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Happier Freelancing


“I’m not enjoying freelancing. It was supposed to be this amazing blend of great money and freedom, but I find myself stressed, bored, or overworked. I’m either chasing down invoices, hustling after new work, or discouraged at yet another wordpress install.” – most freelancers at some point

There are many highs of freelancing: big paychecks, flexible work hours, no boss, and a continually changing environment. There are many lows as well: unpaid invoices, horrible clients, challenges in finding work, and a lack of motivation to finish that dull gig you did land.

Being happy with your freelancing career comes down to managing these realities, and before you can extend and grow the positive aspects, you have to learn to manage the bad.

  1. Cashflow Troubles
    If you’re like every other freelancer out there you’ve had issues with cashflow at some point. Whether it’s being forced to wait for a check to clear, searching for that check in the first place, or being disappointed at how small it is when it finally shows up, fixing your cashflow issues will do wonders for your stress levels.
    If you bill monthly, push for bi-weekly. If you don’t have a penalty clause for late payments, add one in. If you never seem to have enough money, raise your rates. Even an extra $5/hr can help and that’s almost always an easy change to make. The goal here isn’t to drastically change things overnight, but to build a habit of continually improving this part of your business and not letting it grow stale.
  2. Client Troubles
    Client issues can drain you far past exhaustion. Let’s be clear: you’re not doing a good job by toughing out a bad experience; you’re letting yourself and your client down. Is your client being completely unreasonable and demanding? Communicate that clearly and objectively. You’ll either improve the situation or confirm it’s untenable and more severe changes are necessary.
    Many client issues can be prevented by more upfront communication: very clear statements of what you will and will not do, what you will delivery by when, and what your expectations are for their involvement. Most people want to succeed and need your help to do so. Things just devolve when it’s unfamiliar territory for both sides.
    Of course, it’s easier to follow this advice when each individual gig doesn’t carry a “I need this for rent” subtext. That’s another reason point #1 is so important: if you can’t fire a bad client because you need the money, you’re at their mercy.
  3. Finding Work
    This is many freelancer’s #1 challenge, and there’s no easy fix. Still, there are many things you can do to make it better:

    1. Network: past clients, current friends, future partners, all can be valuable and help you find that next gig
    2. Get involved in online forums like reddit.com/r/freelance
    3. Follow people in your industry and see what they’re kicking around. Often they’re happy to talk about their projects or give you a tip on yours
    4. Look for chances to build in recurring payments. Brennan and Patrick McKenzie are putting together something directly focused on this, see details here
  4. As challenging as it is, if you don’t improve your ability to find work, you will always end a project with a check and a reawakening of that “what’s next” anxiety. Remember: it’s not good enough to be great at what you do. You can’t sit back and just watch the requests come in.

Once you’ve gotten the basics managed, take a look at the psychological aspects of your business. They are just as real as issues like cashflow.

Lack of Motivation

A solid, repeatable routine provides a variety of benefits. Unfortunately, it can get too comfortable, and pretty soon you’re only billing 20hrs a week, getting a bit too good at Call of Duty, and packing on some weight as well. What gives?

Congrats, you’ve had enough success to enable one of the first world freelancer challenges: “I can’t get motivated to work on my own stuff anymore…”

This takes grit, but you have to be honest with yourself, free of distraction. Take a long walk or bike ride, just get out of your usual setting. Nature’s great for this, but even a stroll down an unfamiliar street can disengage your normal neural flows.

I like to play to my strengths in situations like this. I have a fairly analytical mind, so playing an objective “ok Me, what’s up?” can often be fruitful. You’ll have to learn to actually require a real answer of yourself, and have it be specific, but if you can get there you’ll usually discover something that wasn’t obvious a little while ago. “Why am I feeling adrift? Am I even feeling adrift or just a bit down? Am I really trying to push myself forward? Do I even like my framework of choice?”

If you find this kind of self reflection challenging, ask a friend. The important thing is to stop the normal routine, as it got you in this place.

If you find yourself carrying a lot of stress, treat yourself to a massage. Every single time I get one I leave saying “I’m an idiot for not doing this sooner”.

Feeling Adrift

I think this happens to most of us, perhaps even multiple times throughout our careers. That freedom you value so highly has a cost, and it’s a lack of anchoring to a more traditional work environment and company.

Like it or not, the world is still designed for a 9-5 mentality, and doing your own thing can get a bit lonely. If you don’t keep watch over these types of feelings, you can easily wake up someday and ask yourself “what am I doing”, especially when you find out that banks won’t look at your income the same as W2 income, when you realize how much that insurance perk you used to scoff at actually costs.

The best way to handle these types of feelings are to counteract them directly. If you’re feeling adrift, ask yourself why? Do you wish you were progressing more towards a goal? Do you have a goal to progress to?

Most people don’t freelance forever. They’ll end up at a company, create a consultancy, build a startup, etc. If you’re not sure what you want to do, that’s ok, but if you’re stressed about it you’ll want to try to set out some plans and a path towards a goal. It might just be “see if I want to manage a small consultancy” and start by working with some subcontractors.

Moving Forward

When you’re in a good place, down on increasing the positive aspects of your career. Grab coffee with some local freelancers, write that guest blog post, give a talk at a local meetup.

It’s hard to summon the energy to be proactive when you’re deep in the weeds, and it can be easy to disregard them when things are good, but remember: you manage your career and development as a freelancer, no one else, and you don’t want years to go by where you haven’t learned something new.

Just as managing the business is your responsibility, so is managing your happiness. If you can mitigate the tough times, grow in the good times, and remember to take a moment now and then to enjoy yourself, you can create the right blend of stability and security that leads to a happy freelancing life.

 

Jack is a startup founder, consultant, and the creator of Freelancing.io, a curated platform for freelancers. He blogs at http://jackdempsey.me and is occasionally interesting on Twitter @jackdempsey

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