10 Things You'll Learn In Your First Year of Entrepreneurship

Wow.

A year ago today was a big ol’ day. On January 15th 2019, I began Day One of entrepreneurship. It was the day I started my business.

No boss. No employer. No idea how it would
turn out. Nooo idea what I was doing.

Just an idea of what I wanted my life to look like and a few self-taught skills in my back pocket that I thought I could turn into…something.

“Something” is now Hart & Soul Co. and it’s been around for a year and oh-my-word, what a ride it’s been. So many ups, so many downs and so (so so) many lessons.

But I’ve narrowed them down to the the biggest things, the most stand-out things, the most impactful things that I encountered this year, in order to share them with you :)

There were logistical lessons…

…head lessons, if you will. Lessons in the real building blocks of starting a business, of operating with efficiency, of marketing and networking and taxes (gross) and schedules and community and office space.

Then there were emotional lessons…

…heart lessons, if you will. Lessons in fear and doubt and bravery and growth. Messages from society and from within, about everything from my determination (do I have enough of it?) to my self-worth (do I deserve this?).

Everyone’s journey to and through entrepreneurship is different and I’ll say right now, there’s no wrong way to come into it. And while we all learn different things as we start different businesses, I figured — on this momentous occasion of omg-I-built-a-business-that-has-worked-for-a-whole-YEAR — that I’d share a bit of my journey in the realest way I can.

The ups AND the downs.

Because without the former, there’s just no point. And without the latter, you miss out on the beauty of the lessons and the magic of the growth. ♡

Logistical Lessons (From the Head)

Lesson 1: Most of what I learned, I learned by DOING.

I worked in restaurants for many years and the first restaurant job I ever got was at a relatively high-class place. They had high standards for their servers and took their training process very seriously (like, there were daily, detailed quizzes. And they were HARD).

Toward the end of my training, I was “mock serving” one of the managers. I was doing okay, but certainly not perfect. I was nervous and it showed (#performanceanxiety) and I was sure the manager wasn’t going to “pass” me.

But he did. And when I looked surprised, he said, “Look, starting out, some of this is knowledge. But most of it you’re not really going to learn or absorb until you do it for a while.”

I’ve never forgotten that. And I re-learned it all over again during my first year of business ownership.

I knew Squarespace pretty well last January. But I know it INCREDIBLY well this January. I know more about coding, more about customization, more about SEO, more about design elements, more about the psychology of site visitors, more about templates and layouts and text and photos, and the list goes on. And I’ll know it even better by next January.

And I know most of these new things because clients asked me for things I’d never attempted before. But they asked me. So I did my research, implemented new things I found, tweaked them until they worked for me, practiced some more, recorded my findings, and now — I know new things.

And I know them because I just…did them. Such a nice reminder that you're allowed to learn as you go.

Lesson 2: I learned about the importance of a system.

Disclaimer: I’m an organization nerd. I like files. I like folders. I like sorting things. I like it when everything has it’s place. Chaos is not my jam. I do not function well (or at least efficiently) within it, and I LOVE being efficient.

So to me, a system was very, very necessary.

When a client reaches out, what is my next step? When they book with me, what resources will they want from me? What will I want from them and how can I get it? What can I tell clients about their timeline for work with me? What are my on-boarding/off-boarding steps? How can I make all of this seamless and easy for me AND my clients?

I needed these answers. And for the first time in my life, I didn’t have anybody I ask. I had to (gulp) make them up.

But a wise friend once told me, “It’s all about managing expectations.” And to be fair, that’s all I ever really want from a system: a series of consistent, dependable expectations for what’s happening next. So I took these wise words to heart, and I’ll pass the super secret formula on to you:

Step 1: Tell people what you’re going to do.

Step 2: Do it — with timeliness and integrity.

Step 3: Repeat steps 1-2 consistently.

BOOM. SYSTEM. (*inner organization nerd does the happiest of dances*)

(Side note: when coming up with my system, I tried to balance it between what I thought my clients would want and what I want. And I at the end of the day, if I was ever in doubt, I aired on the side of what I would want.

Because I’m more likely to stick to it. Because it’s MY business and I deserve to feel comfortable. Because clients will always work with you within your own framework (and mostly just appreciate that you have one) — especially if you have fabulous clients like I do.

And because you didn’t start your own damn business just to fall in line with someone else’s expectations. Okay? Okay.)

Lesson 3: I learned about the importance of a schedule.

I’m my own boss! I don’t have to punch a clock at 8AM! I don’t have to work until 5PM! I can go to the gym in the middle of the day! I can take a three hour lunch break! FREEDOM!

I lived in that land for a while. But remember when I said I’m an organization nerd? Yeah. I didn’t do well without a schedule for long.

Now don’t get me wrong — my schedule still isn’t super strict. But it turns out I couldn’t just throw my planner out the window because I didn’t have designated hours anymore. In fact, I have never needed a planner more than I did when I became my own boss.

I got a handle on this over the summer when I joined Sarajane Case’s Brave Collective and learned about the magic of bullet journaling. It helped me create time and ways to plan out my days/weeks/months so that I could cultivate business AND personal goals, while also giving me room to reflect on those days/weeks/months that had already passed. It’s been a life-saver. If you need a little guidance in the scheduling zone, I highly recommend giving the Brave Collective a try.

But overall, I learned that despite my penchant for freedom (and relative disdain for being told what to do, whooops), I DID need parameters on my schedule to have a productive and enjoyable work-life balance.

Lesson 4: I learned about the importance of community.

One of the first things I did a year ago when this journey began was take an almost obsessive dive into local resources. I’m based in Asheville, NC — the magical mountain town in which I was raised and can’t manage to leave for longer than a year or two. But even though I grew up here, I had no idea what an incredible entrepreneurial community it had!

The Chamber of Commerce had free “intro into the start-up world” classes. A local foundation called Hatch has monthly “pitch parties” where you can listen to people practice their business pitches and get feedback on your own. The local community college (AB-Tech) has a small business center with tons of free classes on everything from marketing to taxes to registering as a sole proprietorship vs. an LLC. There’s a group called the Young Professionals of Asheville that has social/networking/volunteer events three times a month. Asheville has a chapter of Creative Mornings and 1 Million Cups. It’s an absolute HOT BED of entrepreneurial activity and support. And Asheville certainly isn't the only city like this.

The best part? Through this variety of resources, I’ve met incredible entrepreneurs. And I needed them, because when you’re full of doubt and nerves and overwhelm with this whole “business owner” thing, no one gets you quite like someone who’s been there before.

I may have been “going it alone” professionally, but I wouldn’t be here — a year in and not broke — without the community I’ve met, befriended and gathered throughout the entrepreneurial scene.

(Side note: Networking events not your scene? Try online groups or memberships! I joined Tyler McCall’s Follower To Fan Society and Sarajane’s Brave Collective and have met wonderful, supportive folks through both. Or try a co-working space! Everyone is in their own world, but you can still connect with others when you need/want to.)

Lesson 5: I learned the mantra, “One step at a time.”

One. Step. At. A. Time. My mother has been telling me this for years. How proud she’ll be to know I finally took it to heart over the last 365 days.

This might just be me, but I tend to either have 837247 ideas at once or none at all — but more often than not, it’s the former. And when I have those 837247 ideas, I have a tendency to want to make them all happen RIGHT NOW. And since that's impossible, I become immediately overwhelmed leading to motivational paralysis leading to negative self-talk leading to attempting zero of my 837247 ideas.

I'd call that counterproductive. I'd also call that "welcome to the creative process" and “no, you’re not the only one who does that.”

As a culture, we put so much pressure on ourselves to be so good, so successful, so perfect SO soon. We live in a society that glorifies busy work and shames slow, methodic effort, only coming to recognize people once they’re “great" or they've "made it," forgetting to shine the light all of the steps and all of the time it took them to get there.

Even this post is evidence: only talking about my business once it’s been through a year of relative success instead of talking openly about the struggles within the steps I’ve been taking for the last 365 days. It’s a culture. I’m trying to break out of it.

The difference between now and a year ago isn’t that I have fewer ideas. On the contrary, I have more than ever. But I don’t give in to the desperate panic and inevitable paralysis and resulting self-shame now.

Instead, I remind myself that I can only do a couple of things today. There’s really only so much daylight, and I have a personal life to live as well. And living a good life is the point, the whole entire point, behind why I first jumped into entrepreneurship a year ago.

So if you’ve got dozens, hundreds, thousands of ideas and no clue as to where you should start…start with the first smallest step, and give yourself time. Stay consistent and don’t be too hard on yourself. Take it one step at a time.

Emotional Lessons (From the Heart)

Lesson 6: I learned that feeling clueless is NORMAL.

I’ve heard of people who carefully, strategically plan out their businesses before they leap head first into them. I took the “just dive in and make it work based on impressive faith in yourself and the reality that you have to pay bills” approach, so I wouldn’t know what that’s like, but I’ve heard of it.

I have a theory though.

That no matter how prepared you are (or are not), there will always come the day or situation or client that makes you feel…clueless. Unprepared. Maybe even undeserving (see Lesson #7 for more on that) of calling yourself a business owner.

So I’m here to tell you: it WILL happen. And you won’t be wrong. You will be unprepared. You will be clueless. The only thing you won’t be is abnormal.

So when it happens, instead of panicking or questioning your very self-worth (see Lesson #9 for that one), know that every business owner on earth has been there before, and will likely be there again. Being clueless is part of the process.

Lesson 7: I learned that impostor syndrome is REAL.

“I have written eleven books, but each time I think, ‘Uh oh, they’re going to find out now. I’ve run a game on everybody and they’re going to find me out.’”

You know who said that? About fearing that people would find out she wasn’t a “real” writer?

Maya Angelou.

Impostor syndrome is when — no matter how much experience you have, how smart you are, how accomplished you, how hard you’ve worked — you, somehow, are a fraud who actually has no idea what they’re doing. More so, you think that anytime someone DOES think you’re a true professional wizard in your field, you have simply fooled them into thinking it! You haven’t earned that distinction or your accomplishments — you’ve only tricked people into believing you have. And any moment now they’re going to realize that you’re not really a writer or a web designer or a health coach or a [insert your title here].

That’s impostor syndrome.

I had it. I HAVE it. Impostor syndrome and I duke it out at least a couple times a month (it's also statistically more prevalent among women, so WATCH FOR IT, LADIES). So far the only cure I've found for it is 1) awareness for when it's showing up and 2) reminding myself that my hard work matters.

I know more than I did and I learn more every day, and I put as much of that as possible toward helping other achieve their goals; that matters. My constant desire to learn more and improve; that matters. My skills that I’ve learned and paid for and practiced on my own time; they matter.

I don’t know everything, but I know my trade and I know what I’m doing to the extent that I can (because who can know everything all the time?). And when impostor syndrome shows up, I say hi, let it swirl around for a moment and then send it on it’s way. (But hey, if you have more effective ways of dealing with this, holla at ya girl, because I’m always open to new ways of giving it the boot.)

Lesson 8: I learned that I have a complicated relationship with “the hustle.”

Another disclaimer: I’m still sifting through this one.

But I don’t think I like it. I don’t think I like the concept of “the hustle.”

When I started my business, I started following a variety of “entrepreneur” related Instagram accounts. You know, for inspiration. But far from inspired, every time I scrolled past a “I’ve got a dream that’s worth more than my sleep” or “your lifestyle depends on your work ethic” or “a few years of hustling can produce a lifetime of freedom" post, I would feel…not inspired.

Instead it would bring on bouts of self-judgement and criticism. How foolish, how unworthy I was of success because I chose things like sleep over my “dream” or friends & family over my desired “lifestyle.” How not enough of me.

But…I like my sleep. I think it’s important and I don’t function well without it.

And I think my lifestyle depends on much, much more than my work ethic. (Like my white, cis, female privilege for starters.)

And I don’t think “hustling” and “freedom” have to be mutually exclusive. I work very hard and enjoy freedom (much more than I’ve ever had before) simultaneously, quite often.

Now, it might not be “the hustle” itself I dislike. It’s likely just certain definitions of it or the widely-accepted societal view of it. In all honesty, I might like it just fine — my own definition of it, anyway.

What I don’t like is when “the hustle” seems to glorify burnout. Like if you work so hard, so often that you’re exhausted and have no time to take care of yourself because “you’re in pursuit of your dream,” THEN, and only then, have you “hustled.” Only then are you worthy of sleep or freedom or success.

Just…no.

So “the hustle” and I…we’re still figuring out our definition. We’re sorting through what we want our relationship to be, if we decide to be in a relationship at all. Your relationship with it can be what you will, but if I may preach for a moment, I’ll say:

Burnout is not a marker of success. It should not be a goal. It does not define your worthiness. You will have days where you bust your ass and you will have days where you drag your feet, and you are just as worthy, just as accomplished, just as badass and bold and brave and magnificent on both days.

Create your own definition. Because you don’t always have to buy into the ones you’re being fed. And unfollow those damn Instagram accounts.

Thank you for coming to my TED Talk.

Lesson 9: I learned the importance of self-care and self-talk.

I’m going to put this bluntly: if shit-talking yourself was an Olympic event, I’d have several gold medals on my wall.

Earlier this past year, when business would dip or I wouldn’t have bookings, it wasn’t just my business model that I’d question: I’d question myself. It wasn’t that perhaps I needed to solidify a marketing plan or invest in my SEO or reach out to my connections for possible leads…

…it was that I SUCKED AS A PERSON.

Nothing like tying a little self-worth to your professional endeavors, amiright?

I did this, uninterrupted, for years — it wasn’t something I even took note of until I went to graduate school to get my master’s in counseling. And when it was pointed out to me, I worked to become more compassionate towards myself. I made more space in my head and heart for my imperfections.

And my life became…softer. Less seriousness, more light. Less weight, more joy. Less trying, more being. Less struggle, more acceptance.

And yet, there’s something about starting a new endeavor that has a tendency to arouse instant self-judgement and harsh self-criticism.

Are you good enough? Will you succeed? Why aren’t you learning faster? Why don’t you know everything already? Are you doing this right? Will anyone take you seriously? DO you even deserve to be attempting this? What if you mess up? What if you fail?

Your answers to those questions inside your own head matter so, so, so much more than you realize.

I learned that giving myself a little leeway — a little compassion, a little space, a little softness — made a world of difference in my experience as an entrepreneur. In fact, compassionate self-talk is my ultimate form of self-care. I’m a desperate wreck without it; panicked and anxious and doubtful.

But a little self-acceptance goes a long way for me. And I don’t always manage to have it, but I recognize the importance of it. I recognize how it turns my mindset around. Sometimes it just takes me a while to get there.

And in case you haven't noticed (because I didn't until I finished this blog), Lessons 6-9 are mostly about...not tying your entire self-worth to your business or your work. Because when I did it, my life became a pressure cooker and everything was riding on my work...which, in the grand scheme of things, is only one small element of my life. Not even my most valued one.

It's a lesson I'll be learning for years to come. But every now and then it's nice to remember: My business is part of me...but it is not ALL of me.

Lesson 10: Just start.

“It's a terrible thing, I think, in life to wait until you're ready. I have this feeling now that actually no one is ever ready to do anything. There is almost no such thing as ready. There is only now. And you may as well do it now. Generally speaking, now is as good a time as any.” - Hugh Laurie

Oh, Hugh. So wise. So British. And so correct.

This year -- a year ago today-- I learned that there is no such thing as “ready.” Not ready enough, anyway.

You won't be ready enough to have a flawless system or schedule.

You won’t be ready enough to avoid feeling clueless.

You won't be ready enough to bypass the judgement of others.

You won’t be ready enough to avoid questioning your self-worth at times.

You won’t be ready enough to be perfect right out of the gates.

You won't even be ready enough to avoid failure.

Basically: You won’t be ready enough to outsmart the natural, normal “downs” that accompany the “ups” of starting something new.

There is no level of ready that will allow you to only experience the good days, the kickass days, the ups only, the pros-without-cons. It’s a package deal.

So if you wait until you’re “ready enough” to avoid the “downs”…you’ll never start. And that's the biggest bummer of them all. Because you might fail.

OR.

You might wake up on a Wednesday a year later, make coffee, take your dogs for a walk, and sit in your favorite squishy chair and share a blog about how grateful you are to have learned that you were right 365 days ago: you can do it. You DID it. You’re doing it.

And since Ijeoma Umebinyuo shares this message more poetically than I ever could, I'll let her do it:

“Start now. Start where you are. Start with fear. Start with pain. Start with doubt. Start with hands shaking. Start with voice trembling but start. Start and don’t stop. Start where you are, with what you have. Just... start.”

—

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