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Five tips that helped me survive five years of freelancing

Over the past six years, I’ve seen it all. From the I can get a kid on Fiverr to build me a brand strategy to the clients who worship at the altar of the Facebook ad fairy, a mythical being that delivers passive income while they sleep. Straight face: I have a budget of precisely $500. Can you build me a million-dollar business by next month? I’ve witnessed freelancers pitching their brand strategy expertise after skimming free eBooks and binging on Gary V videos, which is akin to performing open-heart surgery after having watched The Discovery Channel.

Regardless of how many millionaires in yoga pants tell you to quit your day job and uproot your life, freelancing isn’t for the faint of heart. It’s perfectly fine to crave the structure and rhythms of a traditional work environment. For 16 years, I cried on Sundays, swiped key cards, and sat in offices and cubicles, and I was content with my life. Sometimes I miss comprehensive dental coverage. You try getting a root canal without COBRA. I remember removing the mask that pumped me full of laughing gas and shouting, $3000 PER TOOTH?

No wonder they got me high.

Somewhere along the line, office life was vilified, the 9-to-5 employee was depicted as someone who got duped by the system, while the freelancer tapping away in Bali or Venice Beach had discovered the secret to living their best life, complete with Tony Robbins videos, crystals, and colonics.

I only left my job because I was working for a narcissistic sociopath who drove my self-esteem into the ground while pocketing the millions I made him. At first, I had planned to take a break with the money I hadn’t saved and then start on the painful path of recruiters and first interviews, but then I got one client and another. Since I didn’t need dental surgery in 2013 I thought consulting might be a viable option.

If only I had a crystal ball that showed me stumbling into a Lyft sobbing the $3000 per-tooth root canal circa 2016. But hindsight is 20/20, and it’s no way to live.

For those who’ve leaped, it’s important to navigate this new terrain of accountants, deductions, legalese, and self-imposed structure with the patience of a Buddhist monk. Before we get into the freelancing guide, I want to give you insight into what I’ve learned over the past six years of going at it alone.

1. Get Right With Your Time and Your Love

Nothing says you’re not my priority than telling a client you can’t manage their request because you have deliverables…for other clients. I’ve seen scenarios where a freelancer would say to a client they couldn’t answer a simple question until the following week. People are entirely too transparent with their workload (I’m so slammed with other client work, can I get back to you on this?).

Let me clue you in on a secret: your client doesn’t care about your other clients or workload. Clients care about their problems, and they hired you for solutions.

I get it. You need to juggle multiple clients because of the uncertainty of deal flow. You need to save for the Sahara. Sometimes your clients ask questions that make you want to scream into pillows — why didn’t this post go viral? Why don’t I have 10 million fans on a $2 budget, etc. — and fielding responses requires a level of education (and patience) that’s exhausting. However, let me be clear about something — the fact that you can’t manage your workflow is your fault, not their problem. Educating your client is par for the course, and since they hired you to be the expert, it’s incumbent on you to take them through that journey and explain the whys and how’s along the way.

Right now, I’ve four active clients, and they barely know that one another exist. That’s how it should be. Want to know how I got to this place? Simple:

Be clear about your work arrangement, hours of allocation, and response time for “fires” in your contract.

I go through the pain and bloodletting during the contract process. Contracts are critical because you’re negotiating the deliverable, IP, warrants, and all that other nonsense, but you’re also stipulating how you’ll work with the client on the day-to-day and their expectations on your time. In all my agreements, I define the hours or days allocated to a project, how we’ll mutually manage overages, and I even have clauses about how I’ll manage fires, normal response times on off-hours, and how

I can be reached in an emergency.

I hired a lawyer to manage my vendor agreement from the onset, and I’ll use a lawyer for 1–2 hours if I’m working off a client’s standard MSA/vendor template, so I’m covered. The Middle Finger Project has incredible resources + adaptable templates created by an attorney who gets the freelance life.

Maintain your agreement (because there is the reality of the slippery slope) but be open to flexibility

This is where the discipline comes in, and I learned this the hard way. There’s a difference between a client emergency and dialing 911. Be faithful to your office hours because breaking them is dangerous and lets the client know they have carte blanche to contact you 24/7. If the situation is not urgent, kindly remind your client of your terms when you’re back online during office hours. Use your best judgment in determining what’s truly vital.

However, if the request is a real five-alarm fire (and I better see the blood and bandages), then manage it if you’re available. Your client will be grateful. Remind them that this is a unique, one-off situation but you’re here if the bottom should fall from beneath their feet.

Manage your time

The hardest part of being a freelancer is establishing your structure amidst a day without guardrails and routine. Establish a routine. Use productivity tools like Timely, Asana, Google Calendar, and Trello. And, more importantly, be honest about what you can manage, because while I understand the need to squirrel away cash, at one point you will face diminishing returns and your performance will suffer, which will affect your performance and future referrals.

I can only take on one “big client” during a 3–6-month time frame, and then I can take on other clients where the workload is no more than 10–15 hours a week. For start-up or non-corporate clients, I usually manage two brand projects simultaneously.

Educate along the way

I spend time explaining my why and using data and best practice examples as proof points. I create screencasts of my deliverables that serve as a director’s commentary on my work. I send my clients podcasts, studies, and research that they’ll find useful. Why? An educated client is your best client and the more information they have, the less likely they are to lean on conjecture and guesswork. – Malaysia Micro Service Marketplace

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2. Right-size your approach

Consulting is not a one-size-fits-all approach. A few years ago, I lamented a client to a friend and peer. I complained about how my startup client wasn’t doing things the right way; they skimped on the essentials of branding and marketing, to which my friend responded that I was doing the equivalent of fitting a square peg in a round hole. She said startups don’t have the time, luxury, or money to do everything according to plan, and I have to rethink my approach and focus on the essentials. Deliver that which is truly essential for a business that’s lean, but agile. This isn’t about a textbook definition of what’s right; instead, it’s about what’s right for this particular client. Being flexible in your approach will save you big.

You’ve probably heard the phrase “the riches are in the niches.” As soon as a term gets popular, I develop an allergy toward it, but there’s a kernel of truth in specialization. While I’m capable in many aspects of marketing, I don’t necessarily like the things I’m good at (i.e., social media marketing, influencer management, etc.) Over the past three years, I’ve worked solely with start-ups to mid-sized companies on brand strategy, development, and messaging. So much so that I’ve got a strong process flow and the expertise in knowing what works and where I can save time and money.

My friend’s advice has remained with me. What I would deliver to a billion dollar electronics giant would be markedly different than my deliverable to a start-up clothing brand. Usually, the latter is leaner, tighter and execution-heavy. Yes, there’s a strategy in both, but the strategy for an established brand or business is demonstrably different than the needs of a burgeoning brand, whose positioning and value proposition may change throughout refining their product or service.

While I mostly work with smaller companies, I’ve learned that I have to adapt my approach by client, size, and industry.

Be prepared to be a consulting chameleon. Assess your client’s objectives, evaluate their resources and budget, and deliver what works best for them now, even if it’s a phased approach. I LOVE a phased approach because it gives me the flexibility to add and refine over time while offering the client a more risk-averse approach (and they can see your BIG THINKING!). All too often I see startup founders shake their head when reviewing a proposal, with a “that’s nice, but that’s not feasible when I’m still trying to get my product in shape.”

In short, be flexible. Be malleable. Realize when you fit square pegs into round holes.

3. Don’t send in a SWAT team to collect payments

No one believes in getting paid on time more than I do. If you expect me to deliver at a specified time, I plan to be compensated for my work at a specified time. However, we live in the real world, not an imaginary one, and sometimes in this world, people in accounts payable go on vacation, people forget to submit your invoice for processing, or the direct deposit might take forever and a day to set up correctly. Give your client the benefit of the doubt and don’t roll in acting as a collection agency if your check is under five days late. Client service was invented for a reason, people.

While I establish late fees in my contract (usually when payment is over 30 days), I also specify and negotiate payment terms in my agreements. I start with a 50% project deposit, payable upon contract execution — the remainder of the payment comes on delivery. For some clients, fees may be cut up into thirds aligning with milestones, but typically get as much cash up front because you never know. Also, in my experience, I’ve found that the larger the client, the longer the payment terms.

I don’t get out of bed for less than N30.

After I invoice my client, I wait for 5–7 days after the payment due date before I send notes of inquiry because I try to exercise the belief that most people have good intentions and want to pay for the work you’ve delivered. And while I’ll send out the troops for clients who are deadbeats (this is rare), don’t issue the brigade if the payment is a few days late, and exercise compassion for when clients have good reasons for delays.

Also, while it’s important to track your project hours, don’t get crazy over every billable hour. I’ve used Timely to understand the typical time I spend on a project. When you’re a freelancer, you’re the accountant, admin, project manager, etc., so tracking time is essential to determine if you’re making money or if you have an expensive hobby. I use the time to assess my project rate (I don’t bill hourly because that penalizes pros) as well as how much I need to make per month to be sustainable. Check out this excellent post from Paul Jarvis on pricing.

But don’t nickel and dime your clients. Scope creep is real, and you should communicate to your client when the project is going off the rails or is veering from your plan. However, if you’ve got a great client who pays on time and they make one occasional small request, honor it. There’s a difference between doing your client a solid and being taken advantage of.

While I have iron-clad agreements and I’m pretty direct when it comes to how, when, where I work, I allow for a degree of flexibility for the times when I know being flexibility is an investment in the relationship and future business. Be smart. Don’t think in the billable moment.

4. Always be prospecting

One of the hardest lessons I’ve had to learn is that you have to be as much invested in your business as in your business. Easier said than done, right? I get it. Who wants to be pitching and networking when you have actual work to do? But guess what?

New business and nurturing your pipeline is part of your job as a creative entrepreneur.

I think of it in terms of planting seeds and tending to your garden. This is all about keeping up with past clients, refreshing your testimonials and case studies, meeting up with peer freelancers over Skype or Zoom (other freelancers are an incredible resource for leads as well as sharing your joys and gripes) and forging non-creepy relationships with people on and off-line.

I’ve made the big mistake of not considering my pipeline when I’m the midst of a bountiful few months, and then I ended up with weeds in my garden and negative integers in your bank account.

Don’t do this. Set aside time each week to focus on growing your business and maintaining leads.

I’ve created education guides (e.g., social media best practices, worksheets for branding exercises, etc.) that I use as investment products and soft sells. Once I’ve established my value with a client, I’ll often send guides that are relevant for their needs/business, with no explicit sell. I’ve done mini-education sessions (or the clients have used these guides for internal education), and I’ve almost always secured more business because of it.

Be strategic about the sale and offer additional services when you’ve established trust and value, and have some back-pocket tools that you can provide that can bring you closer to a deal.

5. Nail down your processes

So. Not. Sexy. Right? I had a near-coronary moment when I tracked my hours and realized just how efficient I was at managing my admin work. I know, time tracking is medieval torture, but how will you know if you’re productive and profitable? I was going by my gut for three years, and that was just stupid.

Not only was I reinventing the wheel every time, but I was also out in the forest chopping wood. There are so many online (and free!) tools that can help you manage everything from your email and schedule to lead generation and file management. Test and see what works for you and implement that technology into your process.

For me, I like to keep things simple. I use Google email and calendar, but my clients use Calendly to schedule appointments, so we don’t waste ten emails sorting out a meeting time. I use a screencast plugin for Chrome to record any voice-overs for deliverables so I save hours on conference calls going through slides. Calls are now about questions and discussion, not deliverable presentation and review. I use Dubsado to track leads and send out contracts, invoices, and automated emails based on dates and specific client actions.

Also, I’ve created a new client magazine. It’s a designed template I purchased off Creative Market, and it gives the client everything they need to know when working with me. It includes all the housekeeping (e.g., W9s, payment options, contact info) to hours of communication and file management. I also have three versions of a client questionnaire, which allows me to learn more about their business and ask for assets so I can get started with my work. I also include a timeline in the document that outlines the deliverables but specific actions they need to take against deliverables and approximately how much of their time is required. Clients love this.

In the end, you want to design a process that pushes progress. Lock down repetitive emails and tasks into an automated system so you can spend time on the actual work and client relationship.

What I love about being a consultant is that there’s never room for complacency. When you think you’ve got something figured out, the thing changes shape and form, and you’re forced to adapt. You have to keep your skills and technology fresh. You have to nurture your relationships in a real way beyond the exchange of virtual business cards and blog post links. You have to work to cultivate a community that will gravitate to your work and vibe and repels those who aren’t getting it.


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