The first 60 days: the successes and challenges of being self-employed
For those of you following along, you’ll remember that two months ago I left my job at Palantir.net. Over the course of the last two months, I’ve noted some of the challenges and successes I’ve experienced along the way, and wanted to share.
I’d also like to note that much of what I do is creative and/or art-based. As such, while some basic business fundamentals can and should apply, it’s also simply different than most service or product-based businesses. And that’s ok.
Developing repeatable processes around how you handle aspect of your business (sales, fulfillment, invoicing, etc) is never a bad thing, as it can ease the pain of those tasks and allow you to get back to what you should be doing. But I also don’t think creating and sticking to some of these kinds of processes is not entirely possible for some people and their businesses. In any case, the things...
1) Focus: so, so many things!
I’m no stranger to working for myself, and even during my time as an employee of a company I was moonlighting as an artist and designer, but coming back to it has been eye-opening from a ‘stay on target’ standpoint.
Yes, I like keeping busy. Yes, I like a wide variety of types of work. But prioritization, follow-ups, business development, and then, of course, actually doing the work... is a lot. WAY. TOO. MUCH... some days.
The big caveat here is that I should be so lucky to have THAT many opportunities, so please know that I’m not complaining. I’m embracing a challenge that faces a personality type like mine as to understand it, wrassle it, and ultimately become a better person and worker.
I’m also purposefully taking on too much for this first phase of my self-employment journey to: 1) make money, 2) understand what is the most rewarding, and 3) overcome my own blockers and learn new things
While maintaining focus isn’t entirely solved just yet, here’s how I’ve been able to help myself a lot so far:
Inbox zero! More on that later...
Google Keep is amazing. I really, really enjoy it. I could use Trello or Basecamp (love those, too) but Keep is super simple and easy to access from anywhere. It’s all I need for now.
Establishing a clear priority list, and being ruthless with prioritization (as in not always what I WANT to do, but rather what I NEED to do). First, I have a big picture week overview to catalog the things I need to consider for that week. I list them to make sure they don’t fall through the cracks. Then, knowing my own limitations, I can only really only do up to 3 bigger things in a day (since each of those things likely has sub-to dos). That can be a lot, but the goal is to finish each of those on that day. I also then have 3 secondary “filler” things that I list, knowing I do not actually have to get to them if time doesn’t allow. If I do, bonus. But if I don’t I reevaluate and decide how important they are for the next day, and move them accordingly. Unless something is super important (since stuff does pop up unexpectedly) I try not to deviate from this approach. It’s the general rule.
I use a Customer Relationship Management tool for sales tracking. I know, it’s super businessy, but since I have a variety of revenue streams it’s super important I track where my money is coming from, where I am in the sales process on a potential project, other project details, and how much money is arriving and when. I use HubSpot CRM because it’s free (except for the deluge of email marketing), but there are plenty of others (I also love Pipedrive, and it’s cheap if you don’t do well with a cluttered inbox).
Maintaining a consistent schedule. More on that later.
2) Inbox zero is the best!
We all know this in theory, some in practice. I always found it difficult until my pal Fitz explained it in a way that finally made sense. It’s a combination of using some principles from the site Getting Things Done (this flowchart is pretty great), particularly the labels and then following through on them.
Fitz adds an @ sign in front of his labels to ensure they’re at the top of his labels list in Gmail. I opted for these labels: @ACTION, @WAITING, @IMPORTANT, @PERSONAL, and @RESKETCH. Action is just that; action is required. Waiting is stuff that I can’t act on just yet because I’m waiting on a response or some other dependency. Important is admittedly a bit redundant, but I like it because it allows me to tag things that I don’t want to forget but doesn’t necessarily require action or that I’m waiting on. Things like insurance info, something from my account that I want to track for a bit, and other such important things. Personal is important so emails from family and friends don’t get lost or mixed with business. And once and I awhile I get a Resketch email to my main email account, so while I typically forward those and deal with on the Resketch side, sometimes there’s overlap so I track them for awhile and THEN delete or archive.
The idea is that you route emails accordingly and clear out your inbox to zero BUT then actually deal with the emails you’ve routed accordingly, and get those to zero, too. Be ruthless. This is YOUR inbox. You’ll feel better if you do.
And remember to unsubscribe from shit you don’t want or mark as junk those emails that are unsolicited marketing crap. Except the stuff from Nigerian Princes. That stuff is golden and super legit.
PS - Fitz also uses Gmail snooze but I have yet to implement.
3) Making confident choices
This isn’t always easy for me, but it’s important. If you don’t want to do something for a reason you know in your heart to be valid, don’t do it. In the past I would second guess myself or think I should do something, but would almost ALWAYS regret it.
Having a clear mission and goals articulated helps a lot. Ask yourself: is this going to move me forward? Is it fulfilling in some tangible way that will make me happier or help achieve my goals? If not, kindly say no thanks, and move on to what matters.
Admittedly this is easier said than done if you need money, right?
I like what some folks utilize to help decide whether or not a project is worth pursuing: 1) is it the right fit? 2) is it profitable? and 3) is it compelling and/or cool? If I remember correctly, the idea is that if only one of these questions is a yes, it’s not worth pursuing. If two are a yes, it’s likely worth going for. And if all three are a yes, then absolutely!
4) Cash flow can be frustrating
This is a natural segue. Cash flow can be super frustrating. The money is on its way, but due to lead times or payment terms it may not appear for a couple weeks or a couple of months.
I always ask if I can get payment terms amended to get paid faster (if it’s 30 days, can we make it upon completion? If it’s 60 days, how about 30?). In other cases, I offer a small discount if they pre-pay. 2.5% is my usual pre-payment discount, since they’ll usually use a credit card. So then you have to figure your credit card processing fee via your invoice service (Square is currently 2.75% for invoice, but is soon going up to 2.9% with a nominal per transaction fee). So you’re essentially losing 5.25% but gaining more fluidity. If your margins can absorb that 5%, I think it’s worth to have more flexibility from a cash flow standpoint.
5) Life and work balance
Certainly the lines between life and work are sometimes blurred, so what’s applicable to one should be to other. I would say even more so for those who’ve chosen something creative as work. I like the blurriness; others do not.
And yes, things can be challenging because of those choices. Sometimes very. The dynamics of marriage, kids, social life, etc... well, you get the idea.
So how do I intend to maintain balance between life and work? One way is by establishing a clear daily work schedule starting at 9am and ending somewhere between 5 and 6pm.
I then dedicate days and hours to my various endeavors, while also allowing myself some wiggle room each day because I know my personality and how I’ll rebel if it’s too rigid.
I’ve already edited this schedule a few times since mid-June when I became self-employed, which is great. That’s a conscious and confident decision since I’m understanding what works and doesn’t for me now.
Would you like to see my schedule? If so, I can link to a PDF.
Then there’s also the issue of social activities that are IRL. I could seriously go out each and every night if I wanted / could, typically for dinner, beer, and/or cocktail, but that’s not sustainable. Even if it’s super fun and with a friend who’s a fellow artist, designers, or entrepreneur, it’s still sort of for work. I love these hang outs, and don’t mind that those lines are blurred between friends, fun, and work-related chats, but there’s still balance to maintain between life and work that’s important for a lot of reasons.
The takeaway here is to be honest with yourself about what you want to focus on and why it matters. And, further, how that can dovetail effectively with life / home / family stuff? It’s tough, and the outcome may not be pleasant, but you have to do figure this out.
Also, simple as it may sound, saying ‘no’ or ‘maybe in a few weeks’ is never a bad thing. I have trouble with this sometimes. :D
I’ve distilled what is helping me move forward into four simple things:
Make conscious, confident choices - this is a must
Make art - this is super important, whether a doodle or something big
Do the work - because planning and business development can be super time-consuming and important but it’s not the actual work
Choose happiness - I can be heavy-minded too often lately, and that’s not really me. Being happy is not always an option given how life and brains work, but if you can, choose happiness
I think if I’m successful in the first 3, happiness will be easier to achieve.
How about you? What are the morsels of wisdom and challenges you’ve discovered from working for yourself? Please do share!
