How to invest in your future as a solopreneur

Howdy! This is Career Freelancer, doable strategies and actionable insights on self-employment as a sustainable, financially rewarding, and engaging career.

One of my career mantras is: bring it on, before you need it.

Put simply, the best case scenario is to proactively expand your skills and explore new areas of your business when it’s not out of necessity. It’s self-directed career advancement on your timeline.

That’s how you earn job security as a solopreneur by experimenting to see where it makes sense to diversify your offerings and upskill yourself.

Two years into self-employment, when I was mainly focused on freelance writing about marketing, I began pursuing teaching at universities.

I didn’t need the work financially, but was interested in providing support on marketing in a less writing-intensive format. I had really enjoyed teaching clients in my past role at an agency, so I thought why not explore this further.

Over the next few months, I put in the reps, guest lecturing in classes at FIT, NYU, Drexel, and SVA to ensure I enjoyed the classroom dynamic, had the skills to teach on the topic, and to showcase my approach to university admins who hire for these types of engagements.

After “auditioning” several times and having three adjuncts recommend me, I landed the opportunity to be an adjunct instructor at NYU. And I’m so glad I did it before I needed it.

All these years later, teaching has become a core part of my portfolio career as a standalone source of income, attracting business opportunities, enhancing my credibility as a practitioner, expanding my skill set, and is an enjoyable, fulfilling aspect of my job.

Expanding into teaching required a significant amount of time, effort, intention, and networking, all of which was time away from paid work. But over the long-term, teaching has allowed me to take on different kinds of engagements, leading to greater career stability.

But you never fully know what will pan out, and what will end up being a momentary blip on your professional radar. I’ve made plenty of career investments that didn’t lead to much.

Like the time I launched a course on my own that only led to a few enrollments, sigh. Or when I spent days registering as a government contractor on the federal marketplace, only to realize that landing these contracts required a skill set and relationships I didn’t have.

Regardless of some missteps, I found that these investments have nine times out of ten helped me prepare for the next iteration of my practice. Even when an experiment doesn’t pan out, I’ve flexed my skills or learned something of value I can apply to paid work.

When you make these investments in your business before you need them, you have more room to make intentional choices and navigate these experiments with forethought.

That’s when the pressure is lower for these tiny experiments to perform in a certain way, which makes them more enjoyable and less of an end-all, be-all for the profitability of your practice.

Research even shows that entrepreneurs with slack time, room for tasks they’re not required to do, have a greater willingness to explore an idea and are more likely to take greater risks.

Compared to expanding into a new area or filling a skill gap when you’re low on work or in a transitional period, when you’re more likely to rush these decisions due to financial needs.

Do what you need to do and feel zero shame about it. But my fear is that you might move in the wrong direction and make more haphazard decisions in these scenarios.

Here’s how to more intentionally experiment as a solopreneur, so your efforts in diversifying and upskilling are time well spent and prepare you for what’s next.

1. Dedicate up to 10% of your time. - Block time on your calendar for experiments and immersing yourself in new skills. If you’re working 40 hours, 10% is four hours a week where you’re making incremental progress on net new investments in your future. Aim for doable actions each week, whether that’s taking an hour-long class, learning a new tool, or networking.

2. Genuine interest is where you start. - These are above-and-beyond tasks that aren’t likely to make you money right away, so it’s necessary that you’re enjoying this process to a degree. Choose which options you’ll focus on based on where you have real enthusiasm for the challenge, the subject matter, the accolades, the potential financial upside, or whatever else you deem interesting. An actual connection to the work will help keep you motivated in the moments doubt creeps in, and you’re feeling the vulnerability that comes with trying something new.

3. Look before you leap. - Before you decide to go all in on a brand new area for your business, do lite research on what the typical time and resource commitment is for this type of work. You don’t want to get caught in analysis paralysis, but it’s helpful to know what you’re getting into before fully committing. Running a small test might be the first step to get real-time feedback and adjust your approach prior to diving in. For instance, you could publish an article on a topic you’re excited about to gauge interest before investing in a weekly podcast on the subject.

4. The off-switch is your friend. - Discontinue any of these career advancement tasks if they’re no longer interesting or aren’t paying off like you had hoped. Your time is valuable, so don’t be afraid to call it quits on commitments you’ve tried and aren’t working out. Set a timeline with flexible milestones for any of these activities to assess where you’re at and inform whether you’ll explore new ways of making this investment work or whether it’s best to move on completely.

That’s the decision-making process I’ve gone through to prepare for the future when self-employed, and what I’ve explored with other solopreneurs planning their next steps. Whether you’re upskilling or diversifying your services, it’s up to you to make it happen.

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