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The Freelance Diaries: The Caffeinated Project Manager

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As part of the series on earning more money, today’s Money Diaries — actually, today’s Freelance Diaries — is from a project manager who left his fulltime job to work as a freelancer.

Below, you’ll notice:

  • He now makes 3 times what he made at his fulltime job — but he still nets less overall
  • His tactics for managing his clients
  • Weaving lifestyle (video games from 3:30pm – 6:00pm) with work

Be sure to sign up at Earn1k to get specific scripts on increasing your rates, managing clients, and using psychology against yourself to keep motivated.

* * *


“I’m a freelance project manager. Which I know sounds weird. Project management, I always thought, was one of those made-up corporate jobs, kind of like that one guy from Office Space who deals with people so the engineers don’t have to. You’ve seen it, right? Of course you have.

In reality, project management basically just means I get paid to make sure things get done. It’s incredibly valuable to companies that are disorganized or run tight deadlines. The hard part is packaging it because it’s not often perceived as high-value (kind of like how most people think they know how to write well).

The trick for me is, I never position myself as a project manager when first pitching to a client. I’m usually brought on to do something small, like a writing project or a PR project. At some point, the client realizes their organization/communication flow used to suck and I’m making it better. So after that I usually just end up being a project manager. That’s the classic “sell them what they want, give them what they need” technique, I guess.

Anyways, here’s my Diary.”

Day 1

6 am: Wake up. Yeahhh, freelancing doesn’t always mean you get to sleep all day. Although sometimes it does!

7am: Drive over to a coffee shop to start working. I have noticed that good, work-friendly coffee shops (meaning they don’t have screaming children or broken tables) are rare. The only one in town worth going to costs $5 a cup, and parking there sucks. But it’s worth it. My time is important, so I try to save it any way I can.

8am: I spend a few hours at the coffee shop doing some work, following up on deadlines, shooting emails. No interruptions or random requests from clients, which is nice. I know you’re not supposed to leave your email open all day (the 4-Hour Workweek people tell me so) but whatever. I like to be responsive to clients, and I have a good process for handling email already.

2pm: My productivity level is dropping off. I guess that’s why I get up at 6 to work. Once I hit that “I don’t feel like working anymore” zone, I usually stop and pick it back up in the evening. So I drive home.

3:30pm – 6pm: Playing video games… nothing to see here. Man, I don’t miss my old job.

12 am: I catch up on some work. I’ve figured out that I do my best creative work at night, and like to power through stuff (menial work, invoicing, etc.) in the mornings. I’m a big believer in finding out what times you do your best work, then sticking to that.

Day 2

8am: I check my messages and see that I have one from my client (I turn off my phone at night. Boundaries, you know?). Apparently, he got his laptop stolen. Oh, and he wasn’t backing his stuff up, despite my recommendations to do so, so we’ll fall behind on one of our projects. Great.

Sometimes, clients will simply not do what you recommend – EVEN WHEN THEY AGREE WITH IT. They just ignore stuff. You have to live with that, I guess. Sometimes it’s not just about telling your clients what they should do, or lecturing them – it’s also being realistic about what they WILL do and working around that.

9am: At the coffee shop again. I work best in 4-hour bursts.

6pm: And yet, I’m still here… so I go home after sending a weekly email update to my clients. They don’t ask for it, but they always respond well and seem to like knowing what I’m doing. I guess it’s better than them wondering what I’m up to.

Day 3

10 am: Irritating. I like my client, but he absolutely doesn’t take ANY time to spell check his emails. I get something like this:

“cn weht \ time tmr?

Or what si itcan you telme minalkj


WHAT??? I’m not sure what to do with this. Usually I reply to confirm what I think he’s saying. I can’t really think of a nice way to say “Hey, it would really make me less irritated all the time if you spell-checked your emails.”

1pm: Write a pitch to a new prospect. Let’s see if it works out. I don’t pitch that often (I’m pretty happy with my current clients) but you never know what will be the next big thing, I guess. I keep the door open for stuff like that.

2pm: I have a tip – always, always keep track of what you spend your hours on, even if you think your client doesn’t care about the little details. My client never asked me before, then he suddenly calls me and is like “Hey these 20 hours – what are they for?”

It wasn’t a big deal, and of course I figured it out eventually but for a few seconds I was like “UHHHH… hm…” Lesson learned.

4pm: Here’s another tip: don’t drink and work.

Day 4

10 am: Spend 2 hours on a conference call with clients. They’re always traveling and in different time zones, so finding time to chat is difficult. Plus the calls themselves are pretty useless. I’ve realized that sometimes, clients just want someone to talk to and explain every little detail of what they’re doing. I’m like their therapist.

1pm: Finished writing a ridiculously long email with detailed notes from our call. Send it off to the clients, because they’re horribly unorganized (still). I can tell it helps them think about things more clearly, and they appreciate it a LOT.

These guys are really gushy too. They reply back with things like:

“Thank you SO SO SOOOO much for this.”

“thanks… you are incredibly professional and thoughtful and I am deeply grateful for your hard work and dedication.”

Good. I keep all this stuff in mind when it comes time to raise my rates.

9pm: My parents, both engineers, don’t really get what I do. I just tell them I do business stuff. They always ask me if I need money.

I guess it’s nice to know I have a safety net. I’m not opposed to the idea of asking for help if I need it – I’m just not that prideful I guess.

Day 5

11 am: Some days I just don’t feel like working. So I won’t today. It’s Friday, which is practically Saturday anyways. Ah, freelancing is nice after all.

People always go “wahh lucky” when I tell them stuff like this and I’m like hey screw you. I don’t get paid vacation and sick days, you ass. And it wasn’t just luck (although I admit luck helps).

1pm: As I write this, I’m thinking: It’s good to have flexibility. It’s good for my motivation. Now, when I take a day off, I usually charge into the next day with a roar and get really pumped up about knocking out work tasks. It was the opposite when I used to work as a management consultant at a top-tier firm. I dreaded Monday mornings.

I haven’t done a detailed analysis of the numbers, but I estimate that back then, I worked 60 hours a week (I worked from home all the time) for 50 weeks = 3000 hours. Let’s take my salary, around 60K, that makes my time roughly worth $20/hr.

Now I work fewer hours (about 40), and I charge $60/hr. And while you might think, Wow! $60/hour, that’s like $120,000 a year! You’re way richer now! No, because less than half of those hours are chargeable. Plus, I haven’t factored in benefits, 401(k) matching and the biggie: paid health insurance. All things factored in, I’m still making less than before.

Yeah, sorry to be a downer. But hey, new businesses take time to grow and things are looking positive so far. And I’m increasing my rates this year.

Day 6

11 am: It’s Saturday now, which basically means nothing to me. Back to the coffee shop. Most of the time, I work 7 days a week.

3pm: That’s as good a time as any to call it a day, at least for the client work.

4pm: One thing I like about my work is I can spend more free time on other, “riskier” business ventures. Right now a partner and I are working on a new product together, so I do some of the market research work at home for a few hours.

Day 7

1pm: On Sundays, I like to spend some time learning new things. Right now I’m watching a training program on product development. Very interesting stuff.

It’s hard to get over the fact that I’d be paid to watch this if I had a real job – instead I’m paying for it myself. But I really believe in consistently gaining new skills in order to grow.

4pm: Writing a Craigslist post for some help the clients want to hire. Not really what I was hired to do, but if they’re paying, I won’t complain. Yet another reason why I like charging by the hour – too many variables in project pricing.

5pm: I invoice one client, clean up my notes, and get ready for tomorrow.

* * *

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  1. Elizabeth Godwin Link to this comment

    Thanks for this! It’s cool to see how someone prioritizes their day when they don’t actually go to an office with a boss. I am in love with this earning more money series.

  2. I’m fascinated by this idea of freelance project management. ANy chance we could get more details on the actual acquisition of new clients with this idea of coming in as a writer but then doing PM stuff?

    • Hi Writer’s Coin, Did you get a reply to you question about the acquisition of new clients?

  3. I think this idea is great. Honestly, I would be interested in freelance project managing if I don’t start my own business entirely.

  4. Ramit, you cad!

    During your office hours someone mentioned freelancing as a project manager and you were all “Dude, seriously. Project management?! What does a project manager even do?”

  5. Actually, this sounds like a really valuable service – assuming that the project manager gets results and has a reasonable price point. I agree with writers coin – it would be nice to get some specifics – not only on getting clients, but how you solve specific client problems. It seems that someone with proven expertise in e-commerce product sales and setup would be invaluable in getting an e-storefront up and running.

  6. Clearly, it’s not all glitz and glamour. Thanks for sharing your story, PM guy.

  7. I like that he points out the positives and negatives. I tend to ignore anything that paints freelancing as a perfect situation or as being totally not worth it.

  8. I also agree with Writer’s Coin. I am extremely interested in how the author finds potential clients. How does he advertise? What sort of businesses require his services? Are they mostly small ones?

    This seems like something I could easily do in my free time. I’m already fairly rigorously trained in project management at work.

    • Hi Writer’s Coin, Did you get a reply to your question about the acquisition of new clients?

  9. This is the first one of the ‘Money Diaries’ that I’ve truly enjoyed. Most of the other people seem like numb skulls.

    One thing this reminded me is that I want to learn a successful way to research different proprietary training programs. How do I know which one to choose? Do I go solely based on the reviews? There seems to be almost TOO many choices.

  10. I’m a certified Project Manager, have been since 2005. I’m curious what part of the country this guy is in. $60/hr actually seems a bit low, and as a PM, if you don’t bill for all of your hours, your estimates for project work will be too low, and never duplicate-able. How does the writer manage for that? But also, only billing half of your hours seems like it might be cutting yourself way short.
    I’m glad to see this article!
    Continue the great work Ramit!