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Compiled and edited by Julie Tereshchuk

 Is This a Good Time to Start Freelancing?

Dear Mentors,

I’ve been thinking about leaving my F/T position to start a freelance career for a while now. It would give me a lot more flexibility in my personal life; and I have a yet to be my own boss. When the pandemic started, I put it on hold. But, as time ticks away, I’m beginning to wonder if I should just take the plunge now. Pandemic or not! What’s your advice? 




Dear Mentee,

First question, what work will you be doing when you’re happily freelancing, vs. work you’ll take to get by as you get started? Get super-clear on that so you can tell everyone, and we won’t be confused by whatever zigs and zags you take in the meantime. The book “Designing Your Life” from the guys at the Stanford is a quick and super-valuable workbook for just this. It appears overly simple at first, but if you actually do the worksheets they are gems.

Figure out your must-haves and won’t-do’s. For example, and FYI, individual health insurance is REALLY hard to find right now. Would you consider having a side hustle for now to keep benefits, or are you all-in on going solo? How soon? Can you go part time or similar to balance those goals? What is the bare minimum you need to earn in year one to survive to year two? What’s your safety net? Freelancer cash flow flux is no joke. The market is both really hot and really cold right now, and it will take you some time to figure things out. I’m a risk-taker by nature, but I’d hang on to a benefits lifeline until at least Q3 if you can manage to do the freelance launch on the side.

Create a low-value assessment you can do in a couple hours and charge a nominal rate (e.g. $500). Consider it a test first date they can afford. Then, knock their socks off!

Build in a money-back guarantee. It seems counter-intuitive, but especially in the first year or so your reputation is WAY more important than your bottom line. Let’s say you failed somehow, to understand the problem or deliver what they expected, and the client asked for money back. You can wave a contract, get paid, and burn a bridge (Austin is a VERY small-town like that) or you can offer to make it right with extra work, and if that fails, you refund them. It’s important to set clear expectations so this never happens, but the comfort of a money-back guarantee will get clients to try you SO much sooner than if they absorbed the risk. FYI, I have always offered this and never had to honor it.

I’ve got some thoughts on new clients, but I will leave that for another time.


Jenny Magic


Dear Mentee,

Because you have a full-time job, start your freelance work on the side. It’ll be stressful at first, but hear me out — we must always remember the basic economic principle of supply and demand. 

When the time comes that you are too overwhelmed by your freelance work that you have no choice but to transition to exclusively freelance, you shed the full-time job. 

Too many people make the mistake of feeling inspired and jumping feet-first, but if there is no demand, it doesn’t matter how much supply you’re offering. 

Let me be clear — working for yourself is literally the BEST, and I have done it for years, but timing and demand are everything. That said, if you’re independently wealthy, go for it right now!


Lani Rosales


Dear Mentee,

It might be an excellent time as many businesses have cut their full-time staff and are limping along with freelance help. Unemployment numbers are at record highs.

But, I strongly suggest that you do your research before you “plunge.”

Please consider the questions below before you leave your steady paycheck. If you haven’t, it might make sense to add a step: Preparing for your freelance career while you are still employed.

  • Have you evaluated your financial risks?
  • Do you have an emergency reserve that will cover your needs if your business doesn’t meet expectations?
  • Have you considered who your new clients will be? Are they actually hiring right now? Do you have connections to them?
  • Have you factored business costs (time and/or money) into your plan? For example: marketing (website, collateral, social media), legal, CPA services.
  • Have you priced health insurance?
  • Have you built a network for referrals? Could you do so while still employed?

I hope the ideas are helpful. Oh, and don’t forget our excellent Freelance Austin meetings and resources.


Sandra Kleinsasser


Dear Mentee,

This pandemic is affecting people and organizations in vastly different ways. The first question to ask is, “Who will be your target audience?” Once you know that, you need to determine if your future clients and prospects are in a group more likely to be negatively impacted by the pandemic, such as the events industry, hospitality, restaurants, and public transportation for example. Or if they are in a group either not affected, like professional services (such as lawyers, accountants, insurance agents) or more positively impacted, such as technology and CPG (consumer packaged goods) industries.

If the former, now is probably not the time to make the switch, or perhaps ask yourself how you could adapt your services to cater to the latter two groups. If your target audience is in one of the latter two groups, now is as good a time as any. 

One more thing to consider: It’s always easier to launch a business or a freelance practice if you have some money in the bank to sustain you for at least the first three months. If that’s not the case for you, consider a target launch date and set a savings goal in the meantime. That’s a way to get yourself off to a good start.


Maura Thomas


Dear Mentee,

The pandemic has been a challenging time for solopreneurs and freelancers. Networking isn’t as easy, and some companies are cutting back. But some of us have had our busiest year in 2020, devoting more time to work and cultivating new clients. You can weigh whether it’s a good time to leave your full-time job by considering these points:

  • Do you have enough sure-fire clients to carry you through the year financially? Three or four good-paying, regular clients (on a retainer contract) might be enough, depending on how well they pay. 
  • Do you have savings to launch your business? Start-up costs may include creating a website, establishing an LLC (assuming you choose that route), printing business cards, hiring a lawyer to review your contracts, buying professional liability coverage, professional training, etc. 
  • Can you afford health insurance? This is a biggie as many employers shoulder much of that cost. Don’t consider going without coverage, especially with this pandemic still raging.
  • Do you have a plan for expanding your client base? If a high-paying clients drops out, you will need others to fill in. I’ve noticed job banks are not as robust as they were before the pandemic, in case you’re planning on them for leads.


Mary Ann Roser