They say time flies, but man oh man WHERE DOES IT GO???

At this time last year, I was eagerly kicking off life as a full-time entrepreneur. I’d been doing the whole side-hustle thing for quite some time, but completely leaving my 9-5 job as a Research and Development Engineer so that I could pursue my business full-time was scary AF!

We had also just left our previous apartment, were living out of a hotel (a story for another day lol), house hunting, and overall there was just SO much unknown about me running my own business…

Would my business totally fail?

Would things actually be better than in my old job?

How would I get insurance?

How do you even run a whole entire business?!

So today, as I look back on my first full year as a self-employed business owner/entrepreneur, I’m shedding light on the lessons I’ve learned, the things I definitely don’t miss about my 9-5, and a few surprising things I do miss!

In no particular order…

7 Lessons I’ve learned from a full year of being self-employed

1. There are no rules. 

Seriously, there aren’t. I couldn’t even stretch to guess the number of entrepreneurs I’ve met over this past year and chatted biz with, BUT one thing I can tell you is that we are ALL just flying by the seat of our pants.

Every single person I’ve spoken to that runs their own business is (and always has been) quite literally just figuring it out as they go. You’ll never have all the answers, but nobody does. And anyone who says they do, is a lying liar. You figure it out as you go, and YOU get to create the rules.

2. Getting health insurance as a self employed, single person over the age of 26 in the United States is a PAIN IN THE ASS!

This was one of THE biggest reasons I held onto my 9-5 job for as long as I did, and it was AS stressful as I expected it to be. I had zero clue how to find health insurance, and the options I could find were easily $500+ per month for catastrophic coverage (i.e. expensive as hell for practically no coverage at all).

How could that possibly be the only option?? 

Unfortunately, there is little to no actually helpful information available for self-employed people that need their own insurance, and if you’re like me, most of your friends and family have always had insurance through their employer – so even your go-to advice givers are often helpless on this front. I had many, many sleepless nights wondering what I was going to do for health insurance, because lord knows that even the simplest of unexpected hospital visits in the US would absolutely obliterate my bank account. 

My saving grace was finding a “Healthcare Navigator”. A Healthcare Navigator is someone who helps you, well, navigate your healthcare options including pricing and coverage options. Mine was amazing, and SO helpful (shout-out to Jacquie!!).

You can find a Healthcare Navigator by contacting your local hospital or doctors office and telling them you wish to make an appointment with a Healthcare Navigator to discuss options for self-employed health insurance. 

3. When you CHOOSE who you work with, it can actually be super fun. 

One big lesson I’ve learned this past year is that having a say in who you work with, can make work SO much more fun. In a 9-5, you work with who you work with. When you run your own business, you can literally design your business to serve the types of people you love working with most.

For me, I tailor my business towards passionate, creative women entrepreneurs. These are women who absolutely ADORE what they do, and the fire inside of them is freaking contagious!

How could you not love working with people like that?!

4. Friends and family will support you way more than you think.

Let me start this one out by saying that this may be semi-specific to me, and that I truly feel for people who aren’t encouraged and supported by their family and friends because that totally sucks big time… BUT in my personal experience I have found that friends and family were much more supportive than I originally expected. That’s not to say that I expected them to shit all over my dreams, but I’ve been overwhelmingly surprised with the positive words of encouragement and genuine interest in my business that I’ve received. 

I’m also someone who doesn’t push my business on anyone. A-N-Y-O-N-E. I think this is where many business owners go wrong. I’ve never once tried to solicit a family or friend for my paid business services, and personally I recommend fellow business owners do the same. If friends/family approach me about working together, great! But I will not make an unsolicited pitch about my paid services to them, period.

Family and friends are here to encourage you and be your cheerleaders, not your source of income. If you view it that way, I hope you’ll have an equally as supportive fanbase as I do!

5. Having a flexible work schedule will do wonders for your sanity. 

This was a biggie for me. Not long into working for myself, I began to realize that simply having the flexibility to adjust my schedule as needed (instead of a rigid 8am – 5pm schedule, with lunch at noon) does wonderssss for my sanity and overall happiness.

Things like being able to take the dogs for a midday walk in the woods, being able to shamelessly step away from my work when I can’t focus, working outside in the sun, sleeping in when I need it, and just the overall general ability to bend my days around my needs has been UH-MAZING! Definitely recommend! 

6. Stay in your own lane – stop comparing.

Comparison is the death of all things in the world of entrepreneurship.

I’m just going to say this once… STOP COMPARING YOURSELF TO OTHERS. You don’t know their behind-the-scenes, their sacrifices, their struggles, their life! Your goals aren’t the same as theirs.

Comparing your business to their highlight reel, or your Chapter 1 to their Chapter 10 is the best and quickest way to confidently reassure yourself that you’re nothing but a failure and you’ll never amount to anything.

Spoiler alert: You’re not a failure, and you will do amazing things!

Stay in your own freaking lane, set goals that make YOU excited, and then go crush them! Screw what everyone else is doing; YOU make the rules!

7. Entrepreneurship is a rollercoaster – buckle up.

Ever heard of something called “feast or famine”? It’s essentially saying that you either have way too much of something, or not nearly enough. I’ve definitely found this to be the case with my business. I’m either up to my ears in client projects, websites, and #allthethings… OR I’m twiddling my thumbs wondering where everyone went. 

*insert ‘Come back!’ scene from Titanic* 

This can definitely be really stressful at times when your business is your only source of income.

Sure, the “feast” times feel super awesome and make you feel on top of the world, but the “famine” times can get tough. Bills still need to be paid whether you’re making enough to cover them or not.

It can sometimes feel like a bit of rollercoaster, so having a financial safety net built up is a great idea, and also perhaps a business model that’s conducive to repeat clients (aka. recurring revenue).

Unfortunately for website designers like myself, most people don’t need multiple websites so even if your clients are over-the-moon in love with you, the potential for consistent repeat business isn’t always there. In that case, it’s always a good idea to diversify your income streams and consider some options for passive income or recurring income through other complementary (not complimentary!) services you offer.

A few things I miss about my 9-5:

A consistent, predictable paycheck.

This one might be the thing I miss the most. Like I just mentioned, the feast-or-famine struggle is realllll sometimes, and I think having a consistent, predictable income is definitely something I didn’t fully appreciate when I had it.

There are totally ways to create a consistent, predictable income source as an entrepreneur, it’s just not a guarantee and often requires a bit more effort than with a 9-5 where it’s generally a given.

Coworkers to shoot the shit with.

Working from home (or wherever you want) can be amazing, but it can also get lonely. While most days I’m totally fine with working by myself and chatting with clients via email, some days I miss having the ability to sneak over to my fave coworkers cubicle and gossip about who-knows-what, and even sometimes the comradery of venting about our jobs together lol. Although I suppose it’s quite nice to not hate my job anymore too! 

Benefits such as health insurance & a 401k match.

Mannnn this one makes me sound old, but YUP I’m saying it – I miss my benefits!

I miss not having to spend hours and hours searching for healthcare options that don’t cost an arm and a leg… 
I miss my employer
paying for a portion of my health insurance… 
And I miss literally getting free money put into my retirement plan by my employer…

Apparently I just miss them for their money 😉

Paid time off.

I remember when I would make sure to use up every single vacation day I was given, because I got paid for it anyway so you bet I was gonna use it!

(I was also one of those employees who straight up dropped off the face of the earth while on vacation. Wanna send me an email? Sorry, new phone who dis?)

Having paid vacation time was definitely another thing I took for granted.

Now, when I go on vacation, I pretty much know I’ll earn $0 while I’m away *cue the nervous sweats*.

I also have to make a conscious effort to avoid my email, because I often have those moments of “well I should just check-in in case anyone has an emergency”. For me, I’ve learned that the best way to avoid that is to delete my email app off my phone altogether while on vacation.

But in short, I do miss the days of getting paid while on vacation, and then being able to use that money to pay for the vacation. 

Anyone want to sponsor a hard-working entrepreneurs next vacay? Asking for a friend… 😉

Things I don’t miss from my 9-5:

Having a set schedule everyday.

I would say that this difference is one of my favorite new parts of working for myself, but to be honest ALL of these no-longer-requirements are my favorite!

I think for me, a set schedule just doesn’t work. I do like routine, but I like the ability to adjust it as needed. I’m not a robot, I don’t function the exact same way every single day. So not being forced to work the exact same hours, with the exact same breaks, in the exact same environment every single day has been an amazing improvement!

Having to look busy when my work is done.

Woof… You guys, this might have been the worst part of a 9-5 for me. 

I’m a very efficient worker, and I always hated that even though I got all my work done in a quick, high-quality manner, I still had to sit at my desk until 4pm (I worked 7am – 4pm)… even if I had nothing to do. Like why?! (PS. I was salaried, which makes even less sense)!

If I got allll my work done (and even got ahead on stuff) I still had to be “at work” from 7am – 4pm, Monday through Friday…ugh.

Now, I’m not saying that I want the ability to leave whenever I want… I realize that’s “not how it works”. What I AM saying is that if my job performance is good, I’m a trusted employee that’s completing all my work to a high caliper, and nobody else needs me – there is literally no purpose in making me sit there and look busy. I’m fooling nobody, and I’m resentful inside.

Having to always look busy when I didn’t have enough work to keep me busy (and yes, I asked for more) is definitely something I do not miss at all.

The hassle of running errands and making appointments, when everything closes at 5pm.

In other countries maybe this isn’t the case, but in the US there are SO many businesses that are open strictly from 8am to 5pm. And you know when everyone else works? 8am to 5pm.

Post offices, banks, dentist offices, doctors, you name it… tons of important services you often need, are only open while you’re literally not able to get there.

This means you have to rush to the post office or bank on your lunch break, take a half-day to make a doctors appointment, or otherwise finagle your schedule to make these errands and appointments work.

Sure, people have been doing it for ages and it’s just become the norm to take time-off for appointments or to sprint out the door at lunch time to run errands, but NOT having to do that is suuuuper nice. 

Tallying up my remaining days off.

I know I said that not having to ‘look busy’ was my new fave thing, but I might have lied… Because not having to constantly tally up my remaining days off is SO. FREAKING. NICE. 

I love traveling, and I also don’t live near a lot of my friends and family. Which means that between planning travel trips AND wanting to spend time with friends and family (whether at home or adventuring with them), it was always so hard to find the vacation days to do it all.

“Okay so if we go on vacation from Saturday to the following Sunday, and overlap it with Memorial Day, that’s one less vacation day we need to use. Then we can use that extra vacation day for cousin Kelly’s wedding in June that falls on a Friday”.

Yeah, no… don’t have to do that anymore 🙌 PRAISE BE!

To that point, I was actually able to take an entire weeklong trip to attend two out-of-state friends’ weddings this past September AND a 10 day trip to Colombia AND plentiful half-days on summer Fridays when the sun is shining and ya girl just don’t wanna work anymore! ☀️

Like I said, this miiight be my fave change in running my own business – and it’s as great as I expected it to be! 😍

Annnd that’s a wrap!

It’s safe to say that my first year as a full-time entrepreneur has been a HUGE learning experience, and I don’t expect to stop learning new things everyday anytime soon.

My biggest takeaways are that while the entrepreneurship isn’t for the faint of heart, I’ve also seen a huge shift in my own level of happiness and just overall life-satisfaction.

There are certainly still the days of “was this the right choice? Am I going to fail? Should I go back to my 9-5?”… and from what I’ve heard, those thoughts don’t ever go away, for ANY entrepreneurs. 

But if your reason for starting your own business is strong enough, passion-fueled enough, and you’ve got a helluvah lot of grit in ya – it’s absolutely possible, and absolutely worth it.

Remember – You can’t fail if you never quit.