business terms, so you don't become "one of many" doing pretty pixels for clients.
And not to be outdone on trend-FOMO, there are boatloads of ads asking for "AI-graphic-designers." Why do clients want this? Is there a business case for it? Does it get them better outcomes? Just between you and me, I suspect these are mainly people hoping to get something for as close to nothing as possible, and they heard AI is the way to get design on the cheap without having to hire their high-school-aged nephew. So increasingly valuable, No. But increasingly prevalent? Yep.
Originally on UW, I was increasing my rates every few jobs. More evidence of five-star Upwork completed = more evidence that I'm worth... what I used to make "on the outside." So I began a little low, but not unlivable, and gradually increased.
I'm at a sticky point for my field on Upwork right now, yet I really believe I'm not at market pricing for my experience level and the value I deliver to clients.* This puts me in a quandary—ignore the UW consequences and raise my rates even though at the moment, I'm *not* seeing steady Upwork growth?
Existing vs. new clients—Upwork has a really annoying feature now where we have to tell new clients... before they are clients... whether we'll ever raise their rates. Lots of people have chosen to say "never" in the fear that the idea of future increases will cause prospects to run away. I've chosen to say that there will be annual increases, in the hope that anyone who thinks they WILL enjoy working with me for longer than a year, but WON'T be willing to pay a 5% increase, will stay away. In my opinion, if that's the sticking point, before we've even begun—it's best if they do run. (To date, I haven't had anyone even mention it.)
These are issues we all deal with as freelancers/ self-employed people. What to charge is a bit art form, a bit divination, and a bunch of hard math.
*Before submitting this questionnaire, I did decide to increase my rate. Art form, divination... and little nudging on our forum!
Absolutely. Just like I have a blueprint for proposals, I have a blueprint (of sorts) for interviews, whether through Upwork messages or through Zoom calls. I've done this so many times before, and many of my clients have never tried to up their game by hiring someone like me—so I try to put those clients at ease by keeping us to an agenda of sorts, that will answer their remaining questions and give them confidence to proceed. (It gets funny when they have a strong preference to do our initial discussions in a very different way, but in that case I just roll with it.)
The client is an expert at what *they* do. I hope my gentle steering through our early discussions, in particular, helps them to feel assured that I'm the expert they're looking for in my field.
Oh, you want to know what my particular blueprint is?
I'm giving away all the secrets, here. (No guarantees, friends. I'm not an expert on the workings of Upwork. So maybe I'm just a cautionary tale!)
Brief. Friendly. Helpful. Professional. That's the basics!
First thing: If at all possible, I keep conversations to Upwork messages only. Strong preference for having everything written out (that way there's a complete record to refer back to in case of any later confusion or mis-remembering)... born of long experience. If it's not written down, it practically didn't happen. I want to reassure the client that I'm as good as my written word—and yes, I want them to reassure me.
If we have to do an initial Zoom call so they know I'm not a bot, okay—but they will be getting a written review of the call from me in UW messages immediately afterward.
And I never, ever give Upwork prospects *or clients* any "outside" contact info. I pay UW good money to be my walled community and give me some safety. If we communicate off-site, I'm just shooting that safety full of holes.
And also from long experience: I let clients know that I don't do meetings during contracts. When they're paying me by the hour and I say, "meetings waste our time," people are usually on board. When we each take a moment to compose exact what we want to express and send a message, there's clarity and efficiency that helps the entire project.
(Oddly, when I worked for myself through my website and blog, no one ever asked for a call. Ever. For some reason... the volume of freelancers, maybe? People like calls on UW.)
Then if possible, I do a brief investigation of the client's company before the interview or continued messages. I want to be able to understand their needs more than I did at the time of the proposal, and I want to be able to ask good questions.
I do NOT give any more information about the specific direction I'll be taking their work, when we're pre-contract. They already have my working process and time estimate, from the proposal itself. Too many job-listers on UW will pump 17 different freelancers for information and then not hire anyone, because if they put it all together they've got everything they wanted for nothing! If you haven't experienced that before, beware. It's out there.
After we know each other a bit better, I reiterate what the first steps will be once we have a contract in place, I thank them for their time, and I leave them to their decision. Again -a conversation that goes on too long, can be one where you give away part of what should have been paid work.
Tools & Strategies
1. general (project management software, accounting tools, communication apps)
- Microsoft Outlook "Notes" for keeping copies of/ notes from proposals and projects (I don't think Notes is available anymore? I have an oooooold copy, and I'm completely tied to it for my workflow)
- Excel for slicing and dicing my Upwork stats
- Zoom if we must (but I find meetings to be big time-wasters so I avoid if possible)
- and I've made my own blank project-management calendar in Word, customized to the work I do; each project gets its own calendar, so I can keep a broad overview of past & next steps, communications, ideas, deadlines, etc. (then details are held in that projects "Notes" doc or in deliverables docs)
2. niche-specific?
- MOST essential tools: pen/ pencil and paper... and getting AWAY from the computer to ideate/ design/ write for stretches of time
- Adobe suite, especially Illustrator, Photoshop, and InDesign
- Quark XPress (though lately I'm doing more in Adobe InDesign so Quark is falling away a bit)
- a little piece of software called Paparazzi! for capturing full-page screenshots (client or research/ competitors)
- occasionally: Figma, LogicPro, Final Cut Pro, Sketch, SketchUp, AutoCAD
Sure! I'll paste it first**, then talk about the project briefly.
**All text (c) Kelly E—please take lessons and ideas from it, not actual copy!
(First things first... I'm not in MD right now—I'm in New York State—but I lived in DE for almost 20 years and I'm very familiar with the mid-Atlantic business climate. Hope that helps with the regional issue!)
Yes—I would love to work with you on the logo for your rising business! Is it time for a designer who obsesses over the successes and the pitfalls just like you?
After reading your job listing, I’m curious to hear more. Helping companies to grow through great strategy and execution is my passion. My work includes: brand strategy/ growth planning, naming and tagline development, customer journey/ sales funnel mapping, graphic design (logos, web design, printed materials, wearables...), user interviews/ testing, website audits/ experience optimization, blog and copywriting, and site architecture.
How it works:
—Once we *agree on the design direction and any must-haves* (like “I hate red” or “I love blue”)
—I will take a few days to think it out and then *present 3 roughs to choose from*
—If necessary, we’ll *talk about particulars* of the chosen rough (“I love the layout but not the doo-dad in the corner”)
—Next I'll deliver *second roughs, showing 3 potential treatments of the chosen rough*
—I’ll *complete and deliver your logo* according to what we’ve discussed
—It’s usually not needed if communication has been good, but once the rough you’ve chosen is fleshed out, I do include *2 minor revisions* if necessary
—Note: the listing was a little unclear as to what else you might need in the full scope of your project. Things you may be considering, which we can add to the project if needed: brand focus work; naming/ URL consultation (your name is the most important ad you'll ever write!); tagline development; further graphic design, including your business card, letterhead, merch, presentation/ marketing materials; your unique Value Proposition, Mission, and Vision Statements for use in website copy and in maintaining focus; website copy, consistent with your pinpointed tagline and Value Prop; website wireframing/ navigation/ design recommendations. Let me know and I can give you an updated estimate—the process of adding these elements to the project is pretty smooth, once I'm already “inside the head” of your Ideal Customer via the steps above.
A straight logo design project like yours should be completed in about 7–10 hours, and can be delivered in about 2 weeks—well within your timeframe. If you need a rush job and we can be sure of smooth communication, your design can be delivered in fewer days, with less mental “marinating” between work stages. Just let me know.
Thanks for reading my proposal. I’d love to hear more about your project and dig into it. Giving you the edge with a fresh approach to your Ideal Customer would be a real delight!
Looking forward to hearing from you,
Kelly
P.S. I’m sending along my “brand”-new branding book, based on over 15 years of work helping businesses to get the word out—and a sneak peek of work for my next one! I hope they'll give you a feel for the joy in finding your edge and communicating it to your audience.
This one has all the essential elements—
First, show that I read their listing, within the characters that will show in the preview.
In this case, they had asked for someone in Maryland, U.S., which I suspected wasn't needed for a logo design project—so I applied anyway, but addressed that requirement and why I'd be just as knowledgeable about the area as if I were there.
Next, talk about their needs, from their perspective. Yes, every business owner obsesses over their successes and their pitfalls. And every business owner wants to grow through great strategy and execution. Yet a couple of phrases like that can make someone think, this person gets me! (Which is true. I've met so many folks like them that I *do* get them!)
I haven't seen other UW proposals but my sense is that not a lot of people take the time to think from the perspective of the person on the other side of the screen.
Then, answer all the questions someone who has never hired a person like me will have about how the work progresses.
—How much will they be involved? (Lots.)
—What if they feel like we still didn't quite nail it? Do I stick them with something subpar and run? (No way—between their involvement all along and revisions if needed, they're going to have what they need.)
Hopefully, they're imagining themselves working with me at this point, so now, I suggest that we could add other elements to the project, and I help them think about a whole suite of possibilities that would all tie together and take some of the weight of growing their business, off their plate. This section is customized to the business or industry, if the listing gave me a clue... in this case, it didn't, so it's my standard suggestions.
Before wrapping up, I answer the big one: HOW MUCH? Upwork lists my rate, so all I have to do is say how long this project will take, and the prospective client can do the math.
Last, after I've signed off I always do a P.S. In long-form copywriting, it's an old maxim that people read the P.S. more than they do anything else (and some people even read the P.S. first!), so I make sure my P.S. continues the positivity and focus on their needs, while encouraging them to open the attachments which will demonstrate visually, what they'll get from working with me.
And this proposal worked exactly as well as we all wish our proposals would:
Not only did the client hire me for the logo, but my prompting about potential add-ons helped turn a 7–10 hour job into a comprehensive, 85–120 hour branding wish list.
Invites used to be a lot more reliable... now they're rare and often scammy, so I can't rely on them. Through highly targeted Saved Searches, I save myself from looking at most of the jobs on UW. I scroll through my Saved Searches at least once most days, pulling out the interesting jobs into new tabs until I'm done seeing what's new. Then if one or more was SO strong I'm still thinking about it, I send a proposal right away; if not, I may walk away and do other work for a while, and come back to the tabs in an hour to see if any still seem interesting, and send proposals then.
Good proposals take just a little money, but significant time, even if you have it down to a science—I don't like to waste time or money, so I make sure I can really imagine myself kicking butt for the prospective client before I craft a proposal to them.
The "science" of proposal-writing, for me, is this:
There are certain things that come up frequently in the listings or inquiries I respond to. So I have standard segments that I plug in to answer as many unspoken questions as possible: How do you work? What have you done before? How will this help me? etc. The intro is customized to the individual proposal, and there's some customizing in the middle to respond to exact requirements. Some of these "segments," I've been using successfully to help clients envision our work since well before Upwork! But I also tweak language and details, to keep things fresh and to try to increase response rates.
Because each proposal is individualized, it takes me between 5 and 20 minutes to get one proposal out the door. But if I were starting from scratch each time, I'd never get anything else done in a day!
Submitting proposals: In the heyday, when Upwork was really working well for me, way less than one a week.
As it began to fall off a cliff, when I couldn't figure out why leads were drying up and I thought more effort would = more results—usually more than 5 a day, M–F.
When I became thoroughly disgusted and realized every effort I made was just zapping my bank account (Connects) with no true ROI, I went down to less than one a week again. A few weeks here and there, I would try again just to see if anything changed. It hadn't.
This year (2025), I've been testing the Upwork waters again (about 10–20 proposals/ week), and seem (?) to be seeing more views and contacts... but none of those dopamine-fueling metrics count unless contacts turn into jobs, so I'm not sure how long I'll play the use-Connects-for-no-reason game this time.
Proposal success rate has varied so much over my years on the site that it's pretty meaningless. Originally, 65% or more. Since the floodgates opened, way less than 5%.
Keep in mind: *I* haven't become somehow worse at what I do, and I've even added some pretty cool work & clients & recommendations to my roster—so I like to think I should have become *more* appealing over these years.
That dramatic change in outreach-to-success ratio, is why I've become disgusted. From where I stand, Upwork's not even the same site anymore.
Kind of answered above: I want to have a rate that pays me fairly for the level of work I do and the value I provide, while balancing that with the platform's limitations in terms of showing or burying my profile/ proposals. (In a perfect world, just the first part! Pay me what a nearly 20-year veteran of brand boosting "should" be getting!)
Before Upwork I was strictly project-based/ fixed-price.
On Upwork, there's a lot of opportunity for abuse in fixed-price bids, and with feedback held over your head as a threat, it's harder to put your foot down and say, "you have what we agreed to—project is complete." So I've done almost a 180° on UW—most proposals I send are to hourly jobs.
(Also see previous question)
Hourly—because clients in my line of work often want to add things in as we go, or explore other options, and fixed-price leads to abuses. With a very tight project definition I'll do fixed-price... but I almost always end up with regrets.
1. Catalog Projects
I haven't had takers. Lot of effort to set up well.
2. Boosted Profiles
I've done it. Haven't seen it yield results, no matter the metric. (Do I sound negative about Upwork right now?)
3. Boosted Proposals
It does help to get views and contacts. (Sometimes. Definitely no guarantee.)
Not 100% sure, but I don't think boosting has ever turned into a contract for me, meaning no real ROI—who cares about paying more for increased views, if the views don't turn into jobs?
So with no ROI, I rarely do it anymore.
4. Portfolio
I've got stuff on my profile, but I rely on the marketer's saying that consumers are busy (and sometimes lazy!). I send everything I really want a prospective client to see, as an attachment with my proposal. Rave reviews from on and off UW... portfolio pieces... everything. Show that you value the prospective client's time. Make it easy so they don't have to click around, and you can hold their interest longer.
5. Upwork Enterprise
BLAH. The stuff that gets sent to me from Upwork's supposed talent-matching experts might as well be sent by 100 monkeys trying to write Shakespeare, for all the "matching" to Enterprise clients that I've seen. Never gotten a darned thing that way.
6. Expert Vetted and Top Rated (regular and Plus) Status
I got invited to become Expert Vetted, some time after UW had become a near-total waste of time. It sounded like another way to waste my time. Something to make me feel "engaged" with the site and "chosen" or something. I already know how to feel chosen-or-something, and my engagement is doing me very little good... So I didn't.
Top Rated probably helps... although I can't be in two places at once, so I'm not totally sure. But with how saturated UW is at the entry-level or below, it certainly doesn't hurt.
7. Job Success Score
Again, I can't be in two places at once, so I'm not sure how much it helps. But I can say that when just one client, in my years on UW, gave me a less than perfect score, "because no one should think they're perfect" according to that client, it offended me in a visceral way. So it messed with my heart, if not my views...
8. Any other?
The Upwork forums!
I met great people there. I never got very well known there. I vented there. I sympathized there. I got help there. I gave help there. I shared stats there. I shared knowledge there. (I got irritated by the repetition there...)
Sometimes I checked in daily, sometimes not for a month or two. I did appreciate the forums appropriately? or I didn't appreciate the forums enough? I don't know which. But I certainly thought, as a point of entry into deeper understanding of UW and the world of freelancing/ self-employment, they were critical to the smooth running of the site. And I think it was a stupid, shortsighted move to close the forums down.
Without that dumb move we wouldn't have this site—so there's an upside!
If any, it's mostly the usual client issues, no different than working with clients off-site—like wanting more than was agreed to, making you feel you should add X or Y just to get the work over with even though it's not in the budget, etc. Minor things that calm communication takes care of.
The one REALLY significant client problem I had on UW, was with a U.S. government agency who hired me for a relatively small project that ballooned and ballooned, with endless revisions and COMPLETE changes to the project scope, over weeks—ending when a new contact, supposedly the boss of the person I had been dealing with, suddenly showed up when we had weeks to go before the work would be done, saying that it was required to have been done by [a date in the past!], and that therefore *I* had bungled it and they would refuse to pay me for my last week of work. Then that new person disputed the TWO weeks of pay before that, even though I had months of documentation showing the outrageous situation and how carefully I had communicated and delivered at every crazy turn—and Upwork sided with the client and gave back the money.
All told I lost over $3,000 on it... and all my respect for UW's dispute "resolution" process.
Reskilling, Upskilling & Business Management
There's always a new piece of software that clients think their professionals should be using. (Whether truly necessary or not!) I keep up on features in the ones I'm proficient in, and add in new software learning about once a year. Not massive upskilling, but keeping fresh and on top of potential client needs.
As far as resources: Some software is fairly easy to noodle your way through, just making up a fake project and seeing if you can complete it, because it builds on other software that's already known... some might be familiar but have so many new or superior features that it's not easy to know what you're missing, and of course some are totally new ways of looking at things.
For difficult or unfamiliar software, I start with YouTube where there are always lots of comparison videos and intro tutorials, then I may look for something specialized on the web, or go check out Skillshare. I really enjoy how much further (some) Skillshare teachers take students than YouTubers, from super-beginner all the way up. (Not sponsored, haha!)
Reading. So much reading. Magazines, books, newspapers, blogs, websites, Quora answers, LinkedIn articles... everything. In order to help clients know where their customers' heads are at, and to know where the best design, marketing, and brand growth ideas are coming from, I have to be a research hound, both during and in between client projects. Which I love doing.
I struggled with this question. Brand identity development is a big umbrella requiring a deep connection with a lot of things that fall within its scope. Even looking around at my bookshelves, I can't seem to spot a "branding" book I feel is essential to someone working in this field.
And I'm not sure you can just pop out of nowhere one day and announce: I'm in branding. It's an expert-level discipline that involves having come *from* somewhere: copywriting, graphic design, market research, advertising... and then bringing all those realms together to form your brand development offerings.
So I recommend you read (and watch) everything. Especially in books and magazines, where you can read deep dives, but there's lots online as well. As much as you can on topics like:
- Consumer behavior; how humans make decisions; how great companies found their focus; how to pivot
- Market research; targeting a market; testing market waters; market disruption & innovation
- User experience; user testing
- Brand story telling; shaping/ outlining a story and storytelling in general
- Brand naming
- Copywriting; advertising; pitching
- Making design decisions that resonate; history of graphic design; specific designers you feel a connection to, especially from the past so you can train your eye to see what's dated, what's retro (not the same!), and what's timeless
- World & local politics; behavior trends; technology breakthroughs... and as many specific business areas as you can absorb
Become a nonfiction sponge, because ALL of these things go into distilling a company's essence—so they can talk straight to their ideal customer in the most helpful and compelling way possible.
Hm. Two things, mainly:
- Careful scheduling. ALWAYS give a project more time than you think it will need, both because it *will* take more time than you think, and because *life happens* and you'll need to put little pauses in at some point, for something that just came up.
- Careful siloing. When I'm in work mode, I'm not thinking about personal life things, and when I'm in personal mode, I do not let work things in. The last thing your family needs is to have half your attention. That is also the last thing your client needs—so give them both what they need! I am a professional person, and as such I have business hours. I am not available 24 hours a day and I am not available on weekends. Without limits like that, you're devaluing yourself.
(Now, if you ask me privately, am I ever working on a quiet Saturday afternoon to catch up on something I didn't quite finish on Friday, when I had to take my dad's dog to the vet? I might admit to it... but I do NOT schedule it that way, and I don't allow client bullying about my business hours, no matter what.)
"On the outside," I had a standard contract for working with clients. Within Upwork, I've just made that a lot softer-edged, and I include it in Upwork messages.
I find that Upwork clients are often plenty intimidated by the platform itself. Making something they already find formal, even more formal (and scary) just doesn't have any advantages.
So I make sure we've completely clarified what will and won't be included in the project, and I reiterate everything one more time in a nice clean list and say, "Let's make sure I've got this complete and correct" or something like that. When I have their "Yes, good to go" response, then I accept the job and we're off.
Invoicing: On Upwork, nothing more formal than using notes with each daily logging of hours or with each milestone, and copying that into Upwork messages as well so it's all in one place.
Where You Are Now & Looking Ahead
This self-employed life is HARD. Selling yourself all the time is HARD. Being the CEO of You, Inc.—and the chief sales strategist, chief data visualizer, chief growth guru, chief of every stinkin' department—is HARD. It's humbling. It's risky. It's grinding.
& the more you want it to work, the more you want to succeed—the harder it is.
I don't think I really know how not to be entrepreneurial, though... so I don't have much of a choice. Most of the time, I LOVE this hard path. That's the biggest lesson—that whenever I get away from it, I always come back to it. Because it's how I'm wired.
Having said that... if you're thinking about it, check yourself. Do you have the entrepreneurial gene? If you don't—believe me, there are easier ways to make a buck. O.O
If possible, I'd like to work on more whole-brand identity jobs—from focus to naming to graphic identity and messaging, and move away from one-piece-at-a-time jobs. For startups who have a problem they're ready to solve, and want to reach their ideal customer in the best and most effective way.
Although—in terms of one piece that I'd like to do more of: Pitch decks. When done right, they *are* that combination of focus and messaging and visuals that I love, but on a smaller scale.
Only one?
Start on Upwork way earlier (elance, odesk). Start on LinkedIn way earlier. Yes, owning your own platform means nobody can pull the rug out from under you, but first mover/ early adopter advantage on larger platforms is real, and almost insurmountable—don't worry so much about stretching yourself too thin by promoting your work on your sites *and* on larger sites!
Thoughts: I don't think success is guaranteed to be yours if you work for it. Luck plays a part in every success story. I can't stand motivational garbage about "believe and you can achieve," because it implies that people who don't achieve, didn't believe hard enough. Hogwash! Everybody wants to succeed in some way!
But I do think we each have a right to our own vision and to TRY to pursue it. Whether we get there or not, we're more *our authentic selves* for having tried—and we know we wrote our own story!
So my tagline, from earliest days, has been "Go where your VisionPoints". It's hard to imagine there's any freelancer using Upwork, who isn't trying in some way to do just that. :-)
(This graphic is one of the "goodies" I attach to some of my proposals.)
