My blog and business, She Dreams of Alpine, is now over 4 years old, so today I wanted to share a few of my top lessons learned from entrepreneurship.

My whole young adult life the messaging had always been:

Get the good grades
Get a good degree in college
Get a career with that degree
Advance in that career for the next 30+ years
Retire with lots of cash in the 401k

And while that isn't necessarily *bad* advice (I'm grateful for that experience), it also left me in a mental pickle in my late 20's when I wasn't "feeling excited" by the engineering career I was in any longer.

The idea that I had only worked as an engineer for 7 years and still had 23+ years left to go felt SO DAUNTING. But it also felt like one of those decisions that I couldn't go back on. It felt like a sunk cost because engineering is what I had a paid DEGREE in.

But then, on long drives to and from my field office where I worked, I started listening to podcasts and stories from other humans who lived WILDLY different lives than the one I had always been sold... and I began to wonder, "Why not me?"

Why couldn’t MY life and work be just as *WILD*.

So I began to dabble in a new passion. I started my blog, She Dreams of Alpine.

And at first, it just felt like flirting, but quickly things got serious. I began working in the evenings after my full-time job and some weekends on the NEW thing I was creating: my business... She Dreams of Alpine. All my energy and spare time went into this.

I felt I owed it to myself to follow my curiosity to wherever it lead me, like THIS was my next great adventure.

I was Frodo embarking on an important journey.

Not knowing what the next step was, but trusting that the path would reveal itself along the way.

Each step forward into building up my blog and following my curiosity led me deeper and deeper into possibility. What if I COULD turn this side thing, into my MAIN thing? What if I could earn a living doing something I love, and also unlock the location freedom and time flexibility I was craving?

The dream morphed into: Build a thing that would allow me to do work I love, live where I wanted to live, and to have the flexibility to make my time more adaptable to what I wanted to do, when I wanted to do it.

Go for a hike mid-day? Yes please! Work a Saturday instead of a Tuesday because of weather window? YES! Go spend time with my mom when she ins’t feeling well and be able to take my work with me? Yes, and yes. Travel the US in a van with my partner and still earn a living? Yes PLEASE. Take a month off to thru-hike the John Muir trail? YESSSSS! (which I did, by the way, in 2020).

I started my business, on the side, in 2018.

I took that idea full-time in 2019.

4 years later - and I'm still here (even surviving through a pandemic to boot) and I’m happy to report... I don't regret one single thing about the journey I embarked on to become my own boss and pursue/build a life that felt like a full-body “fuck yes” to me.

It hasn't always been "easy" (and thanks to backpacking and the mountains I know that many good/worthwhile things aren’t necessarily “easy”) but... it’s been FUN and WILD and full of unforgettable memories and joy and I've grown 10x more than I would've staying in my engineering career maintaining the status quo doing work that no longer felt meaningful to me.

So today, I wanted to write a post about some of my TOP lessons learned from being an entrepreneur these past 4 years from turning my side business into my full-time dream business (and I’ve also asked my friend, Marie-Pier Tremblay from Self-Growth Nerds) to share a few of her own as well at the end of this post.

Want to start your OWN side business?

Marie-Pier Tremblay and I have recently partnered up to create a brand new live coaching experience for adventurous souls who want to start their own “side-business” so that they can grow it into their #dreamjob – just like Marie and I both did.

It’s a 4-month LIVE coaching experience with Marie and I as your guides, and by the end of our time together, you'll have officially launched a side-business that you’re excited to wake up and work on each day and have a plan to eventually work for yourself full-time (if that’s what you want!)

Join the waitlist now if you want to learn more about this opportunity to work with 2 badass women who've both transitioned from more traditional careers into full-time entrepreneurship so we could do more of what we LOVED and get the time, location and financial freedom we craved.

Now, lets dive into those 15 lessons! The first 10 are from me, and the last 5 are from my friend and Sapling Side-Biz Coach Partner, Marie-Pier Tremblay.

Allison’s (aka She Dreams of Alpine) top lessons learned from starting her own business:

1. Keep it simple.

Of course, when you’re building your own business, you can do whatever you want. It’s YOURS after all. But I’ve personally found a lot of value in focusing in on only 1-2 things when I was getting my business started (instead of trying to do 100 new things all the time).

For example, when I started out, my main focus was building the blog and growing my traffic to the blog.

Then in 2018 I started creating the Backpacking Badass Program (my signature coaching program that teaches women+ and underrepresented genders how to become safe, confident and self-sufficient outdoor backpackers). Then my focus became entirely that program. Creating it, delivering it, marketing it, and growing it.

I focused on just my program and the blog for a LONG time before introducing any new “offers” into what I do. The Sapling Side-Business Starter is my first bigger NEW coaching offer in nearly 4 years of starting my business. This focus when I was getting started allowed me to get really good at those 2 things in my business and helped prevent me from getting “burned out” and overwhelmed from my business. When you’re starting out, you are “all-the-things” (marketer, CEO, sales, creator, coach… all of it) and so you need to keep it as simple as possible in order to get momentum and traction on what really matters.

2. Be flexible and adaptable.

If you’re starting your own business you need to be prepared for the fact that THINGS CHANGE. If you are in resistance to that reality that “things change” you will constantly be upset and angry at things that are often out of your control.

Many people fuss and complain about social media algorithms, for example, but in my opinion its not worth getting upset about. It’s just part of the “game” of business.

When change “triggers” me, I find it more helpful to ask myself “WHY am I so bothered by this change?” And when I put myself into a state of curiosity (instead of being a victim), I’m better able to look for solutions to the challenge and become more naturally adaptable to the situation.

3. Owning your own business is 50-50.

There are good AND bad things about owning your own business. Its not all rainbows and daisies when you work for yourself.

Some of the things I LOVE about having my own business are:

I get to do work that I love. I get to teach people about the thing that changed my life, BACKPACKING, that is a dream come true! And in doing so, I’ve gotten to help hundreds of other women change their lives too through learning backpacking and being confident on the trail.
I get to employ other women and provide jobs (and also give them remote work and time flexibility)
I get to be CREATIVE every day
I get to plan the year around MY schedule and energy
I get to make on-the-fly travel decisions and adventure calls
I get to take 6-8 weeks of vacation (because that’s something I've determined that I wanted for myself)
I get to live where I want to live
I can work from anywhere
I am learning and growing constantly
… so many great things!

Some harder things about owning my own business have been:

I have to be DILIGENT with my mindset work because owning your own business will bring up a lot of your “negative self-talk” and “self-doubts”
I am responsible for my business making money so I can pay my bills, pay myself, and pay my employees (which can sometimes feel like a lot of responsibility)
Sometimes owning your own business is lonely and isolating (especially when your family doesn’t understand what you do for a living)
There is a big learning curve - and I’ve had to learn to “reframe” failure because that is a constant part of owning a business (I now like to call “failure” > “plot twists” instead, thanks to one of my coaches, Simone Seol!)
I am the “face” of my business, and sometimes I just want to be introverted and crawl onto the couch and hide.

But for me… the pros outweigh the hard bits, and feel more in alignment with the life I want, so I love owning my own business and being my own boss. It’s mostly just important to note that Life is 50/50 and so is having your own business… and so is working for someone else. There are always pros and cons, good and bad bits.

4. You won’t always know the “how” for your dream.

Part of owning your own business is understanding that you won’t always know “how” to do everything you want to do - especially if you have BIG goals.

So instead, you show up everyday taking the next step forward. Just like on the trail. We often know the goal (the mountain), but we don’t always see the full path to get there. But we just keep making those small steps forward, and pivoting as needed to adapt along the way toward our goal.

The tiny steps, the mindset work, and consistently showing up …. That’s what makes your success as business owner inevitable.

5. It’s safe to pursue your JOY and curiosity.

People used to tell me that it would be “unwise” to build a business around something I’m passionate about.

You’ll get burnt out
You’ll “fall out of love” with that thing
Work isn’t meant to be “Fun”
Etc. etc.

But, now after 4 years of chasing my joy and curiosity and building a business that is in alignment with both the work I want to do AND the life I want to live… I’ve found that pursuing my joy is one of the greatest gifts I’ve given myself.

I personally believe that life and work don’t have to be an “OR” relationship… it can be an AND relationship.

Work I love AND can earn a living from.

Work I’m passionate about AND allows me to live where I want to live (or travel and be nomadic!).

Work that fills me up creatively AND allows me to do things like taking a month off to go thru-hiking the JMT.

Passion. Flexibility. Creativity. Freedom. Fun. Fulfillment. Joy. Growth.

Having my own business has unlocked these things for me in regards to what I do to “earn a living” – and while I never *hated* my job as an engineer, I can’t say I’d describe it with the same endearment as the job I’ve purposefully and intentionally created for myself now.

I live in the AND now. Not the OR.

Marie and I are going to talk all about this “AND” relationship with our clients inside the Sapling Side Business Starter Coaching Program.

6. Invest in Yourself to Make Faster Momentum on Your Dream.

From the very beginning of my business journey, I *knew* I didn’t want to take years, and years, and YEARS trying to “trial and error” lots of things and figure it out fully on my own (often people do this in an effort to pinch pennies and be frugal, but aren’t thinking through the UPSIDE of investing in themselves).

Early on, I believed that an investment in myself to learn from others who have gone before me could pay DIVIDENDS in my time and making my DREAM a reality faster. And most often, many of the coaching investments I made in myself paid for themselves within only a few months of implementing what I had learned from coaches.

I want to encourage you to seek out mentors that have done what you want to do and are living the LIFESTYLE you want to live - and learn from them if you have the opportunity to do so.

Believe that your worth that kind of investment and then get to work on getting as much value as possible from what you’ve learned and implementing that.

One word of caution though - be careful who you choose as your mentors, because some people may have “success” in one area of their life, but then might not be living the same kind of lifestyle you want to live. Make sure their life values are matching up with the life values YOU want as well.

Also - Your mentors are just that… “Mentors”. When making decisions about YOUR business, always makes sure that it is in alignment with what you REALLY want to be creating. Learn from others, yes, but trust yourself and your intuition always.

7. Learn to enjoy the “walking” as much as the “destination”.

One of my favorite quotes is, “The person who loves walking will walk further than the person who only enjoys the destination.”

I have that taped to my computer.

That quote reminds me that… this work I’m doing, this business I’ve created, and the life I’m living because of it… This IS the Destination… the living!

I still have big goals for my business and life, but “learning and doing and being” the person I am in pursuit of those goals is JUST as enjoyable to me as the “destination” of those goals.

I’ve found that the “destination” and “goals” just keep changing as we grow… so the sooner we find immense pleasure in the “walking” and the work we do on a day-to-day basis… the sooner we REALLY start living and enjoying this beautiful life of ours.

8. You don’t have to do it alone!

Make your best effort to connect with other entrepreneurs as you’re starting your own business. Make new friends, sign up for business events, and meet people online whom you can talk to.

Here are examples of how I’ve done this for myself:

I made lots of entrepreneur friends online (and through Instagram) - by just reaching out in the DMs and saying hello and trying to build meaningful connections (don’t try to just “get advice” from them, be their friend, show that you actually care). This is how Marie and I met back in 2020.
Go to entrepreneurship live events. Some of my best biz friendships have come from events I attended. Shoutout to Christina and Roslyn! Love you two.
Find an entrepreneur meetup group in your local town. I found one where I live now and go to monthly meetings there. I’ve already made quite a few new friendships from those events.
Join coaching programs that are more intimate where you have the opportunity to meet like-minded people who are in the same place as you. That’s one of the reasons we created the Sapling Side Business Starter - so that we could connect a small group of aspiring entrepreneurs together and so y’all could grow together!

Working for yourself can feel lonely and isolating (espeically because most people in your life aren’t going to “get it”), and its really lovely to have friendships you can tap into and get support from throughout your journey. There are many ways to make these connections!

These are 2 of my biz besties, Christina and Roslyn, below. We met at my first entrepreneur event that I attended way back in 2018. They were the cheerleaders to my idea to create the Backpacking Badass Program. They believed in me when no one else did, not even myself.

I was all like, “Man I don’t know… maybe it’s a bad idea,” and they were all like, “THIS IDEA IS AMAZING. GO DO IT. NOW!”

And I did it. Now here I am… 1,200+ students later enrolled inside my Backpacking Badass Coaching Program. Thanks for encouraging me to go for it y’all. :)

9. Be organized from the start!

Do yourself a favor and try to be as organized as possible when you’re getting started, it will save you SO MUCH time as you start to grow a small team.

Some examples:

Have a system to manage your day-to-day tasks and projects. I use Asana with my team now, but I started with Trello.
Use a Password Protection System like “Last Pass” to store all your passwords and to create unique passwords for the things you sign up for. Be diligent in using this. When you have a team, it will make it easier to share things with them (but safely).
When you start to develop “processes” for how you like to do things, write them out! This will save you lots of time when you start to hand things over.
Get separate biz banking accounts from the start so you keep your business expenses separate from your personal ones (yes, even when your biz is just a side biz).

These are all things I’m excited to share more about in the Sapling Side Biz Starter, because organization and systems are my JAM. I love sharing this stuff with others!

10. Protect your Energetic State. Unfollow, unfollow, unfollow!

In the beginning, it can be hard to NOT compare yourself to others. So my advice is to basically UNFOLLOW everyone who is doing something similar to what you want to do… so that you’re less tempted to compare yourself to them. It also helps you stay FOCUSED on what you truly want to be doing.

When I started my outdoor blog, at first I followed tons of outdoor accounts, but then I found myself just feeling bad about everything I was doing… which resulted in me doing less and just feeling like crap all the time. So one day I unfollowed everyone outdoorsy related (seriously), and I was only following coaches in other niches that I wanted to learn from and be inspired by.

I think its one of the #1 reasons I’ve done so much in 3 years… because I put my head down and followed MY intuition instead of chasing what others were doing and trying to “keep up”.

I once had a girl who was following my account ask me for some advice about getting started with her own business and I sent her some tips over the DMs. Later I found out that she had basically turned around and started copying everything I created. From landing pages, to program, to sales pages… she was trying to be an exact replica of me.

It made me very angry at first. But then I realized that it was only going to be a huge disadvantage to her. She wasn’t being authentic to herself and instead was trying to show up UN-authentically as me… and it came across in what she did. She was always 10 steps behind because she was just trying to copy instead of innovate for herself. Don’t be like that. (1) it’s not cool to the creators you’re stealing from, but (2) you’re honestly aren’t doing yourself any favors by stealing.

Its OK to be inspired by others, but trust that you have your OWN genius and uniqueness when it comes to building your own business. You don’t need to “copy” others to be successful, in fact, it will only hold you back.

Marie’s top lessons learned from starting her own business:

1. You’re the only true expert of your own journey.

Looking to more experienced folks for answers was dangerously tempting when I started in business. If you’re a pro self-doubter like I used to be and don’t tread carefully, you run the risk of losing yourself in the process.

Sure, following instructions brought short-term reassurance - but the trade-off was a brutal disconnection from my inner wisdom, which left me feeling bitter and frustrated.

I had to learn to trust myself more than all the success gurus out there, if I was going to benefit from the freedom we so crave in entrepreneurship. Even if that means making more mistakes!

One of the reasons we created the Sapling Side Business Starter was to give you guidance on starting your own side business, yes, BUT to also teach you how to trust yourself and your own authority when creating the business and life you want to have. We might be “experts” but YOU are the ultimate authority.

2. You are enough right now.

Trusting myself became easier when I realized the quirks I was born with were not to be healed but to be honed.

Hiding in what you think are flaws, are actually your gifts to develop for the world to experience. In the words of James Victore, “the things that made you weird as a kid, make you great today.”

Practicing this belief allowed me to stop comparing myself to other entrepreneurs and trust that I could build an impactful business in full alignment with the person I am today.

3. It’s not about you.

Obviously when you show your true self this way, you open yourself up to rejection. That’s one of the first fears sensitive hearts face in entrepreneurship.

Business is about making offers that people can accept or decline. I used to make their lack of interest mean that I was not good enough, until I figured out that being turned down teaches you what doesn’t work and how to make your product or service better.

Instead of worrying whether people were going to like my offer or not, I started asking more creative questions like: How do I make this a no-brainer for this specific group of people I want to serve?

4. Clarity comes from acting, not thinking.

Asking better questions matters, and taking better actions too. Crafting perfect little plans in beautiful notebooks is fun but not the most fruitful use of your time. I have wasted hours developing the best possible ideas on paper only to discover that no one was interested in reality.

If I wanted to find the best way to help others, I clearly needed to get out of my head, stop obsessing over details and forget about getting another certification so I could step into the arena and learn from my mistakes.

The faster you fail, the faster you improve. So get out there.

5. Passion without breaks = burnout.

I will leave you with this: I’ve found that what all entrepreneurs have in common is passion. That’s wonderful, except that there’s one challenge for me here: Everything tends to fade away when I’m enthralled by what I do.

Who needs to pee or eat lunch when you’re working on a life-changing project?! I was a creative soul on a mission and my basic human needs could wait… until I crashed. As boring as that sounds, our biology has to be taken into consideration if we are to build sustainable businesses.

So I am learning to prioritize rest, spend time with friends and read cheesy romantic novels even when my projects seem so much more exciting at the moment.

I know too much excitement leads me into a wall, and I’m here for the long run.

We hope you enjoyed this reflection and took away a few nuggets for yourself to try on.

Want to start your own side business and work on turning it into your full-time dream reality?