36 Lessons I Learned from 36 Months Running an Online Business

Has it really been three years!?

HOLY. SHIT. ?

I can’t believe it, but it has.

In April of 2015, my husband and I (we were working at the same place) were let go from our shitty job on the SAME day.

(This happened about a week after I found out I had an early stage skin cancer on my leg. #FunTimes)

Just four months after that, I had built a $5,000/mo freelance writing business.

And now, 3 years later, I run a 6-figure blog/business that allows me to be creative, work from anywhere (which I’ll be taking advantage of VERY soon when I start traveling full-time!) and help others reach their creative entrepreneur goals.

I’ve come a LONG way over the past 3 years. Lots of successful moments, and lots of failures.

So I figured:

Why not share what I’ve learned with you lovely folks?

Let’s talk about some of the most important lessons I’ve learned, and I’ll share some of my best advice for building a business along the way.

Enjoy. ?

36 Lessons I Learned in 36 Months of Running an Online Business

1. Everyone preaching to “slow down” is doing so because they’re already past the hustle phase of their business. 

Once, someone on social media told me that they were tired of hearing my “toxic” message that entrepreneurs need to hustle.

…But I’m going to keep preaching to “hustle” as long as I have newbie entrepreneurs (or anyone with a goal that requires lots of hustle) in my audience.

Because it took a HELL of a lot of hustle for me to get to where I am today. Especially when I first started out.

So then, how, in good conscience, can I tell my audience that hustle is unnecessary?

I’ll let my recent Twitter moment explain a bit more.

2. You’re going to have to work hard and probably long hours when you first start out.

To piggyback off the last point, you need to understand that building a business isn’t easy. Shit isn’t handed to you.

You’re going to have to hustle. Just make sure you put an expiration date on the hustle.

Set a goal and give that goal a timeline.

Then, put in the work so you can enjoy more freedom once you’ve met your goal.

3. You’re going to piss a lot of people off. That’s okay.

Honestly, if you’re not pissing people off, you’re probably not being vulnerable and REAL enough online.

I *constantly* get emails/comments from people who hate my swearing, despise my writing style, don’t like the way I dress or decorate my workspace… the list could go on.

You will never make everyone happy.

Relieve yourself of the need to TRY to make everyone happy, and just focus on being yourself. 

As cheesy as that sounds, it’s the best way for you to be happy with your business while simultaneously attracting an audience who appreciate the REAL you.

4. Master the fundamentals, and success will follow.

Chances are, some “super special morning routine that all successful entrepreneurs swear by” isn’t going to change your career. Neither will a list of “hacks” or “secrets.”

Really, business is all about mastering the fundamentals.

Content marketing. Creating a product or service that solves a specific person’s problem. Building a strong community. Branding. Learning how to SELL.

Focus on the fundamentals and the long game – not some bullshit “trick” you saw in a blog post.

5. You have to be willing to make an ass of yourself.

If you put pressure on yourself to be good at everything from the start, you’ll NEVER take action at all – because NO ONE starts anything as an expert.

Give yourself permission to be a beginner.

Fuck up, and learn from it.

6. Imperfect action is better than fearful stagnation.

I sucked at editing videos, being on camera, and YouTube in general when I first started my channel.

But if you watch my channel now (Jorden Makelle on YouTube!), you see a clear improvement and evolution.

Think about this:

What if I had waited until I felt comfortable to start my channel?

I probably wouldn’t have a channel at all.

…Just. Fucking. Start.

7. Working from home long-term means you have to work extra hard to be healthy – mentally and physically.

It’s SO easy to get lazy about leaving the house when it’s where you live AND work.

When you first start working from home, you’re excited to spend some extra time around your pets. You’re thrilled to be able to avoid rush hour traffic. You’re convinced you could avoid human interaction for years and not give a single, solitary fuck.

Then, 6 months later, you find yourself alternating between the same two pairs of sweatpants, completely drained of all social skills because you only leave the house to get groceries. 

…Yeah.

Solitary confinement isn’t good for your mental or physical health.

(Even if you’re an introvert!)

So, choose to work from a coffee shop or park every once in a while.

Head out to a public gym instead of always doing an at-home workout.

It may seem annoying to have to leave at first, but you’ll be glad you did.

8. It’s easy to lose your voice as your audience/business grows.

A bigger audience means bigger pressure to keep people happy.

But remember – it’s not your job to make *everyone* happy.

Yes, you should be kind to people, but don’t lose your voice trying to please everyone.

For me, it’s been hard to avoid taking on a super “customer service-y” tone when I interact with people online. I mean, I AM technically a customer service person for my own business, so it makes sense.

But let me tell you – I’ve been a HELL of a lot happier since taking the pressure to constantly be a ray of fucking sunshine off myself. You’ll be happier being yourself too.

9. Know your fucking worth if you expect other people to.

Your mindset and belief in yourself matters more than you think.

If you don’t believe you’re worth paying well, your potential clients/customers won’t either.

Be optimistic and confident in yourself, even if you have to fake it at first. 

[clickToTweet tweet=”If you don’t believe you’re worth paying well, your potential clients/customers won’t either.” quote=”If you don’t believe you’re worth paying well, your potential clients/customers won’t either.”]

10. Always, ALWAYS ask yourself, “Why?” 

Why do you want 100,000 Instagram followers?

Is that *really* going to improve your business and/or quality of life?

…Or are you just looking for some external validation?

Be honest with yourself.

Ask yourself why you’re doing what you’re doing, whether it’s getting more social media followers, trying to make more revenue, or something else.

There are a lot of business owners out there with 100K social followers who are barely making any money. And a lot of business owners who have crazy revenue numbers, but take home as much money as a call center employee.

Don’t get caught up pursuing a goal just for the sake of pursuing it.

11. Sometimes, it’s smart to quit.

It’s easy to keep doing something that’s working.

But if that thing isn’t making you feel happy and fulfilled, maybe it’s time to quit.

I had to quit freelance writing gradually as my blog/YouTube channel grew because, although I love writing, I knew I wanted more.

I wanted to build a community, create my own products, and have greater freedom in my career.

I definitely took a hit to my income when I cut back on my client work, but it has paid off, because now, I make more than I ever did with client work – and I enjoy what I do a LOT more. I feel like I get to make a bigger positive impact on others, and I’m able to take care of myself better.

Quitting something isn’t always a loss, even if it feels that way at first.

Don’t hold on just because it’s comfortable.

12. If you use other people as your excuse to fail, you’ve already lost.

“But she is so good-looking!”

“But he has a degree from Harvard!”

“Must be nice to have all those connections that I DON’T have.”

It’s easy to come up with reasons why other people are successful and you aren’t.

But the truth is, if you believe in yourself, master the fundamentals in your industry, and put in the work, you can become successful too.

On the other hand, if you think you CAN’T do it – you’re right.

13. Just because everyone else is doing it doesn’t mean it’s right for you.

When everyone closed their Facebook groups, I kept mine open.

When everyone talked about “scaling” and “hiring a team,” I decided to keep my business small and manageable (because, to me, more freedom/less stress is more important than making 1 million dollars per year).

When everyone is waking up at 5AM for their ~*super neat-o morning routine*~ (lol), I’ll be sleeping until at least 8:30AM.

Just because someone tells you something worked for them doesn’t mean it’s the right thing for YOU.

Once you learn the fundamentals of starting and building a business, be confident enough to make your own decisions and trust your intuition.

14. Entrepreneurs are all a little fucked up.

We really are. Otherwise, we wouldn’t willingly choose to work our asses off, make so many sacrifices, and put ourselves out there at the cost of being bashed/rejected non-stop.

Take comfort in the fact that you’re not the only one struggling.

I personally have struggled with anxiety for pretty much my entire life, and I even had a depressive episode earlier this year, which I talked about in a recent YouTube video. #FunTimes

No one has their shit together as much as you think they do.

You’re not alone.

15. Building community is everything.

Building a community means creating a mutually beneficial relationship.

You have something to offer your community, and they support you (maybe by sharing your content, spreading the word about your business, or even working with you).

Stop focusing on vanity metrics on social media, and go deep instead. CARE about your community.

Quality is SO much more important than quantity.

My free Facebook community, Writing Revolters, means SO much to me and I looooove that we’ve been able to create such a positive space there! 

16. …But so is your mental health, so kick people out if you need to. 

Once, someone came into my Facebook community after I’d seen them bashing me elsewhere online.

(This wasn’t them objectively saying they didn’t like something I did or constructively criticizing me – they were straight-up bashing me and lying about me/my business.)

Honestly, this hurt, because this was someone whose name I recognized – someone I had given free business advice to early in my career.

So I kicked them out of the community. Because I can’t feel happy about showing up in my community when I see that person in there every day.

Taking care of yourself is the best way to take care of your community.

…Even if that means removing some people.

Let me be clear:

This does *NOT* mean to banish anyone who disagrees with you.

But don’t make space for trolls and haters in your community either.

What you allow is what you will make space for more of.

17. All entrepreneurs can benefit from therapy.

…And all people in general, really.

I highly recommend finding a good therapist.

It took an unexpected depressive episode to push me into finally going, and I wish I would have done it WAY sooner.

18. You can change anything at any time.

I started my business as a full-time freelance writer, but even at the beginning, I knew it wouldn’t be my long-term career.

I wanted a community. I wanted to create my own products.

So around February 2016, I went ALL IN on my blog. I dedicated hours and hours every day to growing it.

I answered every email in my inbox. Even when it was overwhelming.

I wrote like crazy.  And I hustled my ass off to promote my blog posts.

I won’t sugar coat it:

This was one of the most difficult and demanding phases of my business.

I was essentially running one business full-time while trying to grow a whole other full-time business.

But I knew I had to go through this to make the change I wanted.

If you’re not happy with where you are in your career right now – whether you’re working a 9-to-5 or you have a business that isn’t as fulfilling as you’d like – remember:

You have the power to change your path at any time.

You don’t have to make a massive change overnight (my business transition took almost a year) – you just have to take the first step in the right direction.

19. Starting over is tough, but worth it.

Since I just told you that changing my business from selling services to selling products was one of the most difficult things I’ve done, you may be wondering if I’d do it all over again.

The answer is…

Hell yes I would.

With no hesitation.

Not because I’m a masochist.

But because, in business, a hustle phase is necessary. You just have to make sure you give it an expiration date.

I hustled my ass off to transition from freelancing to selling products because I KNEW I wouldn’t have to hustle forever. I knew it would pay off, and I could eventually slow down when I started making enough passive income.

If you don’t like where you’re at right now, start over. 

20. Bitching online costs you money.

Do you know what 30 minutes of bitching (in a Facebook group, on Reddit, etc.) accomplishes?

Absolutely fucking nothing.

In fact, bitching online COSTS you time, which costs you money in your business.

…Because you could have spent that time creating content, pitching, networking, etc.

Same thing goes for righting people’s wrongs online.

For example, wasting 30 minutes writing some potential client a long-winded email about how their lowball offer devalues you as a writer and the writing community as a whole.

You’re not going to change those people’s minds. It sucks, yes, but you’re just wasting your time. Trust me.

Stop bitching, and be a business owner.

Time is money.

21. Ditch social media and email if you need to.

Hiring someone to manage my email inbox has seriously been one of THE best things I’ve ever done for my mental health.

Now, I still hop in there pretty frequently to check in and respond on occasion, but mostly, my VA handles it.

Since I sometimes get dozens of emails per day across multiple inboxes, this is a HUGE stress reliever.

I still manage my own social media accounts, but I delete the apps from my phone when it starts to feel too heavy.

You probably don’t need social media as much as you think you do.

What you DO need is for your mental health and creativity to remain in tact.

Take a break for a little while if necessary. Don’t worry, the world will keep on movin’.

22. Your work ethic needs to align with your goals.

Do you want to get 1 million YouTube subscribers in the next 12 months and eventually become the next big YouTube star?

Then be prepared to work your ass off and make a lot of sacrifices.

On the other hand, if you want to make $1,000 from your freelance business total over the next 12 months, you probably won’t have to make nearly as many sacrifices.

Sure, it might still be difficult if you’re totally new to online business, but it’s gonna be a hell of a lot more manageable.

My point:

If you have a huge goal, by all means, go for it – but be realistic, and understand that you’re going to have to work harder than most people are willing to work.

If your work ethic doesn’t align with your goal, you’re doomed from the start.

23. Your business is not more important than your loved ones.

This goes back to the point I made earlier about asking yourself, “Why am I doing this?”

It’s easy to get caught up in goals, making money, and growth. And those things aren’t inherently bad, but they can definitely be negative when you don’t know when to stop and/or take a break.

Remember, you started a business to be happier.

But not all rich people are happy. Not all people on the Forbes list are happy. Chasing external validation and moo-lah will leave you feeling empty.

From what I’ve seen, people who have their priorities straight are the happiest.

And your loved ones should be at the top of your priority list.

24. EVERYONE should build passive income streams. 

When my step-dad passed away suddenly last year, I took WEEKS off of work completely to take care of my family, help with the funeral, and grieve.

If I had been working a 9-to-5, this would have been impossible.

If I had a full load of client work, I maaaaaybe could’ve done it, but I would have struggled to pay my bills as a result since client work means trading time for money.

Build passive income streams to create TRUE freedom with your business. 

Start now.

Even if you have to start small. Even if it’s just planning a blog content marketing strategy that’ll allow you to make passive income a year from now.

Because just $1,000 in passive income could make a HUGE difference in your life one day.

25. Self-care isn’t a fucking bath bomb.

Don’t get me wrong. I LOVE a good bath bomb.

But…

Self-care isn’t as simple as being relaxed in colorful bath water for 30 minutes and then spending the other 99% of your life stressed out.

Self-care is a lifestyle overhaul.

It’s talking to yourself the way you’d talk to someone you love.

It’s forgiving yourself when you fail or fuck something up.

It’s exercising and eating healthy most of the time, but happily indulging in junk food and laying on the couch all day every once in a while too.

It’s pushing yourself hard toward the life you want, but not pushing yourself so hard that you have a mental breakdown.

It’s finding BALANCE.

Prioritizing self-care is one of the best things I’ve ever done. For my business and for my life in general.

A bath bomb will make you feel better for a little while, but make sure you’re addressing the root of your problems too – not just throwing a fragrant, fizzy band-aid over them.

26. The shittiest points in life can be the biggest turning points.

I’ll let this Tweet explain:

27. It’s lack of GUTS – not lack of skills, experience, or smarts – that stops most people from becoming successful. 

Think about your biggest goal/dream right now. And ask yourself:

What’s stopping me from achieving this?

Chances are, you’ll trace the reason to fear if you’re honest with yourself.

Fear of failure.

Fear of investing time/money in something without guarantee that it’ll work.

Fear of being judged.

Let me tell you:

There is someone else out there right now who is LESS QUALIFIED than you to achieve your goal – but they’re out there achieving it anyway because they aren’t letting fear stop them.

(While you’re sitting around “thinking about doing it.”)

Don’t let fear hold you back.

Feel the fear, and take bold action anyway.

You’d be surprised what you can accomplish if you just TRY.

Where there’s a will, there’s a way.

28. When you’re setting a big-picture goal, don’t JUST think about the goal – ask yourself what you want your day-to-day life to look like.

For a little while, I thought:

“I really want to be a YouTuber.”

So, I started to execute on that goal. I put out two videos per week. Mostly talking-head style, business-y stuff.

And then I realized something:

While the goal sounded nice, I was NOT enjoying the day-to-day tasks associated with going “all in” on YouTube as a business vlogger.

So, I got bored and burnt out. Fast.

This happens a lot with creatives.

We get so caught up in an exciting goal that we forget the actual WORK it takes to get there.

There are a lot of things I want to do, for example, I want to write a book at some point in my career.

But the timing isn’t right for me right now.

I know this because I don’t currently want my day-to-day life to look like the life of someone who is writing a book.

The extra time spent working every day. The overwhelm. The process itself.

It’s just not for me right now. I think I’ll get back into YouTube one day, and I’m going to write a book one day too.

But until I can get excited about what my day-to-day life will look like pursuing either of those things, it ain’t happenin’.

 

29. Aim for a high-profit business rather than a high-revenue/low-profit business.

Would you rather run a business where:

– You do 3 million in revenue and you’re “internet famous,” but your take-home is $50,000, and you’re extremely stressed out all of the time.

– You do $200,000 in revenue. and your take-home is $125,000. You’re not super well-known (the Forbes list won’t be calling anytime soon…), but you take vacations, work 4-6 hours per day, and generally enjoy what you do.

This seems SO. DAMN. OBVIOUS.

But the sad truth is, many entrepreneurs are picking option 1.

Either that, or they need the external validation that comes with having a massive/famous business. (No judgment here, btw. I fuck up too and have PLENTY of my own issues.)

Don’t make this mistake.

Figure out YOUR values. YOUR goals. What’s important to YOU.

And then build a business based on those things… not on some random dollar amount, internet fame, or getting on an overhyped bullshit business list. 

30. Not all advice is valuable.

Also known as:

“Free advice is worth every penny.”

…When you ask for advice online, there is no guarantee that advice is going to actually be valuable.

Especially if it’s free advice from a stranger who doesn’t know you or anything about your business.

Think about it.

If you go into a community of beginner bloggers asking how you should monetize your blog, you are probably going to be getting advice from people who have not successfully monetized yet.

I see this happen a lot in Facebook groups (and CRINGE when someone responds with “Use Adsense! I made $3.00 last month!”).

If you want REAL business advice, get it from someone who has already successfully done what you’re trying to accomplish.

(And pay them for their advice instead of asking to “pick their brain!”)

31. Exercise every day. It’s good for your mental/physical health, and you’ll get some of your best ideas.

Most of my best business ideas come to me when I’m running or biking.

And, you know, the whole GETTING FIT AS FUCK thing is pretty nice too.

*flexes abs and pulls 20 crop tops out of back of closet*

I have lost about 25 pounds over the past couple years thanks to my regular workouts (and vegan diet – but that’s a blog post for another day), and I ALWAYS feel more creative and mentally healthy when I prioritize regular exercise.

I know it sucks at first, and it’s hard to get motivated. But trust me – the hardest part is actually getting off your ass to GO to the gym. Not the workout itself.

(Pro tip: Invest in a gym membership if you struggle to get motivated. When you pay for something, you’re more likely to use it and make it a priority.)

32. Remember, your business isn’t worth putting yourself in the hospital for.

I’ve read so many horror stories of business owners who ended up suffering MAJOR health problems because of their business.

Listen, y’all. STRESS DOES NOT FUCK AROUND.

Seriously – it can lead to all kinds of health problems. So, don’t put yourself under an immense amount of stress when your body is CLEARLY telling you to stop.

When you DO need to take care of a stressful task, make sure you balance that time with deep breathing, *intentional* breaks (no social media scrolling or email checking!), yoga, etc.

33. You don’t owe people an explanation.

Your parents think starting a business is a stupid idea?

Well… So fucking what?

Last time I checked, it was YOUR life. Not theirs.

This doesn’t just apply to family/friends, though.

It can apply to people who consume your content too, like all of the people on YouTube who don’t like the fact that I swear.

Imagine if I wasted time explaining myself to people who don’t appreciate my swearing and family members who don’t like the way I live my life.

I’d not only be SUPER stressed out – I’d be so busy that I’d barely have any time left to run my business.

Don’t waste your time.

Focus on your goals, not other people’s opinions of you.

34. If you don’t have haters, you’re not putting yourself out there as much as your should be.

Creating content that looks/sounds like everyone else’s will get you a big ol’ lukewarm audience.

…People who just feel “meh” about you.

Do you think those people will ever become your clients/customers?

Nope.

Put your REAL self out there to attract people who are passionate about your content and brand.

Yes, you’ll get some haters in the process, but who cares?

35. If you never get rejected, you’re not trying hard enough.

The first day I sent out cold email pitches as a freelance writer, I got rejected 15 times.

15. Freaking. Times.

But guess what else happened?

I landed two clients.

That’s right. 2 out of 17 pitches resulted in clients.

This would never have happened if I had let fear hold me back.

…Just like another big opportunity I pitched last year to work with a New York Times Bestselling Author’s business.

This honestly felt WAY out of my league, but I pushed through those feelings and pitched myself anyway.

And I landed the opportunity.

Stop letting fear hold you back.

If you’re scared, ask yourself, “What’s the worst thing that could happen if I do this?”

36. No one has their shit together as much as you think they do. 

Confession:

I’m pretty much a high-functioning hot mess.

I constantly feel like I have no clue what I’m doing, even though I’ve been running a business for over three years now.

And I don’t think that feeling will ever go away.

But the truth is, feeling clueless is just part of being an entrepreneur.

You feel the fear and take action anyway.

You remind yourself that you’re human, and that no one has it all figured out.

And you forgive yourself for your shortcomings, focusing instead on what you can offer the world.

—-

I hope you enjoyed this peek into what I’ve learned in 3 years of running an online business! If you did, I would so, SO appreciate if you shared the post on social media.

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