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IN: GirlBossing, Lifestyle

10 Lessons From 5 Years of Entrepreneurship

March 10, 2023 By Melanie 1 Comment

Entrepreneurship lessons as a full time wellness content creator

This month marks five years since I left the corporate marketing world and my position as a digital strategist in favor of being a full time content creator. And wow, the world of entrepreneurship has been quite a journey! What started as nothing more than a fun “side hustle” has transformed into a multi-six figure business. Something that my younger self, the girl who grew up without wealth and worked several retail jobs through college, could never have imagined was possible.

Today, I’m sharing some of the biggest lessons I’ve learned over the course of these last five years. From dealing with loneliness, imposter syndrome, and creative burnouts, to the joys of hiring a team, dream partnerships, beautiful friendships and connecting with over 150K people across multiple platforms.

I know many of you have also chosen a non-traditional career path and I hope by sharing my struggles, successes and learnings, you’ll feel inspired to continue on your own journey. If you trust in yourself and put in the work, I promise you there is nothing you can’t accomplish. So grab yourself a cup of coffee and pull up a chair… this is going to be a long one but I’m excited to be sharing these 10 lessons with you.

10 lessons from 5 years of entrepreneurship as a full time content creator

There Will Be Many Highs and Lows

The beauty of entrepreneurship is that all the feelings of success are amplified because you’re the one responsible. This of course is a double edged sword, because the failures and mistakes made are also felt with an increased intensity since there is no one to blame other than yourself. You’ll learn over time how to navigate the rollercoaster of emotions that come with being your own boss but it’s so important to treat yourself with grace and compassion. When the failures happen, as they do for all of us, it’s crucial to treat them as learning opportunities and not allow yourself to wallow in the lows for too long. And when there are high points, celebrate them! Your accomplishments do matter and even though there may not be a promotion track or annual review, I encourage you to find ways to keep track of your “wins” and use them as motivation  to continue on your path.

Diversify Your Streams of Income

There’s an old adage that says “don’t put all your eggs in one basket” and this couldn’t ring more true when you’re an entrepreneur. As a content creator, this means that I should never be relying solely on one source, like brand partnerships, to bring in revenue. My current breakdown of income streams by percentage looks something like this:

  • 80% Partnerships (contracted campaigns with brands)
  • 10% Affiliate Programs (Amazon Storefront, LTK, etc.)
  • 5% Creator Bonuses (Instagram, Pinterest, TikTok creator programs)
  • 3% Product Development (Mindful Morning Planner)
  • 2% Other (Yoga teaching, events, etc.)

In order to diversify my streams of income into what you see above, this required me to diversify my own offerings.  For example, you can find me online via this website, e-newsletter, Facebook group, Like To Know It, Pinterest, TikTok and Instagram. This brings my total “following” to over 150K people, something that I can use to my advantage when negotiating brand campaigns. Outside of the digital space, I’m a certified yoga teacher so I can get hired for specific events and I also started my own women’s community group, Denver Fit Friends, which allows me to  host fitness meetups throughout the year.

Even though your business may look very different from  mine, I encourage you to find your own ways to establish multiple income streams and opportunities.

Recognize Signs of Burnout  Before It Happens

Since entrepreneurship allows you the flexibility to create your own hours it can be super easy to find yourself working around the clock. Figuring out how to simultaneously hustle and ride a wave of inspiration while also establishing boundaries around your work/life balance is probably the trickiest thing about having your own business. It has definitely gotten easier over the years and I often feel like I’m in a really good rhythm with what I do. I’ve become very accustomed to certain months or quarters being busier than others pending brand budgets and activations. For example, Q1 (beginning of year) is notoriously slow while Q4 (holiday season) is always the busiest.

On the other hand, the problem with working random hours, weekends, early mornings and sometimes late at night is that you can push yourself to the point of burnout. This is something I usually experience several times a year, mostly from a creative perspective and other times from simply not slowing down when I notice the initial signs. Since content creation comes more easily  to me than it used to, it means that I can find myself “creating” at some level from the second I get up to the minute I go to bed, every day. Like many jobs in the social media space, being an entrepreneur can feel like an “always on” position and I’ve learned time and time again that boundaries and true days off are the only ways to avoid burning out. 

Know Your Worth and Stick To It

When it comes to managing your own business, really knowing what your product (and time!) is worth financially and sticking to that number can be super challenging. At the end of the day, business is business and when opportunities come your way it can be really hard to turn them down, even if you know from experience that they are lowballing you.

I’m a firm believer that when one door closes, another one will open and I’ve seen this happen time and time again. By sticking to my worth as a content creator, I’m setting expectations for how that agency or brand will work with me in the future. I used to be really worried about offending people or super scared that if I came in too high they would just find someone else. However the more I trusted my instinct and stood firm in my rates and offers, it became abundantly clear that it truly is “just business” and rejecting something because it doesn’t match my rate simply opens up my calendar for another opportunity that will.

This also means being super selective in the offers that I take on. The money might be fantastic short term but if it doesn’t match my business’s core values then it will only hurt in the long run.

Your Work Environment Matters

I recently shared my home office makeover with you all and why it was important to me. When you work from home, finding motivation and a good work flow can be terribly challenging. Being your own boss means you dictate your own hours, oversee your output, establish your own goals and determine how productive you need to be in order to meet your deadlines. Having an established home office space, even if it started as just a small desk shoved in the corner of my 1 bedroom/1 bath NYC apartment, plays such a huge role in my productivity and motivation. Working from the couch or bed can be tempting but I promise that having a separate “work” zone will do wonders for your mental health and overall happiness when working alone.

Lessons learned from entrepreneurship

Learn How To Delegate and Scale Your Business

When it comes to scaling your business, you will eventually have to delegate tasks so that you can focus on your strengths. Learning how to hire and build a team can be one of the toughest things you learn as an entrepreneur but I promise that when you make those right investments your business will reap the rewards.

In 2020 I made the decision to hire a part time marketing assistant who I pay an hourly rate for 10 hours a week. She has now worked with me for 3 years and has played such a huge role in leveling up my offerings and overall brand. By delegating a lot of my graphic design, account & community management and admin tasks to her, I’m able to focus more of my attention on my organic content, brand partnerships, business strategy and community offerings.

In 2022, I joined the IkonicFox Talent Agency in order to have management representation. Having a manager can feel like a huge risk, especially when they take 20% of your partnership earnings and are responsible for communicating with other brands/agencies on your behalf. I was super nervous about it initially but it’s been one of the best business decisions I’ve ever made. They have removed the weight off my shoulders when it comes to negotiating rates, analyzing contracts, tracking payments and establishing a streamlined workflow. Not to mention it makes tax season a whole lot easier.

Find Your Own “Colleagues” and Don’t Be Afraid To Lean On Them

The first few months after venturing into entrepreneurship felt like some of the loneliest months of my life. And truthfully, as an extroverted person, I still struggle all the time with loneliness. I wish I could say you get used to it but the truth is, you never really do.

What has helped me immensely and why many times I miss NYC is because I was able to create so many friendships with other women who are also content creators or within a creative industry. There was a time when I was going to 5-8 “influencer events” a week and I look back on that time with so much fondness because I met some very dear friends at those events.

Surrounding myself with other inspiring women helped get me through some of my deepest bouts of loneliness and entrepreneurial struggles. From co-hosting events and creating content together to supporting each other’s ideas and answering questions, the people I’ve met and friendships I’ve made along the way have been invaluable. And it goes to show that even if you work for yourself, you can still create a large network of “colleagues” to be there beside you through the ups and downs. 

If you’re also struggling with loneliness and isolation as an entrepreneur, I encourage you to seek out your “people.” Find networking events in your area or if there aren’t any, start them yourself! Connect with fellow entrepreneurs through Facebook community groups or privately through DMs on social media. Putting yourself out there is hard but I promise it’ll be worth it.

Give Yourself Goals but Be Flexible

When you’re thinking of venturing into the world of entrepreneurship, some kind of business plan is necessary. It doesn’t always have to be a full-scale 5 year plan but it’s very important to set your sights on specific goals that you’re looking to hit and create a strategy around those goals. Create a process for checking in on the progress you’re making so you can adjust your strategy and output accordingly.

As a content creator, it’s been so important to maintain flexibility with my business goals because the influencer marketing landscape is continuously evolving! When new social media platforms debut (like TikTok’s rise in popularity in 2020) or changes to current platforms are made (like Instagram’s ongoing algorithm shifts) it’s paramount that I learn how to adapt and shift my micro-goals accordingly.

Every industry is so different and perhaps this particular learning is more significant for full-time content creators like myself. But I do believe, no matter what your business is, having a flexible and adaptable business model can be super helpful when you’re an entrepreneur.

Most People Won’t Understand What You Do

Like many entrepreneurs with a non-traditional career path, I still find that most of my family and friends don’t have an understanding of what I do. As influencer marketing has continued to expand, there’s at least a bit more familiarity around content creation than when I first took it full time 5 years ago. However, the number of times people have left comments on my posts or even suggested to my face that I’m bankrolled by my husband or don’t have a “real job” is very unnerving.

I’m not going to lie, this used to really bother me. But as time has gone by, I realized that seeking validation from others will get me nowhere and even if people don’t understand the ins and outs of my business, the ones who matter will at least respect it.

Perhaps the most valuable lesson I learned from trying to explain a non-traditional job to others is that you truly set the standard for how people react. When you speak about your career with respect and passion, most people will reciprocate that response even if they don’t understand it. It’s also crucial to remember that people-pleasing has no place in your business and you don’t need to make people like or understand what you do.

Never Stop Investing In Yourself

No matter what your business is, the only way you can get better at what you do is through practice and some kind of continued education.

Social media is ever changing and as a content creator it’s my job to adapt and adapt quickly. Since taking my business full time 5 years ago the landscape of influencer marketing has changed drastically. On the downside, it’s incredibly saturated and increasingly difficult to stay relevant. On the positive side, the budget brands have dedicated for influencers has gone through the roof since back when I first started my blog.

This makes continuous learning and finding ways to invest in myself and my craft SO important. In 2017 I got my yoga teacher certification just 8 months before I decided to take H&H full time. Since then, I’ve watched countless YouTube tutorials and attended workshops on the ins and outs of content creation. And currently, I decided to enroll in a holistic nutritionist program so I can get a deeper understanding of how nutrition plays a role in our overall health and well-being. 

Whether you decide to hire a business coach, attend workshops, or further your education, investing in yourself will always pay off.

Entrepreneurship Lessons

As I wrap up this blog post, I just want to say thank you so much for being here. Whether you’re new to my page or have been here since my “melyoga1” Instagram days, your support means the world to me. My only hope is that my little corner of the internet has brought you something of value or added a tiny bit of joy to your days.

Truthfully, I have no idea what the next 5 years will bring and that’s okay. In the meantime, I’m grateful to take things day-by-day and am grateful to be sharing it with you.

Filed Under: GirlBossing, Lifestyle

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  1. MAYA says

    March 12, 2023 at 2:46 pm

    LOVE YOUR CONTENT. GREAT POST 🙂

    Reply

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Meet Melanie

Meet Melanie

Hi and welcome to Headstands & Heels! I’m Melanie — a Digital Strategist turned Wellness Entrepreneur, certified yoga instructor (RYT 200), dog mama, and content creator based in Denver. I hope to encourage others to follow their dreams and cultivate a healthy, balanced lifestyle filled with mindfulness and positivity. 💕 Send me a note at: mel@headstandsandheels.com

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One grand weekend to bid farewell to summer☀️⛵️ {📍Grand Lake, CO}

Throwing it back to the #erastour because I’m ju
Throwing it back to the #erastour because I’m just like every other basic B #swiftie who is sooo excited for TS12! 🥰🎶

Anyone else hoping “The Life of a Showgirl” is a full on girly pop album? 🤞🏼 

Sidenote this may have been my favorite outfit everrr and I need to come up with an excuse to wear it again ✨💖

#ts12 #romanticizeyourlife #summerconcert #summervibes #loverera #taylorswiftnation

Life with a little bestie >> 💕✨

#motherhoodi
Life with a little bestie >> 💕✨

#motherhoodismagic #newmomlife #girlmom


Celebrating 8 months with our little bundle of joy
Celebrating 8 months with our little bundle of joy and I can hardly believe how fast the time is flying ✨🎀

This time two years ago I said goodbye to our first baby at 11 weeks pregnant and I’ll never forget the kindness so many of you showed me. I still have many of your messages saved and thinking of them still brings me to tears 💛

If you are currently in the thick of fertility struggles, waiting, hoping and praying for your time — I see you and hope this gives you something beautiful to look forward to. Thank you for being part of my journey and I’m sending all the love your way 💫

My only goal this summer was to take notice of all
My only goal this summer was to take notice of all the little things that spark joy and do them as often as possible 💫

{soft living, wellness, new motherhood, happy habits, mindfulness, cozy hobbies, be present, Pinterest aesthetic, summer vibes, mood board, wellbeing}

We all know making time for hobbies is a healthy h
We all know making time for hobbies is a healthy habit that we can do more of. So if you’re wanting to make more time for yourself but not sure which hobby is right for you, this guide is for you!

✨These 36 hobbies split across 6 categories are PERFECT for your 30s but can also be enjoyed at any age and are meant to help you discover new activities or reconnect with childhood favorites✨

PHYSICAL 
get you moving, support your health, release stress and give you a boost of endorphins

INTELLECTUAL
keep your mind sharp, expand your perspective and help you follow your curiosity 

CREATIVE
allow you to express yourself, tap into playfulness, relax and unwind 

OUTDOORSY
immerse you in fresh air, bring you scenic sights and foster your spirit of adventure 

SPIRITUAL
nourishment your inner world, allow you to feel grounded, connected and more present 

COMMUNITY FOCUSED 
provide a sense of belonging, foster connection, deepen relationships and encourage collaboration
 
Be sure to swipe through the list and SAVE for later! Let me know which ones you’ll be trying more of 💕

This is your sign to consolidate all of your arts
This is your sign to consolidate all of your arts & crafts into a little cozy hobby cart! ✨💛

My random art supplies have been scattered about in various rooms & closets in my home so I FINALLY got around to organizing them 🎨 

From scrapbooking, to coloring books, painting, and decoupage tools — these cozy crafts are now easily accessible and hopefully will make finding the time for creative hobbies to be a tad bit easier ☺️

Let me know if you’re also in your cozy hobby era! And let me know which hobby you want to make more time for 👇🏼

One of my goals is to make my evening routines scr
One of my goals is to make my evening routines screen free and as cozy as possible ✨💫

Last night, that looked like an everything shower, a hydrating face mask in my fluffy new strawberry robe, a hot cup of peppermint tea and watercolors in bed. Literally couldn’t think of a more perfect, relaxing way to unwind 

I finally organized all of my craft items into a little hobby cart that I’ll be sharing with you all tomorrow! And I hope to give you some ideas on how to slow down and make the most of the time you have for yourself because we all deserve a little coziness and self care ✨💫

#romanticizeyourlife #eveningroutine #eveningdiaries #selfcarediaries

My goal is to make my evening routines feel a litt
My goal is to make my evening routines feel a little more special this season with lots of self care and cozy hobbies ✨💛 

Last night, that looked like an everything shower, a hydrating face mask in my fluffy new strawberry robe, a hot cup of peppermint tea and watercolors in bed. Literally couldn’t think of a more perfect, relaxing way to unwind 

I finally organized all of my craft items into a little hobby cart that I’ll be sharing with you all tomorrow! And I hope to give you some ideas on how to slow down and make the most of the time you have for yourself because we all deserve a little coziness and self care ✨💫

#romanticizeyourlife #eveningroutine #eveningdiaries #selfcarediaries

I know so many people are already posting about Fa
I know so many people are already posting about Fall but am I the only one who is happy we still have a few more weeks of summer? ☀️ 

Since we have some time before we switch to cozy drinks, this #matchamonday is starring one of my absolute favorite combos… an iced mango matcha latte 🥭🍵

The sweet & earthy flavors work sooo well together, not to mention the layers are super pretty! 

Here’s your sign to make one

All you need is: 

✨ 1 tsp ceremonial grade matcha mixed with 1/4 cup hot water 
✨ 1 cup your choice of milk 
✨ 1/2 ripe mango mashed

Whisk the matcha and hot (not boiling) water and set aside. Mash ripe mango and add to glass. Top with ice, milk and matcha! 💛

Let me know if you’ll be making this and if you’re currently hanging onto summer vibes or leaning into early Autumn

For all the women in your 30s — cheers to trying
For all the women in your 30s — cheers to trying new and old hobbies, connecting to your inner child, fully embracing all the things you love and feeling so much more confident in who you are 💕💫 

#romanticizeyourlife #lifeinyour30s 
#joyfulliving #smalljoys #cozyhobbies

Happy Monday! Here’s a gentle reminder that your
Happy Monday! Here’s a gentle reminder that your morning routine doesn’t have to take long for it to be impactful. Adding little moments of mindfulness can do wonders for your physical and emotional wellbeing and even 5 minutes of self-care can set the tone for the day 🦋💕

Since my mornings are a bit more chaotic now, following my 3 step formula to nourish, move, and practice self care has been SO helpful during this phase of life 💫. And I hope it does the same for you! 

Swipe through for some mindful exercises that take less than 5 minutes and comment WORKSHEET if you’d like to receive my free, printable Mindful Morning worksheet straight to your inbox 

Here’s to making our morning routine feel a little more special, even on those extra busy days ✨

#healthylifestyle #healthyhabits #romanticizeyourlife #happyandhealthylife #joyfulliving #softwellness


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Currently Pinning

  • pumpkin patch, fall aesthetic, autumn vibes
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  • A cheerful garland made of felt hearts in shades of red, pink, and white. The hearts are strung on a jute twine and draped across a mantel, adding festive flair to the room.  ​  ​Why They Sell:  ​Garlands are versatile decorations for homes, offices, or parties, and they’re lightweight and easy to ship, making them perfect for online sales.
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One grand weekend to bid farewell to summer☀️⛵️ {📍Grand Lake, CO}
Throwing it back to the #erastour because I’m ju Throwing it back to the #erastour because I’m just like every other basic B #swiftie who is sooo excited for TS12! 🥰🎶

Anyone else hoping “The Life of a Showgirl” is a full on girly pop album? 🤞🏼 

Sidenote this may have been my favorite outfit everrr and I need to come up with an excuse to wear it again ✨💖

#ts12 #romanticizeyourlife #summerconcert #summervibes #loverera #taylorswiftnation
Life with a little bestie >> 💕✨ #motherhoodi Life with a little bestie >> 💕✨

#motherhoodismagic #newmomlife #girlmom
Celebrating 8 months with our little bundle of joy Celebrating 8 months with our little bundle of joy and I can hardly believe how fast the time is flying ✨🎀

This time two years ago I said goodbye to our first baby at 11 weeks pregnant and I’ll never forget the kindness so many of you showed me. I still have many of your messages saved and thinking of them still brings me to tears 💛

If you are currently in the thick of fertility struggles, waiting, hoping and praying for your time — I see you and hope this gives you something beautiful to look forward to. Thank you for being part of my journey and I’m sending all the love your way 💫
My only goal this summer was to take notice of all My only goal this summer was to take notice of all the little things that spark joy and do them as often as possible 💫

{soft living, wellness, new motherhood, happy habits, mindfulness, cozy hobbies, be present, Pinterest aesthetic, summer vibes, mood board, wellbeing}
We all know making time for hobbies is a healthy h We all know making time for hobbies is a healthy habit that we can do more of. So if you’re wanting to make more time for yourself but not sure which hobby is right for you, this guide is for you!

✨These 36 hobbies split across 6 categories are PERFECT for your 30s but can also be enjoyed at any age and are meant to help you discover new activities or reconnect with childhood favorites✨

PHYSICAL 
get you moving, support your health, release stress and give you a boost of endorphins

INTELLECTUAL
keep your mind sharp, expand your perspective and help you follow your curiosity 

CREATIVE
allow you to express yourself, tap into playfulness, relax and unwind 

OUTDOORSY
immerse you in fresh air, bring you scenic sights and foster your spirit of adventure 

SPIRITUAL
nourishment your inner world, allow you to feel grounded, connected and more present 

COMMUNITY FOCUSED 
provide a sense of belonging, foster connection, deepen relationships and encourage collaboration
 
Be sure to swipe through the list and SAVE for later! Let me know which ones you’ll be trying more of 💕
This is your sign to consolidate all of your arts This is your sign to consolidate all of your arts & crafts into a little cozy hobby cart! ✨💛

My random art supplies have been scattered about in various rooms & closets in my home so I FINALLY got around to organizing them 🎨 

From scrapbooking, to coloring books, painting, and decoupage tools — these cozy crafts are now easily accessible and hopefully will make finding the time for creative hobbies to be a tad bit easier ☺️

Let me know if you’re also in your cozy hobby era! And let me know which hobby you want to make more time for 👇🏼
One of my goals is to make my evening routines scr One of my goals is to make my evening routines screen free and as cozy as possible ✨💫

Last night, that looked like an everything shower, a hydrating face mask in my fluffy new strawberry robe, a hot cup of peppermint tea and watercolors in bed. Literally couldn’t think of a more perfect, relaxing way to unwind 

I finally organized all of my craft items into a little hobby cart that I’ll be sharing with you all tomorrow! And I hope to give you some ideas on how to slow down and make the most of the time you have for yourself because we all deserve a little coziness and self care ✨💫

#romanticizeyourlife #eveningroutine #eveningdiaries #selfcarediaries
My goal is to make my evening routines feel a litt My goal is to make my evening routines feel a little more special this season with lots of self care and cozy hobbies ✨💛 

Last night, that looked like an everything shower, a hydrating face mask in my fluffy new strawberry robe, a hot cup of peppermint tea and watercolors in bed. Literally couldn’t think of a more perfect, relaxing way to unwind 

I finally organized all of my craft items into a little hobby cart that I’ll be sharing with you all tomorrow! And I hope to give you some ideas on how to slow down and make the most of the time you have for yourself because we all deserve a little coziness and self care ✨💫

#romanticizeyourlife #eveningroutine #eveningdiaries #selfcarediaries
I know so many people are already posting about Fa I know so many people are already posting about Fall but am I the only one who is happy we still have a few more weeks of summer? ☀️ 

Since we have some time before we switch to cozy drinks, this #matchamonday is starring one of my absolute favorite combos… an iced mango matcha latte 🥭🍵

The sweet & earthy flavors work sooo well together, not to mention the layers are super pretty! 

Here’s your sign to make one

All you need is: 

✨ 1 tsp ceremonial grade matcha mixed with 1/4 cup hot water 
✨ 1 cup your choice of milk 
✨ 1/2 ripe mango mashed

Whisk the matcha and hot (not boiling) water and set aside. Mash ripe mango and add to glass. Top with ice, milk and matcha! 💛

Let me know if you’ll be making this and if you’re currently hanging onto summer vibes or leaning into early Autumn
For all the women in your 30s — cheers to trying For all the women in your 30s — cheers to trying new and old hobbies, connecting to your inner child, fully embracing all the things you love and feeling so much more confident in who you are 💕💫 

#romanticizeyourlife #lifeinyour30s 
#joyfulliving #smalljoys #cozyhobbies
Happy Monday! Here’s a gentle reminder that your Happy Monday! Here’s a gentle reminder that your morning routine doesn’t have to take long for it to be impactful. Adding little moments of mindfulness can do wonders for your physical and emotional wellbeing and even 5 minutes of self-care can set the tone for the day 🦋💕

Since my mornings are a bit more chaotic now, following my 3 step formula to nourish, move, and practice self care has been SO helpful during this phase of life 💫. And I hope it does the same for you! 

Swipe through for some mindful exercises that take less than 5 minutes and comment WORKSHEET if you’d like to receive my free, printable Mindful Morning worksheet straight to your inbox 

Here’s to making our morning routine feel a little more special, even on those extra busy days ✨

#healthylifestyle #healthyhabits #romanticizeyourlife #happyandhealthylife #joyfulliving #softwellness
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