Last month I announced on LinkedIn that I was making a career move. Instead of applying to full-time software developer positions, I was going to take my employment into my own hands as a freelancer. This decision comes on the heels of nearly six months of research and reflection about the right next step for me. Before I get too far into this process, I want to capture my initial hopes and ambitions, so that later I can compare them to my new reality. That seemed like as good a topic as any for a first blog post.
Understanding the system
I have a lot of opinions about the way I believe business should be conducted. Many of those opinions conflict with what I’ve observed from the corporate world after almost a decade as an adult consumer and full-time employee. Some examples of practices I object to include:
- Emphasis on perpetual, exponential growth at all costs.
- Withholding information to manipulate employees. For example, sugar-coating the company’s financial situation to avoid attrition.
- One-way double standards of loyalty. Relying on two weeks’ notice from employees out of their goodwill towards coworkers, then denying long-time employees so much as a Zoom farewell before laying them off to cut costs.
- Divides between the inner circles of executives, middle managers, and associates that result in zero-trust attitudes and policies.
- Long-term negative consequences, endured almost exclusively by associates and managers, due to the decisions of C-suite executives who have long-since left the company after pocketing millions in “incentives”.
- Disconnects between company goal-setting processes and the actual nature of the work to be done.
- The rinse-repeat Silicon Valley tale of the “industry-disrupting” startup founders who abandon their ideals and sell off their brainchild to the very players who control the industry they were disrupting.
I feel justified in my frustrations. And yet, I also feel underqualified to criticize these practices, because I’ve only been on one side of the aisle. One memory from my last company stands out.
Following a major layoff, I wrote and published an internal memo criticizing the way the layoffs were handled. This was received poorly by engineering leadership, but not for the reasons I expected. As one manager took the time to explain to me, they were forced into reducing the workforce by executive leaders in spite of their objections, and had very little say in the process. Their reaction to my memo wasn’t just damage control. They were hurt because they had done their best with what little control they had over the process.
While it felt cathartic to publish the memo, in hindsight I regret the way I handled things. I’d never been in the shoes of a manager whose bosses are demanding they fire people, so I hadn’t considered how my words would impact them. Nor could I have any idea what the investors, board members, and executives really discussed that led them to mandate layoffs. Perhaps if they hadn’t cut jobs, the company would have failed right then and there, costing everyone their employment. Then again, maybe not.
If I want to find out whether a better way to do business exists, I need to dive deeper into the system and understand how it really works. Win or lose, I’ll come out the other side better educated.
A seat at the table
The full-time employee hiring process generally involves very little negotiation. If you’re an enterprising senior contributor you might be able to negotiate your salary. If you’re negotiating benefits or incentives, your prospective title probably starts with “C” and ends with “O”. For most other jobs the company more or less hands you the contract and gives you two options: sign it, or work elsewhere. Plus, employment in most U.S. states is “at-will,” which creates a lot of risk and uncertainty for both employees and companies.
I didn’t think much of this as a junior engineer hungry for any chance to learn on the job, but today that dynamic feels incredibily limiting. I have in-demand skills, I know when and how I work best, and I’m pretty darn adaptable. Why am I giving up so much control?
Now, am I excited to comb through lengthy contracts, pay for my own health insurance, and manage my own taxes? Not entirely, though I admit I’m morbidly curious. Nevertheless, I am excited to find myself with a seat at the table, negotiating as an equal with some degree of real influence.
More baskets for my eggs
Early in my career, I viewed a full-time, salaried job as the pinnacle of stability. When the economy is booming, that might be true. But let’s consider employment as a form of investment for a moment. A single, full-time job is kind of like investing your entire “employment” portfolio in a single stock. As long as that stock is gaining value and paying dividends, you’re golden. But if and when it nosedives, you can lose everything overnight.
(Side note, this is the same rationale behind the advice to sell off your employee stock shares as soon as they vest.)
From what I’ve heard, freelancing is really tough when you’re starting out. You’re constantly struggling to find new leads, win contracts, and build a portfolio that inspires trust. However, the cash flow of a successful freelancer is better hedged than a full-time employee’s. With multiple regular or recurring clients, you can rest a little easier knowing that even if one contract terminates, you still have the others. Plus, freelance contracts are more explicit about early termination, which can give you crucial buffer time and money to find more work.
No regrets
It’s quite possible that I never find the ideal way of working that I’ve described. Maybe it doesn’t even exist. The thing is, I can’t know unless I try! And that’s the real driving force behind my decision. If I don’t try, I just know I’m going to regret it.
Gratitudes
I need to give a bunch of shoutouts to everyone who’s helped me make this decision. Foremost, thank you to my partner, my family, and my friends who have all patiently supported me while I wavered anxiously back and forth. Their listening skills, life experiences, and great ideas have been invaluable. I love you all very much and I am eternally grateful to be so lucky! Next, I want to thank everyone in my professional network who took the time to speak with me, share their experiences, and answer my questions at every stage of contemplatation. I have honestly been overwhelmed by the power of my network. I’m not naming any names because the internet is currently one big piñata of personally identifiable information and this is a publicly accessible website, but you know who you are!