Many young new grads consider the possibility of freelancing/self-employment and skipping the 9-to-5 path altogether. They have an advantage at that stage — they still have roommates and split bills like rent or utilities, maybe they have a car, health insurance, or cell phone still paid for by their parents, and a built-in 6-month deferral of their student loan payments to help support them in this transition.
In other words, they need less and can get going more sustainably with a lot less pressure at the beginning.
But what about those of us who are a little more seasoned?
Those of us with a stable paycheck that currently needs to cover things like:
- Our mortgage/rent
- Children
- Home and car insurance
- Full-swing student loan repayments
- Adult-sized health insurance bills, etc.
And have no one to split them with.
What about us? Are we dead in the water before we even begin?
In this article, I’m talking to the 30-to-50+ somethings about how to make the transition from a full-time career to a full-time self-employed adult. I did it, and you can too.
Let’s dive in.
The Problem with Trying to Pivot in Your 30s+
Pivoting your career toward self-employment at even just a slightly later-in-life stage comes with a few added challenges beyond the bills. You have also:
- Built your career to a certain level in a certain field, and fear having to start over again in the event the self-employment thing doesn’t work out.
- Have no proof you can do it, so you doubt yourself.
- Knowledge that you’ll have to take a pay cut during the transition — a sacrifice you may not want to make.
- A justified discomfort with the idea of irregular income and enjoy your predictable bi-weekly paycheck.
- Difficulty picturing yourself with the amount of audacity you need to try —potentially fearing the vulnerability of putting yourself out there (on your website or social platforms).
- A fear of failing.
And I’ll be honest with you right now, self-employment is not for everyone. Your income will fluctuate, especially at the beginning.
If you struggle with financial management (namely, setting aside income in the good months to stabilize the slow months), for example, it will be much harder for you to make a sustainable career out of your business.
But a lot of those listed fears are in our own heads. For example, will we actually have to start from scratch if our business fails? Or is that business a resume-boosting experience in its own right?
Is proof really something we need to make our dreams happen, or is it just nice to have? Has anyone succeeded without prior proof they could do it? Of course they have. You can absolutely do it too.
How to Get Your Self-Employment Journey Started: Your First Investments
It goes without saying, so I won’t spend much time on this. The very first thing you’ll probably want to do is figure out what business you’re interested in starting. For a low-startup cost business, many of us start with service-based freelancing.
Here’s my article on how to find your freelance business idea if that’s the path you want to take:
Break into Freelancing in 2024: The 4-Step Guide
But every business regardless of the business model/industry needs to consider startup costs — the more you invest in your business the more you have to lose right?
Well, it’s not quite that simple.
Frivolous spending at the beginning can put a chokehold on your business and early cash flow. Things like:
- A brand new DSLR camera to film content
- A snazzy studio to display products or host clients
- Expensive high-end equipment (like a new laptop or top-of-the-line custom packaging)
- Etc.
These investments aren’t always the best choices when you have other tools you can use in their place (like your cell phone camera or standard USPS boxes, for example) to prove your concept and earn your first dollar.
But not every investment is frivolous spending.
Here’s the thing: Where the new grads have a lower cost of living advantage, you too have an advantage: your current stable income.
I’ll show you how I leveraged my full-time desk job to build a more sustainable transition path for myself.
I took some time to prepare for the leap of faith I took. And since I didn’t yet need to live off the income I made from my business, I could keep reinvesting it in that business to start and grow it faster.
So what did I invest in at the beginning and why? Let’s talk about it.
Mentorship/coaching
We older adults have a lot less time than a new grad without a full-time job, so we don’t want to learn everything the hard way — and we thankfully don’t have to.
Mistakes are inevitable, but investing in someone’s time to learn from their experience and/or help you avoid some of the costlier mistakes can pay dividends in the long run.
So I took this path and found people I could ask questions to and hear stories from — it helped me avoid a lot of common mistakes I otherwise absolutely would have made.
Self-Employment Education
If you have $1000 to invest in your new business, I’d recommend 30%-50% of that should go into education before you start.
Why?
For so many reasons.
You don’t know what you don’t know, and learning from someone in your desired field can help you hone in on your idea and make it much more viable than it would have been without that training.
It’s the principle of knowing what to Google being more useful than knowing how to Google.
Education can also give you:
- A competitive edge
- A new skill
- The unfortunate, yet simultaneously very fortunate insight that the business you had in mind is actually one you don’t want to start
- A new idea, angle, or approach for how to start your business
- And more.
I invested in courses and workshops to train me on the concepts I felt would be most valuable to me like SEO, programming, web development, and niche marketing skills.
Professional services
As a seasoned worker, we have a lot more experience to draw from than our new-grad counterparts.
This includes, in large part, direct or indirect exposure to real adult business problems like taxes, lawsuits, HR, risks, and contracts.
New grads without experience are much more optimistic, trusting, and likely to get exposed to these types of problems when they run into them firsthand — a much more expensive way to learn these lessons.
If you have money to invest upfront, you can learn how to save money down the line through things like a strategic business structure, solid contracts, properly tracked expenses, minimized risk exposure, and more.
I invested in time with both legal and accounting professionals to make sure I knew things like:
- That I had the correct business structure
- What pitfalls to avoid to keep my business legit
- What types of investments were expense-able and which would come out of pocket
- Where my potential risk exposure was
- Etc.
A website for your self-employment venture
I know it’s Squarespace’s tagline, but “A website makes it real” couldn’t be more true.
Securing a domain and hosting for your new website can run you a few hundred dollars upfront, (unless you choose a pay-as-you-go platform like Squarespace or Shopify), but this investment creates a virtual business address for your self-employment business and turns it from an idea into a real thing.
A website was one of the first investments I made in my early freelance business.
Templates & software
Finally, it’s important to remember that if you can automate it or buy it from someone, you save yourself time.
Here’s an example — imagine you’re paid $30 an hour for your work (roughly $63K a year). If something costs you $30 to buy, but saves you 4–5 hours of research and work, it’s well worth the investment (consider it a savings of $90–120).
The same goes for things like a CRM (customer relationship management tool) — if you can automate your processes you’ll save yourself a lot of time.
Time = money in a lot of ways, so many of these investments pay for themselves.
I knew my time was my most precious resource, so I wasn’t afraid to invest in preserving some of it.
How to Get Ready for This Self-Employment Transition: What to Do Today
Your job also offers another advantage over starting as a new grad — access to experience. If you’re toying with the idea of starting your own business, here’s how to use that advantage to boost your future.
Get paid to learn
You can learn all about running a business from the business you’re working within. Here’s what you can do before you quit:
- Take on outside-of-the-box projects
- Join meetings for other departments
- Ask questions
- Watch the leaders and decision-making patterns
- Offer to help with accounting, IT, HR, or any other department that you’re less familiar with
- Chat with colleagues
- Ask more questions
- Take ALL the notes you can
Use your job as an opportunity to get paid to learn how to run your own business. Think of every additional task as a learning experience. That’s what I did and I’m thankful for it every single day.
Use your weekends to build your dream life
So many of us use our weekends to escape a life we hate, when we should really be using them to invest in the life we want.
Short-term pain for long-term gain.
I spent my early weekend mornings (coffee time) on courses that prepared me for that eventual leap, knowing mornings were when I had the most energy, free time (no outside obligations), and focus.
I also used my lunch breaks during the week to sit in my car and read articles, listen to podcasts, and learn from those generously offering up their experience in my desired field.
If you don’t have the time, see where you can find it. 10 minutes every day is better than 0 minutes.
Start with one or two minor investments
There’s nothing more defeating than wasting years of your life building a business that you end up disliking just like the job you have today.
Take the time you have (whether it’s on weekends, early mornings, lunch breaks, or after-work time) and start trying your business on for size.
Whether that’s investing in a mentor, a workshop, a course, or legal advice, each dollar spent in this way adds value to your professional skillset. Those often pay off even if your business doesn’t work.
Closing Thoughts: Pivot Your Career
Start reframing your thinking about your current job and age — these are not hindrances to your business, they’re an opportunity to start it better and more sustainably.
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