Owning the mindset shift of self-employment

Howdy! This is Career Freelancer, insights on embracing freelancing as a sustainable career path, not as a stopgap. These are the doable strategies behind successful self-employment.

The thought of diving into freelancing is quite appealing. The possibility of more freedom, flexibility, and no boss telling you what to do is enticing. But making it work long-term beyond the honeymoon period is more challenging, given it’s primarily up to you to design a lasting career as a self-employed professional. It requires a mindset shift.

The rules and structures of salaried, full-time employment don’t apply, as you’ve got more options to choose from, which can be refreshing and overwhelming all at the same time.

You’ve got to be open to a wider variety of possibilities for structuring your career to take full advantage of the benefits of freelancing and minimize its pitfalls. Plus, letting go of the preconceived notions about what work looks like can provide you with more flexibility and fewer restrictions in the long run.

This can be challenging given there’s fewer guidelines to follow, and changing the way you approach work can be daunting, given there’s no shortage of directions to take.

As a career freelancer of 12+ years, here’s how I’ve learned to rethink what true freelance prosperity means to ensure it’s a sustainable, enjoyable, and rewarding path.

1. Establish your north star statement on freelancing with specifics unique to you.

The best starting place is beginning to find clarity on what you want from your career and how it supports your life in and out of work. A north star in this context is an overarching goal directing how you build and sustain your practice.

You won’t figure this out overnight, but begin by making a list of what you want and what you don’t want from your professional life. The point of the list is to narrow in on what your priorities are and then slowly begin to build your ideal work structure around that.

You might be seeking more creatively fulfilling work, better flexibility to walk your dog in the middle of the day or pick your kids up from school every day, or higher-paying work.

On the other hand, you might want to avoid working on highly technical projects or commuting to an office. There’s no right or wrong answer; it’s figuring out what’s productive, profitable, and enjoyable to you professionally and designing around that.

Defining your north star can be a specific goal or a broader future set of circumstances you’d like your freelancing efforts to get you to. Again, no rules, but to make this tangible, aim for your north star to be a sentence or two to ensure it’s easy to follow and refer back to.

Some examples:

-- My intention is to build a six-figure freelance practice with B Corps and value-driven organizations, while working in a sustainable way, no more than 30-to-40 hours per week.

-- The goal for me is to freelance in the healthcare space to comfortably pay my bills, save for the future, and have the time and space to be with my kids in the mornings and evenings.

-- I want to be a recognized voice in public relations, have a steady flow of challenging clients, and avoid burnout at all costs.

-- Develop a work model for my coaching practice where I’m making $100K a year, able to work while traveling at least once a quarter, and have plenty of room to volunteer weekly.

Naturally, your own north star statement will be unique to you, but recognize it’s not permanent as you’ll adjust it as your work and life evolve. It’s better to have one in place as a reference point to guide you and be open to necessary updates as you go.

One of my north star statements is (you can have as many as you’d like): I want to work four days a week by 40, three days a week by 50, and at that point, I’ll feel basically retired only working three days and being off four days a week. That’s my doable dream.

2. Recognize that the who, what, when, where, why, and how of employment are modifiable.

Whether you’re equipped with a north star statement or still composing one, it’s about finding a direction in freelancing that suits you and taking action to make it a reality.

Who you work with, what you work on, when you work, where you work, why you work, and how you work day-to-day is all guided by your own statement, as every freelancer is unique.

It’s important to recognize that we often think of the who, what, when, where, why, and how of work in terms of the established structures of full-time employment.

Like operating on the assumption that work has to happen from nine AM to five PM Monday through Friday, a full workday is eight hours, or a professional is most productive working with their team in an office environment.

These aren’t universal truths you have to abide by, and you must adjust how you show up as a freelancer based on what makes you happy, productive, and financially sound.

These adjustments could mean only working six hours a day as long as the work gets done, solely supporting clients that support diversity, equity, and inclusion in the workplace, or creating your own framework for handling project management outside of best practices.

Take a step back and assess what facets of your freelance work serve you and where incremental adjustments can be made, as there’s more room for innovation here than you think. It’s an iterative process that happens one step at a time.

And yes, there are definitely realities we can’t ignore as we’re often supporting companies and individuals that operate under these traditional established norms, but you don’t need to (and probably shouldn’t) follow them exactly.

3. Connect with other freelancers for exposure to the range of options.

How do you know what options are available to you in the land of self-employment? Building relationships with other freelancers.

It’s one of the best ways of expanding your mind and exploring new pathways, so you’re taking full advantage of the benefits of this arrangement.

Not in a transactional way, but finding friends and colleagues you can support and are open to providing advice and guidance on what’s worked for them along the way.

Whether they’re just starting out as a freelancer, coming back to freelancing after a recent windfall of success, they’re a direct peer, or they’re way ahead of you, it’s worthwhile to meet and befriend a mix of independent professionals.

There is no shortage of lessons to learn from folks at every stage of their development, as the options available aren’t reserved for well-seasoned colleagues alone.

Over a monthly coffee or occasional Zoom call, make the time to see how others are building and structuring their freelance practices as a source of inspiration for your own.

4. Give yourself time to adjust to new circumstances and pivot as you go.

Change is hard and all that, so be patient with yourself. Much of what we’ve been taught about work is deeply ingrained in us culturally, economically, and socially.

You’ll have feelings of guilt, uncertainty, and anxiety at times as you start to make shifts that contradict standard practices.

As I’ve freelanced now for over a decade, I feel a deeper sense of clarity every year about what I want from my business and life. This makes what I’m working towards clearer in some ways, and sometimes the outcomes I’m considering change significantly.

My advice is to remove the pressure of getting it perfectly right and take small, daily steps towards creating a freelance practice that makes sense for you. We’re all figuring it out as we go, and you will too.

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