Ask the Bitches: My Boss Won’t Give Me a Contract and I’m Freaking Out

We have another reader question today.

On its face, it’s a pretty straightforward question about working sans contract. But beneath bubble some pretty volcanic emotions about job security, class, and anxiety. Let’s get into it!

Our reader asks…

I was hired to write blog posts for a digital platform. I was offered $15 an hour and 20-30 hours per week, paid out once a month as a direct deposit. That was a year and a half ago.

Since then, my responsibilities have changed tremendously. Instead of writing a few blog posts per week, I also work on site maintenance and other freelancers’ blog posts. I feel like I’m more involved with the administrative side of the blog than some of the other freelance writers I’ve seen, but I can’t confirm this, as I have no regular correspondence with any of my peers.

I was told I was being hired as a freelance writer, and that there would be a contract to be signed. That contract still hasn’t come. I asked about it when I was first hired and the CEO said he’d get around to it and never did. I was getting paid, so I didn’t care enough to push the issue and eventually forgot. But now I feel less like a freelance content creator and more like a full-time member of the creative staff. I asked the CEO a month or two ago about the contract again, and he dodged me. Again.

The rational side of me knows that I’m well within my rights to renegotiate where I stand with this company. I want to stand up for myself. But every time I fire up the email draft, I get so physically ill I have to walk away. Just writing this makes me want to puke.

I feel like I’m biting the hand that feeds me by saying it’s not enough. I feel like if I ask and get an outright refusal, I’ll either be forced to stay and feel undervalued or leave and go back to Minimum Wage Hell. Worrying about it is taking a toll on my health. I feel like a mess and a fool and a bastard and a failure all wrapped up in one big blanket of anxiety and ennui.

According to The Creative Group’s 2016 salary guide, bloggers should be making $45k a year but that just seems insane to me. That’s not the kind of money people like me make. We make minimum wage where I come from and we like it. $15 an hour is unthinkable enough, but a salaried position? Benefits? That’s not stuff I or anyone in my family has ever had to deal with going back generations. I don’t know how to not be in poverty. No one ever told me that was an option.

I feel kind of ashamed seeing it all in writing, if I’m honest. I feel weak, like I should be able to figure this out on my own. But I’m so grateful that I don’t have to. I can’t tell you what it means to have someone in my financial corner. I’ve never had that. I wish I’d found you guys years ago.

-Claire

Our advice

I think the first thing Claire needs to hear is: omg, chill.

I really try hard not to tell people experiencing anxiety to chill. But this case warrants it!

Claire’s framed her situation thusly: “I fear I’m being taken advantage of, but I’m scared of asking for more because if I lose this job I will be trapped in an endless cycle of generational poverty. My uncertainty is evidence of the fact that I’m a massive failure. I see a train coming and I lack the courage to get off the tracks. I deserve to be smashed to itty bitty pieces and become a cautionary tale to future generations of children who dare to harbor secret dreams of improving their station.”

That is about 16,000% more Freaking the Fuck Out than the situation warrants. We save that level of Freaking the Fuck Out for people who, like, fled the scene of a fatal accident involving a pedestrian. Your life isn’t ruined—it’s just getting started.

Here is how I would reframe it: “My current financial situation is stable and promising. I like my job and I’m learning new skills. But certain factors make it feel tenuous, and it scares me to imagine what would happen if that opportunity went away. I’m not sure how to make myself more secure so I can enjoy my good fortune, instead of stressing about when it might go away.”

Contracts are just a red herring

Never do work without a contract. Never. Not even if client is your mom. Especially if it’s your mom!

That said, everyone has done it. Hell, I’ve done it this year, and I absolutely know better! It’s a tragic rite of passage. You need to get burned before you can appreciate good advice re: the touching of hot stoves. Although it’s unpleasant now, I can pretty much guarantee this is the last job you’ll ever undertake without a contract. That makes this a productive, normal, age-appropriate lesson to learn.

Marie Kondo commands us to thank the objects we throw away, for each one taught us something about ourselves. Use the same mentality here. Mistakes like this aren’t a sign you’re a failure—they are crucial lessons upon which you will build your future successes. Nobody taught you this shit, and now you know. Good job! You may officially stop beating yourself up for this.

And, in this case, it doesn’t seem to be the real problem. You’re getting paid, in full and on time. Given that, it’s my guess that your CEO isn’t dodging you for sinister reasons. Odds are good he’s just an extremely busy, distractible man with a thousand more pressing issues on his mind. Its chief evil seems to be that it’s amping up your sense of uncertainty.

You don’t have job security—but who does?

Here’s the thing though… Even if you had a signed contract, you would still not have job security.

I have a good job, with a handsome salary and benefits, plus several years worth of extremely positive assessments in my file. And I could be handed my walking papers tomorrow, for almost any reason, including no reason at all. That’s the case for almost all workers in almost all states.

It’s called at will employment. Unless your employer is firing you for illegal reasons, you have very little legal recourse for objecting to your termination. They can’t discriminate for protected characteristics, like race and gender; but they don’t have to demonstrate a “good” reason for letting you go. As with romance, it takes two parties to agree to be in a relationship, but only one to break up.

If you want job security, a contract won’t give it to you. A single employer won’t give it to you, either. Our grandparents might’ve worked for the same employer for decades, then retired with a pension. Sadly, that kind of job security is almost completely extinct.

In this new economy, true security comes from you. There are tons of strategies to build it.

• Make yourself irreplaceable in your current workplace. Learn to do things no one else can do. Memorize arcane systems that nobody else wants to touch. Build relationships with vendors that nobody can replicate. Gain tons of specialized skills and knowledge. And you’ll be the last one they lay off when hard times hit.
• Make yourself attractive to many potential employers. Build a skill set that every workplace needs. Pursue education in in-demand fields. Keep your network fresh and always be low-key looking for the next thing.
• Become your own boss. Monetize your hobbies. Keep other options on the back burner. Decide how much to focus on developing them.
• Keep your commitments low. Limit your spending overall and learn to be happy with less.
• Build an emergency fund. It lessens the impact of losing a job, getting sick, or needing a break.

Check out our article on preparing for a recession, as there’s a lot of overlap:

• How Do I Prepare for a Recession?

The freelancer’s path versus the employee’s path

Let’s get back to Claire’s unique conundrum. She has a choice here: seek full-time employment, or grow as a freelancer. Quickly, here are some of the key differences:

Freelancers usually…

• work with many clients
• set their own rates, and are paid more by the hour
• don’t receive benefits like health insurance
• pay self-employment tax, and often have a big tax bill in April
• work independently, without a lot of oversight
• are expected to know how to do their jobs without training
• can subcontract work out to other people
• decide their own hours and work remotely
• get to choose their clients, projects, and duties
• ideal for people with great ambition and hustle (Slytherins and Gryffindors)

Employees usually…

• have just one client
• get a predictable paycheck, but are paid less by the hour
• have benefits like health insurance
• have income tax deducted automatically from their paychecks, and might owe little or no taxes in April, or even get some money back
• receive much more direct instructions about how to do their jobs
• receive ongoing education and training
• need to do their own damn work
• work set hours in one physical location
• can’t pick and choose the projects they work on or the people they work with
• ideal for people who want predictable outcomes (Hufflepuffs and Ravenclaws)

In the current situation, either of these are extremely doable. You just have to choose which one you want to pursue. (The other can always be a fallback. It’s good to have options!)

Nobody knows what you want if you don’t tell them

Here’s what your CEO currently knows about you:

• You have worked for him for 1.5 years
• You would like a contract

Realistically, that’s it. Here’s information he’s likely missing:

• Are you happy in your work?
• What do you need out of this job?
• What are your career aspirations?
• Are your supervisors happy with you?
• What skills do you want to gain?
• How over- or under-worked are you?
• Do you like working alone?
• Does your current workload satisfy or frustrate you?
• Are you consistently hitting your 20-30 hour mark?
• Do you expect a regular cost of living raise?
• Do you expect an annual rate increase?
• How do you feel about the digital platform he built?
• What are you afraid of?
• What do you need from him?

I had a (good) boss who used to end every weekly check-in call with this question: “What do you need my help with?” My best talks with her were sessions where I came in prepared to answer that question honestly.

The fact that Claire wants more money and stability in her life is achingly, blindingly obvious to us. But that doesn’t mean it’s obvious to her boss.

If you need something from someone, you must ask.

Anatomy of an ask

Set up a meeting

Ask your CEO to talk to you. Asking via email is fine, but the talk itself should be either  in person or over the phone.

“Hi Big Dave! Can I put half an hour on your calendar this week? I’m sure we won’t need the full time, I just wanted to have a check-in with you. Are you free anytime on Tuesday or Thursday after 1PM?”

Make humanoid pleasantries

Real talk: when I have an agenda, I rush by basic niceties. But that’s the stuff that builds relationships. And a little small talk will help warm both of you up.

“Hi Big Dave! It’s been a while since we had a chance to catch up. How are you? How ready are you for this winter to be over? Hoo boy, weather!”

Get to the point

Thank him for making time and tell him directly what it is you want.

“Thanks again for setting aside time to chat with me. The reason I wanted to talk is because…”

If you want to ask for a raise in order to keep doing the same work:

“I’ve been with Big Dave’s E-Terrariums for about a year and a half now. I’m more experienced than when you first hired me, so I’m letting all my existing clients know that I plan to raise my rates by 10% across the board starting in Q2. I love having you as a client, and I really appreciate you taking a risk on a fresh-faced writer, so I wanted to make sure I gave you plenty of notice.”

If he says no: “Totally understandable. I’m glad I asked. With that in mind, let’s continue at our current rate for now. There may come a point where I need to scale back to focus on my other clients. If I get to that point, I’ll be sure to give you a heads up.”

If you want to add more freelancing clients to your pool:

“Big Dave, I’m trying to grow the number of clients I have. You guys have been a great resource, and I’d ideally love to have more clients like you. So I wanted to pick your brain a bit about how and where you find your freelance team. What could I do to present a stronger portfolio or online presence to someone like you?

“And, if you wouldn’t mind—if you’ve liked working with me, could I ask you to write a LinkedIn recommendation for me? People really care about that kind of thing, and I’m sure that a few words from you would carry a lot of weight.”

If he says no: He will not say no. This question is ingeniously designed to flatter him.

If you want to signal your interest in a full-time position:

“Big Dave, when I started here last September, our agreement was 20-30 hours of content writing only. Since then, I’ve consistently been going over my allotted hours, and my work has grown to include a lot of duties outside of that original scope. I’m fine with that, because I actually really enjoy the team and the work, and I really believe that our E-Terrarriums are the best virtual terrariums on the Net.

“Tell me a little bit about what your plans are. If your intention is to grow the team again in the future, would you consider me for a full-time role? I’d definitely be interested.”

If he says no: “Totally cool. Given that, could we make a plan to ease back to a maximum of 30 hours per week so I have a predictable time slot to dedicate to other clients? And obviously, if you ever change your plans, please keep me in mind.”

If you really just want him to give you a goddamn contract:

“Big Dave, the reason I’m calling is because of our lack of a formal contract. I hate to be a pest, but I really need to have a contract on file because…”

I give you permission to tell a white lie that will give you a plausible reason to ask now and not let up until you get it.

“…I’m trying to sign the lease on a new apartment, and they’ve asked for some documentation regarding my income.”

Or…

“…my tax preparer wants me to have clear documentation regarding which work is contractual and which is true employment. I really need documentation that reflects that my relationship with Big Dave’s E-Terrariums is on a freelance basis.”

If he says no: Wait two days, and send an email about “following up on our earlier conversation…” and remind him. Repeat this every two days until either (A) he coughs it up or (B) you become a cobweb-covered skeleton.

Aim higher

You already know you have a Whole Fucking Situation with some serious imposter syndrome. Girl. Your letter makes it clear that you are not only petrified, but extremely self-aware of your own petrification.

Ask yourself this: “I know what my problem is. So what am I doing to work on it?”

Fixing your busted-ass sense of self-worth is harder to do than getting a raise or getting a new job. But it’s also the only thing over which you have direct control.

Your boss may not be able to give you a raise right now; your company may fold next week; the national economy may tank; the whole planet could be hit by an asteroid. Much in this life is completely out of your control. But you get to decide how much to respect yourself.

Self respect is not an innate yes/no quality, like having brown eyes or a luscious butt. It’s a skill, like playing an instrument. You must practice it; learn it; let it get rusty; polish it up again.

If you want your life to change, you have to try to do something different. The clouds ain’t gonna part one day and shower you in a strong sense of self-worth. No one will ever give you a $50/hour gig because you quietly accepted enough $15/hour gigs.

• Santa Isn’t Coming and Neither Is Your Promotion: How To Get Promoted
• You Need to Ask for a Fucking Raise
• The First Time I Asked for a Raise
• Should Artists Ever Work for Free?
• Stop Undervaluing Your Freelance Work, You Darling Fool
• Freelancer, Protect Thyself… With a Fair Contract
• My Secret Weapon for Preparing for Awkward Boss Confrontations

Learn the skill of self-respect

There is so much you can do. There’s therapy, but that’s only one idea. Here is some free stuff you can do:

• Mentor or volunteer to help people who are even worse off than you. Many people learn how to advocate for themselves by advocating for others.
• Seek out social communities of like-minded people who have a positive, productive, helpful vibe. Ditch the shit that’s just more-funnier group whining.
• Read books and blogs and listen to podcasts and videos that give you positive messages about the validity of your own ambitions.
• Listen to music that will pump your ass up for forcing yourself through those uncomfortable calls to the boss.
• Write in a journal, meditate, repeat mantras, pray, or talk to a confidant about the roots of your fears.
• Find mentors who can fill the knowledge gaps your family maybe can’t. They can be real people mentors, fake internet mentors (like us!), or even famous/fictional heroes with a wealth of writing or speaking to draw upon.
• Develop friendships with people who have different backgrounds and skills than you do. Learn from them.
• Make less space in your life for people who hold you back by expecting less of you. Make more space for the people who see your infinite potential.
• Do physical things to reward and respect your body, like exercising or cooking yourself a healthy meal or slamming a bunch of relaxing-ass brewskis. I did all three today! Whatever, embrace the chaos!
• Pursue hobbies that make you feel like you’re making a positive difference in the world.
• Move out. If you’re still in your parents’ home, or your childhood hometown, or your first apartment, go anywhere else. I can still feel all the feelings I felt there when I walk into an old space. I can feel myself becoming that weak sauce 1.0 version of myself on the rare occasions I visit. If applicable and possible, GTFO.
• Ask people for help and let them give it.

These are just some ideas. A lot of overlap from this list:

• Our Master List of 100% Free Mental Health Self-Care Tactics

You don’t get just one opportunity

When you’re given your first real job opportunity, it’s gonna feel really high stakes. “I am the beneficiary of a happy accident and if I fuck it up the record will scratch and everyone will stare and realize that they made a mistake and I don’t belong here!” I certainly felt that way.

But a wonderful thing will happen as you get older. You will realize that your first opportunity wasn’t also your last one. More and better ones will follow.

Conversely, you’ll meet many people with fantastic jobs who are scatterbrained, cantankerous, stubborn, selfish, reactive, unskilled, and unreliable. And they get to keep those great jobs because why? Shrug! Jobs aren’t an external manifestation of inner worthiness and good karma. They’re just jobs.

Finally, I will say that there are some employers who are petty and vindictive enough to want to replace an employee who asks for a raise, or greater role clarity, or a contract. Those are people you definitely don’t want to work for. They are erratic, and liable to fire you for any number of reasons. Their toxicity will reach its tentacles into your private life and sup upon all of your little joys. If you’re in that situation, get out as soon as you can.

But for the average employer, replacing an employee—even a sucky employee—is a pain in the ass. It’s a lot of work to post job listings, vet candidates, on-board them, and get them fully up to speed. It could take Claire’s CEO six months to get someone performing at her level. And he’s taking a risk that this new employee might suck, even after investing all that time. Given that, most employers will decide they’d much rather pay more to keep you.

That’s all for today! If you want us to answer your questions, please become a Patreon supporter. It lets us focus on doing what we love: helping all of y’all!