9 Keys to Remote Freelancing

Image by Rebecca Hoover

A highly practical guide based on real-life experience

Last week I posted “The 4 Hurdles of Remote Freelancing.” Because the article was about freelancing, not employment, I feared it might flop.

I was wrong. The magnitude of the response stunned me as readers from all over the world tuned in. It was like the topic hit a vein. What was pitched as an article on the hurdles of remote freelancing, instead seemed to propel the movement forward!

Out of that response, I decided to write a more thoughtful and complete guide to remote freelancing. The tips are from my own real-life experience as a freelance CFO. I’ve also included an excellent point or two from readers of last week’s article.

The tips are loosely arranged in the order you’ll need them on your freelance journey. Please remember, these are simply practical ideas that worked for me. You’ll need to adapt them to fit your unique situation.

9 Keys to Remote Freelancing

Key #1 — Offer an outstanding solution (remote) clients actually need

Let’s start with the “actually need” part. Just because you are a great typist, doesn’t mean clients need typists. Just because you’re a great mechanic, doesn’t mean mechanic shops are looking for remote workers.

Copy writing, finance and coding are popular examples of services remote clients actually need AND are willing to pay for. Any successful offering must meet both criteria.

The second part of this key is an “outstanding solution”. I hate to say it, but if you don’t have something outstanding to offer, you probably won’t make it. The freelance landscape is already littered with mediocrity.

There are basically two kinds of companies looking for remote freelancers:

  1. Those looking for cheap labor to do routine tasks more cost effectively.
  2. Those looking for outstanding solutions not immediately available in their local neighborhood.

You absolutely want to work with the second group which means being able to deliver outstanding results.

I am not saying you need 10 or 20 years of experience. Experience helps, but in the end, competence, speed, reliability and problem-solving-ability matter more. I would hire a CPA with 5 years of experience and those four characteristics, over a mediocre one with 20 years.

In creative fields like copy writing, I don’t think you need experience at all. You just need to know how to write compelling copy. It’s pretty simple.

Key #2 — Know your platform options

The world is not going to beat a path to your door just because you want to freelance. In fact, you probably won’t get in even if you go to their door!

Enter freelance websites. Unlike companies posting jobs on Indeed or craiglist, clients that post jobs on freelance platforms are by default open to the remote freelance model. Popular freelance platforms include Upwork, Toptal, Graphite and Fiverr, to name a few.

My personal journey has been through Upwork and lately, Toptal. Both are reputable companies, but they take an entirely different approach and are the extremes on either end of the spectrum. Here’s my quick analysis of the two:

Upwork. Upwork is a large, freewheeling online marketplace. After setting up a profile, you are free to submit bids on jobs posted on the platform. If a client likes your bid, they’ll usually reach out to request a phone or video interview. If you get hired by a client, Upwork’s fee is generally 10% of your earnings, but it ranges from 5% to 20%.

To make it on Upwork, you’ll need to spend dozens, maybe even hundreds of hours crafting proposals and looking for work, often without much success. I’d say it took me almost 6 months to gain any traction at all. Yet when the traction began, it kept gaining steam like a freight train leaving the yard.

Upwork has a lot of upside if you stick it out. I like the fixed fee contract option. I also like being allowed to have employees (at least on fixed fee engagements). Plus, the low barriers to entry scare away some of the elite professionals and large firms, which leaves quite a bit of open road for caring freelancers who stick it out.

Toptal. Toptal is completely the opposite. Only experienced professionals are allowed to join and there is an extensive screening process. Once in, Toptal does well at making you feel like part of a team.

For example, there are opportunities for personal development. I got my start in blogging by writing for their finance blog. In certain high-demand fields, Toptal offers sign-on bonuses to new recruits and even pays commissions to team members (such as me!) for recruiting. On that note, feel free to apply at toptal.com!

At Toptal, freelancers set their own hourly rate and get paid that rate by Toptal. You have to be sensitive to the market when choosing a rate, but rates do tend to be on the upper end. Toptal recruiters match clients with freelancers and handle all fee discussions and invoicing. For certain fields (such as coding, and certain finance disciplines) Toptal can be a good option for experienced professionals.

Other online platforms. I don’t know much about the other platforms but my impression of Graphite is they lean toward Toptal, while Fiverr is maybe on the Upwork side of the scale, or beyond. I know there are also specialty freelance sites for certain fields (e.g. 99Designs for web designers). Perhaps there are readers with other recommendations?

What about local? I started as a local freelancer serving the central Wisconsin market. Local clients might be marginally easier to find than remote clients, but that depends on your location and occupation. If you enjoy commuting to local clients and working onsite, this could be a good option.

Weigh the options and choose the platform that fits best. You might even try a mixture of options and then quickly latch on to the 1 or 2 that work for you.

Key #3 — Learn to write great, short, introductory proposals

Writing is foundational to remote freelancing. Almost without exception, your first contact with any client will be in writing. In fact, if you can’t put together an effective introductory proposal, I fear for your freelancing career.

I’ve learned a lot about proposals from freelancer Danny Marguiles, who has a business devoted to helping freelancers succeed on Upwork. He is a copy writer himself and has put together some great guides for effective proposals.

Here are some practical ideas I’ve learned myself or from Danny:

  1. Do not waste time explaining all the great things you can do.
  2. Take interest in the client. Offer a suggestion, based on your experience, that works well for what they’re trying to do.
  3. Don’t be afraid to challenge the client. I recently wrote a proposal for a client needing help with a financial model. Their listed budget was $100. In my introductory proposal, I suggested that any freelancer who would actually do the job for that price, might actually take the project backward (emphasis added). I got hired.
  4. If your bid rate is high, humbly explain why. Somehow you need to get past price objections. I’ve found it effective to ask the client if they are looking for results, or simply the lowest cost. That gets them thinking about what they really need.
  5. Mirror the client’s job posting. If the client’s posting has only two lines, they probably aren’t looking for a 2-page introductory proposal. However, when I see a highly-detailed job posting, I’ll respond with a more detailed proposal (and mention that’s why it’s more detailed). Look for specific words or facts in the client’s job posting and use those words in your proposal as much as possible.

Writing introductory proposals takes time to master. You need to find your “voice” and that may not happen in your first 10 tries. Be patient and learn!

Key #4 — Focus only on getting in the door

I think this may be another point I learned from Danny. When a potential client finally responds to an introductory proposal, calm down and remember this: you aren’t trying to sell a project…you’re trying to get in the door. You simply want to be invited into their virtual living room.

The client doesn’t know you or trust you. You don’t know or trust the client. If you and the client are both reputable, you would both be willing to work together — if you could establish that trust. You both need a way to get acquainted so you can decide if you want to work together on the big project.

How do you get in the door to establish that trust? Here are some suggestions:

  1. Offer several suggested times and dates for an interview. Also, convert the times to the client’s time zone. You need to give the potential client an “easy button”. Tell them to suggest a time that works if none of your suggestions suit.
  2. Build confidence by asking questions and giving honest answers. This point is particularly important when you get to the phone interview stage. Ask a lot of (good) questions. Questions give you time to think (while the client responds) and often unearth important facts. When the client asks you questions, strive to be completely transparent and honest. Focus on what you’re good at, but don’t be afraid to admit there are areas of the project you need to think about a little.
  3. Invest time in several conversations or emails. Some practitioners might debate me on this, but sometimes it works. I did a project last year that required a number of free phone conversations to get off the ground. Those talks converted into a low-cost “in” project (see next point) and eventually a months-long engagement that generated nearly $20,000 in revenue. Important caveat: I could also give you plenty of stories that didn’t turn out like that!
  4. Craft a low-cost “in” service. Nearly all my successful engagements began with a small project (for me, it’s often a chart of accounts reboot). I help clients clean up their chart of accounts and if we work well together, that sets the stage for future monthly financial oversight, which is what pays the bills. That is an example from the accounting field…adapt the idea to yours.

As a reader pointed out last week, once a client trusts you to do great work, that client will generally stick with you for a long time. I totally agree, but first you have to get in the door!

Key #5 — Master the art of landing the big project

There are several reasons large projects are important to freelancing survival:

  1. They absorb less client acquisition time. Compare the effort to land 24 projects that pay $1,000 each ($24,000 total) vs. one recurring project that pays $1,000 per month for 24 months (also $24,000 total). Landing 24 separate projects will almost certainly require more effort than landing the one big recurring project.
  2. They generate higher earnings. One large project that takes 4 weeks to complete will generally yield more earnings per week than 4 projects that require 1 week each. That is because the smaller projects will collectively consume more unbillable project management time (aside from the client acquisition time noted in the previous point).
  3. They relieve pressure. Having a large project in hand takes away the feeling of desperation. It also enables confidence when bidding on other projects. This point is so important I think every freelancer should consider lining up at least one large project or gig to survive on before making the leap to full-time freelancing. Your current employer may be a good place to start.

So how do you actually land a big project? Answer: Very carefully.

Here are 11 tips to help you craft a successful large-project proposal:

  1. Provide options. For example, a freelance CFO might offer three levels of service: A) full-scale CFO services, B) month end financial statement preparation only, or C) a bare-bones 4-hour monthly review of client-prepared financials. Ideally, the option you think the client will take should be in the middle of the list.
  2. On your proposal, divide each option or milestone into 3 to 5 sub-tasks. If you simply say “I’ll migrate your QuickBooks file to Sage 300 for $8,000” the client is likely to recoil. However, if you break the task into 3–5 categories (data backup of old system, chart of accounts setup in new system, migration of vendors/customers, set up of new reports, etc.) it suddenly becomes more understandable why it’s an $8,000 project. However, don’t go overboard. Too much detail is overwhelming to the average client.
  3. Give a wide, but reasonable, range of hours. Beside each sub-task list a range of hours. Part of the “getting in the door” phase (Key #4) is having the opportunity to get a sense for how many hours the big project will take. Even then, you never can be totally sure. Make an honest guess and put it in the form of a reasonable range (e.g. 15–25 hours, not 5–100 hours). Add up the ranges to give a project-wide summary range at the end.
  4. Explain specific variables that could impact the hours range. By highlighting specific areas of uncertainty, you demonstrate your expertise and help the client understand the “why” behind the ranges. Caveat: Do not let your disclaimers give the proposal a negative or uncertain tone. Keep an upbeat, fast-paced style, and simply list the variables as key side comments.
  5. Highlight ways the client could help reduce project costs. Clients are entrepreneurial and may be looking for ways their team could lower the cost of the project. Be open to that, and even offer ways to achieve it.
  6. Be clear on commitment/deliverables you will need from the client. This adds credibility and authenticity to a proposal. Deep down, clients know that a freelancer who fails to be clear about what the client needs to do, is probably a short-sighted freelancer. As part of this point, make sure you clearly denote the parts of the project your proposal does not cover. Clarity builds confidence and reduces the chance for misunderstandings later on.
  7. Suggest improvements to the client’s plan. Danny Marguiles mentioned once that clients often “don’t know what they want”. In my experience, he is right. If you can help the client find the best path, it will go a long way to sealing the deal. Caveat: Typically it is not wise to suggest sweeping changes (e.g. changing accounting software). Sweeping changes tend to knock the client out of their comfort zone, which is not a good thing.
  8. Instead of saying how great you are, give relevant examples of past work. No one likes to hear self-praise, but clients do like to hear about past projects. Pack your proposal with examples. Say something like “I helped a contractor on the West Coast migrate from Xero to QuickBooks Online.” A comment like that shows the client you have experience: A) working remotely, B) working with contractors, and C) working with accounting software. That is much more powerful than saying “I am a highly talented accountant and an expert in accounting software migrations.”
  9. If it is a multi-milestone project, provide opt-out opportunities at each milestone. This provision protects both of you, and also saves the client from having to commit the full $10,000 right away. They can take comfort they’ll only be out $2,000 if Phase 1 doesn’t go well.
  10. Tell the client right in the proposal that you might be expensive from a cost standpoint, but not from a results standpoint. If you are a premium freelancer, 90% of the battle is to avert the client’s eyes from their pocketbook to the results. I am amazed how many clients simply cannot connect the dots that a $150/hour freelancer may be able to do a better job in 10 hours than a $15/hour freelancer could do in 100 hours. Likely if you’ve “gotten in the door” you’ve already laid the groundwork for this discussion, but now is the time to drive the point further home.
  11. Summarize the financial components of your proposal on one page and include it as an attachment. I’m pretty strong on the one-page concept for just about anything, but particularly for proposals (see separate article on this point). Carefully craft an eye-catching page that summarizes the information you created in Tips 1–3. Tips 4–10 can then be placed in the body of an email to which the one-page proposal is attached.

Now comes the big moment: Hit the “SEND” button.

Don’t be surprised if nothing happens for awhile. In fact, I often send a casual follow up email or text after several days just to check in and see what’s happening. It might take several phone calls and emails until you finally get the green light (or sometimes, the dreaded red light).

What if the client likes the proposal but not the price? That can be an indication the client is not quite “sold” on you or your plan. Rather than just caving and lowering your price, ask the client if there are specific areas of the proposal that seem unreasonable. If you go through the proposal with the client and highlight the logic behind each point, that may be enough to bring things to a “tipping point”.

If price tension still exists, do not discount the whole project. Instead consider lowering the fixed fee or hourly rate on only the first milestone.

I did that recently on a small project. The client questioned my rates and I agreed to 2/3 of my normal rate for the first 3 hours. The client liked that work and has since paid full rates.

Don’t forget Key #5 was entitled “Master the art of landing the big project”. That little word “art” isn’t in there by accident. A famous artist doesn’t paint a masterpiece on the first day of painting. You probably won’t have a master proposal on your first day of freelancing. Be patient and keep learning!

Key #6 — Think like a project manager (because that is what you are).

Freelancing requires two skills that are almost as important as being competent in your trade. One is marketing (which I’ve covered in Keys 3 to 5) and the other is project management.

Project management is a difficult skill to master. Here are a few tips:

  1. Consider a standard weekly meeting. If the client is agreed, send out a recurring weekly calendar invitation to the key decision-makers on the project. Or, set reminders on your own calendar to schedule project update meetings. Effective meetings are almost always scheduled ahead.
  2. Look ahead for bottlenecks and schedule “bottleneck” meetings. Your work is not your work; your work is looking for bottlenecks. What information are you lacking? What key decisions need to be made in the next two weeks? Figure that out and schedule special meetings to discuss. If you wait until you get to the bottlenecks, the project will languish and maybe even die.
  3. Give advance notice of being gone, and ask the client when they’ll be gone. Recently I explained to a client how the average project goes. I said (jokingly) “we’ll get started and then all of sudden just when I need information, you’ll be gone for a week”. His response: “Yes, but I can get you the information before I leave.” It turns out, he was actually planning to leave on a 10-day vacation in just a couple days! I’ve learned the hard way that client and freelancer OOO (Out-of-Office) time has a big impact on project success.
  4. Look for reasons to communicate. You don’t want to be overbearing, but you need to keep in touch. Don’t hunker down and code for 10 days unless you’ve said that’s what you’re going to do. Reach out with thoughtful questions and ideas every day or two. The client has no idea if you’re actually working, and questions that show you’re elbow-deep in the project give the client great comfort. Bottleneck meetings (Tip 2) can be a great way to accomplish this principle.
  5. Incorporate payment requests into project meetings. There is a real art to getting paid. No matter how much you’ve gone over rates and payment schedules up front (and you should!), the first payment request is still a tough moment. To make is smoother, gently remind the client a few days before actually requesting payment. Ideally, when you send the payment request, it is right after a good meeting wherein you’ve worked out kinks in the project, or showed the client some really good stuff. At the end of such a meeting, casually mention you’ll be sending over the next payment request. Do not simply request payment out of the blue, or after a long stretch of no communication.
  6. Above all, feel the weight of nothing happening. A well-run project flows like a moving sidewalk — relentlessly moving on. You need to carry an outsized dread when the moving sidewalk stops. I don’t mean when it stops for a week. I mean when it stops (unintended) for a day or two. A stop usually means you’ve failed to predict bottlenecks or ask about client absences. However the stop happens, the key is to get moving again. Accept an inconvenient conference call, suggest a different path, jump forward to Phase 2…do whatever it takes to keep moving.

Think like a project manager, because as a freelancer, that is what you are!

Key #7 — Take your communication skills up several levels.

This key is a close cousin to project management, but is big enough to be its own point. A good freelancer must be an exceptional communicator.

Here is my view of what great communication looks like:

  1. It’s ultra-fast. Try to respond within minutes, or at worst, within the same working day.
  2. If it’s in writing, the grammar and spelling are pristine. Painfully take time to make it perfect before hitting “Send”.
  3. It’s not just business. Start emails with “Good morning, I hope you are doing well.” Don’t just dive into a 12-cylinder question. This point can be overdone, but a personal touch goes a long way. And — for it to really work — you actually have to care.
  4. It’s done the client’s “way”. Don’t assume your client’s preferred communication channel is email. Ask the client upfront what their “way” of communicating is. A surprising number of clients prefer texting or phone calls, while the average freelancer is probably more geared to email. Good communication is done the client’s way.

As a general point, if you don’t like writing, or are poor at it, I’d suggest taking a writing class. That’s because writing is the connection point to remote freelancing clients.

A freelancer who cannot write well, is like a door-to-door salesperson who isn’t good at meeting people. When a client is waffling between 2 or 3 candidates for a project, I have a feeling they tip toward the best writer of the 3.

Key #8 — Learn the art of getting good feedback.

This could have been the first point in the list, but it wasn’t because you actually have to do a project to earn feedback. In remote freelancing, online feedback is your reputation.

Feedback is truly a Catch-22. You need good feedback to get work, but you need work to get good feedback. That is precisely why it takes so long to get going on a platform like Upwork.

The upside is once you have the feedback, it is in writing for all the world to see.

Good feedback doesn’t happen automatically. First, you have to earn the right to receive it. Second, you have to help the client understand how much the feedback matters before they sit down to give it.

I always ask my clients to provide thoughtful feedback (if I’ve earned it!) that would help other entrepreneurs considering hiring me. Clients connect with that request because they likely relied on feedback when hiring me in the first place. If you don’t explain that though, the client will tend to simply type “Great freelancer!” (or nothing at all) and go on with life.

You can spend hours creating a compelling profile page, but in the end, client feedback is what tips the scale. People write all kinds of self-serving things in their profiles, but external feedback, especially a long list that clearly comes from many different parties, is much more objective and compelling.

Here’s my personal experience. After struggling a long time to land a job on Upwork, I finally found a client from Boston who was willing to hire me for an urgent short project. It was far below my target billing rate, and I had to work until 2am that night (morning) to get it done. But in the end, he gave me my first feedback (something about “the best value for the money he’s ever seen on Upwork”). That review was the stepping stone to future projects and was worth way more than the money.

Key #9 — Learn to thrive.

I enjoy freelancing. There are days I wonder if it’s what I should be doing, but when I think about going to a day job, I just can’t get there mentally. If my family was starving, and a job was the only option to put bread on the table, I would be an employee in a heartbeat. But in the absence of that, I’ll probably always be a freelancer.

But here’s the thing. Freelancing has downsides. Two that come to mind are loneliness and rejection (like when a promising client totally vanishes without a word). Financial uncertainty is another one. These downsides can be powerful enough to sink a freelancer.

If you like freelancing and want to make it long-term, here are a few practical suggestions:

Suggestion 1. Match working conditions to your personality. Do you thrive on the camaraderie of an office environment? If yes, working from home will eventually be a drag. Consider on-site local freelancing or working from a cafe or co-working space. One reader suggested mixing things up by splitting time between home and outside locations.

If, on the other hand, working from home sounds like a dream, here is a tip: Make sure your family understands when it’s okay to interrupt you. Being available to talk to my wife and children is a great part of freelancing, but some days I feel like yelling “GO AWAY! I’M BUSY!” It helps us all if I explain upfront that it will be a busy day and I need to focus.

Besides choice of work location, make sure to take advantage of freelancing perks. For example, I love taking a walk in the middle of the day. Unfortunately I don’t always make time for it. That increases the likelihood of burnout.

Suggestion 2. Learn to handle rejection. I spoke with a man recently who had just been severely criticized by someone he never met. His response: “I learned long ago not to let what people think of me bother me.” He wasn’t bitter about it, and later when the topic came up again, I could sense he totally harbored no ill-will toward the situation.

Oh that I could have more of that spirit! When I get rejected, I let it bother me for days. That hinders my ability to thrive as a freelancer.

Suggestion 3. Think seriously about finances. For most people it isn’t wise to barrel into freelancing without a financial plan. Based on your desired hourly rate and amount of billable work available, can you meet your financial obligations?

I’ve heard a good rule of thumb is to charge double what you would earn as an hourly wage. If you’re job pays $30 per hour, your freelance rate needs to be $60. In my experience, it should be at least that. The higher rate helps make up for unbillable time and also helps cover self-employment taxes (for USA freelancers).

Freelancing can never be risk-free, but being realistic about a financial plan will help reduce stress and pressure. Less stress increases the likelihood you’ll survive long-term as a freelancer.

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