Freelancing is enjoying a moment as more people leave their full-time jobs to become their own bosses.
In mid-2021, an Upwork survey showed that
1 in 5 professionals was considering moving to the freelance working style. Of those respondents, nearly three-quarters said part of the reason was to enjoy greater scheduling freedom and the opportunity to work remotely.
Certainly, freelancing offers some compelling advantages for anyone fed up with the traditional grind of being an employee. After all, freelancers aren’t beholden to anyone but themselves. They can also fire clients if they want or even leave the office on a whim at 3 p.m. to go for a bike ride.
Plus, companies hard-hit by the Great Resignation are becoming more open to leveraging freelancers to fill workflow gaps. Fiverr’s internal research showed a
44% year-over-year rise in freelance job posts between the first quarters of 2019 and 2020. And during 2020’s second quarter, CNBC reported that
freelance job openings were up by 25% — which was great news for the millions of folks interested in turning their side hustles into front-and-center occupations.
There’s little doubt that these are exciting times for anyone who wants to take the freelance plunge. However, whether you come from Generation X or Generation Z, you need to make the right freelance business investments to ensure efficiency and effectiveness in your endeavors. Otherwise, you might find yourself unable to keep up with the physical and psychological demands of carrying the full weight of being a “solopreneur.”
How do I know so much about this? I made the transition to freelance work decades ago. As my business has grown, I’ve moved to being an employer. Nevertheless, I love hiring freelancers. And I want every freelancer to develop smart habits to set themselves up for success by following a playbook that will lead to better self-management.
Starting off on the right freelancing foot
Why is self-management — and management of everything — necessary as a freelancer? Allow me to illustrate with a tale from a tale. You might have heard of Stephen Covey’s bestselling “The 7 Habits of Highly Effective People.” I recommend you read it if you haven’t yet. Among Covey’s nuggets of wisdom is a story I think about from time to time that translates well to freelancing.
Covey writes of an employee who has succeeded in tracking his time and blocking out what needs to be done to complete all the projects on his plate. When Covey approaches him with an urgent new task, he points out the projects he’s already committed to completing. He then asks about which existing task Covey wants him to drop to address the urgent new item. Nonplussed, Covey realizes that what he thought was urgent wasn’t actually that pressing in the scheme of things. Covey tells him, “Keep doing what you’re doing,” and he finds someone else to help.
When I read that passage the first time, a light went on for me. If a person implements the tools of smart focus and commitment management, why would that person need a boss?
In other words, if you’re going to get all the good stuff that comes with freelancing, you have to set yourself up for success. For instance, let’s say you’re not quite a freelancer yet. You have a 9-to-5 job. But your instincts are leading you toward freelancing. What should you do?
Now, I think everyone who works should have some side business venture, if for no other reason than to realize tax gains from a hobby. However, the secondary value to a side venture is that the more time you spend freelancing, the more valuable you will be as a full-time employee. Remember: You’ll have learned to self-manage and prioritize like nobody’s business. Consequently, when you’re ready to resign, your employer will be more likely to see you as a valuable asset that isn’t worth losing. So you might be able to negotiate some flexibility and stay on a bit longer — all on your terms and within the boundaries you set.
Truly, being a freelancer should change your mindset if you let it. Being responsible for your own profits and losses will help you become better with money. You’ll also start to develop ideas and general business chops. For instance, you might begin to weave sales talk into conversations naturally. You might also pitch concepts to people who were just acquaintances before. Believe me when I say that you’ll know the freelance chance is happening when you begin to view the world as one that’s filled with opportunities.
This doesn’t mean that making a move toward mentally embracing freelancing will be a breeze. Cash flow worries plague freelancers, and particularly those who have become accustomed to receiving a steady salary along with healthcare and other benefits.
When I struck out on my own after college as a piano tuner, my monthly revenue was all over the map. So was my emotional state. Over time, I learned to control both my feelings and my bank account. I found out that what seemed to be a roller coaster of income peaks and valleys wasn’t. Year after year, there was a solid mean that my salary always returned to. I just had to be patient enough to collect and parse the data. With that information in hand, I knew how much I could expect to make, which helped push away worries when business wasn’t as heavy.
The freelancer’s oasis: must-haves for maximum impact
Maybe you’ve gotten yourself into a great headspace for freelancing. Now, it’s time to start making the right freelance business investments in the tools that will make freelancing much simpler. It doesn’t matter what your “craft” is — the right tools can make all the difference.
Below are some of the biggest must-haves and to-do’s that belong at your fingertips as a freelancer. Depending upon your industry, you might discover others, too.
Get financial help or software
Right from the start, either invest in a robust accounting software system or pay an accountant to handle your books. Take this step even if you’re showing no revenue or sales.
According to CB Insights,
38% of startups fall apart because they run out of cash. Technically, your gig could be considered a startup. By getting a grasp on your financial picture right from the get-go, you can avoid falling into the trap of losing steam before you gain momentum.
As a side note, be sure to keep statistical information on your freelance finances. That way, you can better predict seasonality.
Block your schedule for closings
Let’s say you just opened your freelance business. You don’t have any sales or customers. Rather than waiting around, block off your schedule for potential closings and appointments.
Now, when these periods pop up on your calendar, your mind will start to think about ways to fill the empty slots. You might want to do a little hunting on LinkedIn for potential clients or publish content on your social media pages.
The point is that you’ll force yourself to do something simply by blocking off time. It’s akin to telling yourself that you want to buy another car. Suddenly, you start seeing chances to purchase automobiles all over the place. The same phenomenon will happen when you’re freelancing.
Buy decent office furniture
Have you always worked from a well-stocked office? You probably didn’t appreciate how much money went into solid filing cabinets, workstations, and desk chairs.
Resist the urge to go cheap and outfit your home office with stylish yet subpar furnishings from Ikea or Staples. Yes, you’ll pay more, but you’ll more than account for what you pay by not having to go to the chiropractor regularly.
Likewise, great office furniture and lighting don’t just provide good value or
health benefits — they also promote nose-to-grindstone working. For example, a noisy, clunky file cabinet can become a massive deterrent for wanting to file papers or sit in your home office space.
Fill your library with books
You don’t need to have a bookshelf in your work-from-home space. Still, you should have at least a few good books handy. I do. There are specific titles I reread from time to time because they give me encouragement, inspiration, and advice.
The books that resonate with you might be different than the ones that resonate with me. Nevertheless, I suggest having at least some that teach you how to maintain lifetime customers, work with vendors, and market your services.
What are my favorites? The aforementioned “7 Habits of Highly Effective People,” David Allen’s “Getting Things Done,” and “Atomic Habits” by James Clear. “Your Money or Your Life” by Joseph R. Dominguez and Vicki Robin is a runner-up, as it helps you recalculate your financial objectives.
Work with cloud-based systems
One of the best pieces of advice I received after living through the dot-com bust was to move to cloud-based office solutions. Why? Running a server was bound to be ridiculously expensive.
As a new freelancer, the last thing you need is to sink money and time into nursing a stack of physical hardware and custom software. Leave all those hassles to platforms in exchange for a subscription. You’ll stay agile, resilient, and flexible through landscape and market changes. Additionally, your clients won’t know a thing.
Case in point: We’ve changed website hosting platforms multiple times to save time, money, and headaches. But as far as our customers are concerned, we’ve had the same storefront all along.
Sidestepping pitfalls on the road to making freelance business investments
If you’re like many freelancers, you might theoretically agree with my thoughts but remain terrified to make any financial investment. Accordingly, you’re trying to launch a business while seated at an uncomfortable dining room table or using software that just isn’t cutting it.
Rather than allowing obstacles to halt your progress before you make half a step into your freelancing future, follow these strategies that avoid common pitfalls:
1. Rid yourself of a scarcity mindset.
What’s a scarcity mindset? It boils down to thinking you have to do it all. And it will hinder you in finding new business, not to mention lead to jealousy. You’ll convince yourself that there’s limited work available.
Go against the negative voice in your head. Collaborate with other freelancers, including ones working in your field. Stay open to possibilities. Adopt a desire to learn something new every day.
2. Rethink everything.
We all have beliefs that hold us back. One of my mythologies was that success was signaled by a corner office fronted by a highly skilled receptionist or a delightful storefront with lots of attractive accouterments. Fortunately, I’ve challenged these conventional norms.
Don’t be afraid to question the usefulness of something that seems obvious. Some old truisms aren’t true when you take a closer look.
3. Push against the temptation to invest in physical space.
Even if you occasionally require a brick-and-mortar space to hold meetings, think twice about signing a lease. Having a physical location can backfire quickly — and not just moneywise. You might discover that clients aren’t willing to drive to your company because the parking is bad. Or your landlord might be unwilling to fund an asset to make sure you’re compliant with the Americans with Disabilities Act.
You certainly won’t be the only freelancer without a storefront. Just make sure you designate a portion of your home as a dedicated office space to corral the tax benefits and let it go at that, at least for now. Our websites and social media presence are all we need. I rarely even hand out business cards, to be honest. Plus, when a company the size of Salesforce is closing down new skyscrapers, I’m relieved not to have that burden.
Do you have the freelance itch? Instead of assuming that you have to grab some balm, go ahead and scratch it a little. You don’t have to hand in your resignation right away, though. You can still get all the perks that come with freelancing — including a home office tax write-off and perhaps local grants — without losing your steady income. In the meantime, be sure to invest in the tools and strategies that support you. When the time is right, you can take off the training wheels and glide into the exciting world of being the boss.
