Time or money: the freelancer’s dilemma


by Katy Tynan

It’s midnight, it’s raining, and I’m banging my head on my desk. I’ve been staring at PowerPoint, fiddling with colors, and trolling stock photo sites for hours. Worse, I just looked back at the first draft of this marketing piece I’ve been working on, and I swear it looks better than my current version. I’ve spent more than 14 hours today working on this one piece of collateral – an amount of time that would convert to nearly $3000 at my standard consulting rate – and it doesn’t change the fact that this piece still sucks. I know this is not a good use of time. The problem is that time is all I have right now; time, and not money. If I had the spare cash, I could hire someone to do this faster, better, and more efficiently.

As a free agent I almost always have time or money, but rarely both.

The problem is, I’m trying to create this marketing piece for myself to grow my own business. If this were a client project on a client’s budget, I would have asked an intern to do it and it would probably take him no more than a couple hours. If I asked that same intern to do what I do, to present a technology strategy analysis to the board, he would not know where to begin, yet here I sit, fully qualified to do the latter and totally incompetent at what I’m working on now.

I need this marketing piece. I need to put it in front of fifty or more HR decision makers so I can sell seats in a new manager boot camp. I need it to be compelling enough to convince my buyers that this program is not only money well spent, but business-critical spending that can’t be delayed. I need it because I’m in the middle of a dry spell, and if I don’t get some revenue-generating gigs on the calendar, I’m going to be in a tough spot.

So I go back to staring at the screen. All these stock photos of smiling people in classrooms has started to make me nauseous. What I’ve written so far is so insipid it’s destined for the recycle bin. It’s not compelling copy. It’s not a visual masterpiece. It’s not what I need to move my business forward.

Working for yourself means wearing lots of hats. There isn’t an entrepreneur or freelancer in the world who would tell you that they get to focus on the thing they most want to do, or even the thing they do best, all day every day. In fact, one of the great things about the rise of coworking is that it has allowed independent professionals to easily find people who can take some of those other tasks off our plates so we can focus more on the things we do best.

It’s not that I don’t know people who could do this better, faster, and without the head-banging-on-desk frustration factor. It’s that I don’t have the cash on hand right now to pay them.

Cash flow, or lack thereof, is one of the most persistent and pervasive concerns of people who work for themselves. When you have work, you run like mad to get it all done and you stash cash in the bank like a chipmunk hoarding acorns ahead of the apocalypse.

When you don’t have work, you have to make tough decisions about where and when you should spend your time and money.

As a free agent, you often find yourself getting up close and personal with the very nature of uncertainty. If I had a crystal ball and knew that by paying $500 to get this piece done right, the whole project would end up a smashing success, I’d spend the money in a heartbeat.

When I first got started working for myself, I bought a lot of stuff from well-intentioned people who promised me I would make my money back and then some. I bought website design services and PR services. I bought a branding package with really awesome business cards. I invested in business coaching. And while I got great service, I spent more than I had and I ended up short. Would I eventually make that money back over time in my business? Probably, but there’s no guarantee. So these days if I don’t have the money in the bank, I don’t spend it on the hope of future returns.

This leaves me doing things in my business that I just suck at sometimes. It leaves me feeling frustrated when I see my competition putting out kick-ass materials while mine look like what they are—something I threw together at midnight because I just couldn’t stand to write one more word.

While free agents almost universally report that they are happier working for themselves than for an employer, the biggest frustrations remain the same: the challenge of finding clients is number one, closely followed by the feast-or-famine nature of work.

With these floods and droughts comes the need for caution, even when times are good. The need to stretch every dollar often brings about the very thing that will end your career as a freelancer—when you start to worry so much about money and where you’re going to get your next gig that you lose sight of the value you provide. You start to take the wrong work or spend 14 hours on something you’re really bad at instead of spending those same hours finding people who really need your help and are willing to pay for it. You start down a path of anxiety and doubt that often leads people right back to wanting a traditional job again.

We all do it. I do it, and I am supposed to be the expert. I do it because I was taught by school and society that I’m supposed to have a job. A real job, like a normal person. I’ve been taught that working for myself is risky and that there’s no safety net. So when I struggle finding clients or I worry whether my bank account has enough in it to absorb a dry spell, I start to question why I do this work and why I don’t just quit and go back to being an employee.

But then I remember why I don’t do that. I remember that there is no real security in a job either, and worse, there are limitations that aren’t acceptable to me. I lose control over my schedule. I lose the ability to try new things and work on projects I choose. And worst of all I lose the joy of the wins.

Tonight is not a win. Tonight I’m giving up and going to bed. In the morning I will probably dip into my bank account and hire someone to make me an amazing marketing piece. But tomorrow I might also find a new client or do a really great piece of work for the client that I have. Tomorrow I might form a new partnership and find a brand new source of leads.

That’s the other side of the coin that keeps many of us here despite how hard the tough moments are. Because the flip side is that I get to be there when my son gets off the bus most days. I get to do some really amazing work for clients that really need it. And I get to own the fact that I did the hard stuff. So no, I didn’t enjoy today. And I probably won’t enjoy hiring someone to do this job for me, because it’s hard spending money I don’t know whether I’ll get back. But I will enjoy the upsides, and for me, that’s what makes it worth the struggle.

Photo credit: Photo in the creative commons via Flickr user Ant Smith.


  1. Ruth E. Thaler-Carter 05/07/2015 at 12:54 pm #

    There are ways to head off such moments. One is, of course, to at least try to set money aside consistently as a savings cushion as you go along, so there is something in hand to pay for a service that we usually provide to clients. The other is build up a network of colleagues with whom to barter services when cash is tight but something like a marketing brochure, or even an entire marketing campaign, is urgently needed right this minute. And yet another is to remember to market one’s freelance business all the way, even when in the midst of big projects or sweating to meet a major deadline. The goal is a regular flow of income and as few of those traditional freelancer’s feast-or-famine cycles as possible.


    • Katy 06/12/2015 at 3:19 pm #

      I totally agree Ruth – it’s so important to keep a constant flow of sales/business development activities, even when you have plenty of work. Your recommendations are exactly right and I think that’s what a lot of people who are new to freelancing forget to do.


  2. Job at home 06/02/2015 at 7:26 pm #

    Gosh, this speaks to me on a spiritual level, especially those last words of encouragement. Sometimes I get really insecure and worried about whether or not freelancing is the right choice and this article is something I really needed to read right now! Thank you!


    • Katy 06/12/2015 at 3:17 pm #

      I’m so glad the article spoke to you – I think it’s something we all struggle with at times, but there’s not always someone around to remind you that it’s (usually) a temporary thing, and that better times are around the corner!


Leave a Reply