12 Things I’ve Learned About Life as an Entrepreneur

nyc street style office attire

On October 2, 2018, I took a huge leap of faith and left my dream job to start the journey of building my own brand. I said goodbye to the cushiness of corporate life (and the benefits, salary, vacation days, colleagues etc. that came with it) not knowing what, exactly, I was getting myself into. 

The decision was scary as all hell, but it was something that I knew I would forever regret not doing.

In the time since, I’ve learned that when people say “with great risk comes great reward”—they aren’t completely full of shit.

Still, the journey hasn’t been easy. Like many entrepreneurs, I’ve been plagued by self-doubt, imposter syndrome, second-guessing, indecisiveness—but I’ve also realized that I’m capable of way more than I could have ever imagined.

So it seemed only fitting that on my one year anniversary of working full-time in my pajamas, I would commemorate this milestone by reflecting on the things I’ve learned thus far.

1. Despite how much you plan, you will not have everything figured out right away. And that’s OK. Making mistakes is part of the process. Learn to roll with it.

2. Use your network. Don’t be afraid to ask for advice. You’ll feel annoying, but you’ll also pay it forward to the next person who finds themselves in your shoes.

3. Work/life balance is a myth. When your livelihood depends on your business, everything tends to bleed into one—but if you love what you do, and if you’re excited about what you’re building, it hopefully won’t feel like work. 

4. Weekends are also a myth. At least most of the time. For me, weekends have become an opportunity to get all the things crossed off of my list that I didn’t have time to do during the week. They are frequently when I’m most productive because I’m free from the distraction of constant emails, phone calls, and meetings.

5. When you actually stick to it, time-blocking your schedule can be a SUPER effective productivity hack. The concept is pretty simple: rather than trying to do 20 things at once, focus on one thing—and only one thing—for a specified period of time without interruption.

Occasionally I’ll use this TimeCube to help. (For ex: I’ll set it for 60 minutes, and then commit to clearing my inbox as much as possible during the 60 minute period. Once the timer goes off, I’ll switch to another task—like photo editing—for the next 60 minute block. And so on…)

6. You will probably spend a lot of time in your pajamas. Some mornings you might even forget to brush your teeth. It’s fine. 

7. It feels good to take advantage of your freedom in small ways. If you had a productive or successful weekend, lay in bed and do nothing on Monday. You’re allowed! In fact…you’re allowed to do whatever you want, because you’re the boss.

8. Be a sponge. If you don’t know how to do something, look it up on YouTube. Take an online course. FIGURE. IT. OUT. When I started blogging I had no clue how to build a website…so I figured it out.

I had no clue how to make a newsletter either—and guess what? I figured that out too. Same with shooting and editing YouTube videos, filming tutorials, and even taking proper photos. (Maria Forleo wrote a NYTimes best-selling business book called ‘Everything is Figure Outable‘ — a genius title, if you ask me.) 

9. Find Facebook groups for your niche and join a few of them. You’d be surprised how supportive and helpful other people in your industry can be. I’ve learned SO much from the blogging & SEO groups that I’m in—more than I would have ever been able to find out on my own. (I recommend Tracie Fobes’ SEO content and her Blogger Education Network FB group, as well as Carly Campbell’s Pinteresting Strategies Course and her Blogging Like We Mean It FB group.)

10. If you have a significant other, they will see you at your absolute worst and your absolute best. They’ll witness you triumph at one moment, and then feel like your soul has been crushed the next. Lean on them for support as much as possible.

If you don’t have a partner, rely on the support of family and friends. It helps to vent to people. Talk things out. Often, a simple phone call or a drink with a friend completely changed my perspective (or snapped me out of a cranky mood.)

11. Learn to outsource the things you hate or that you’re not good at. I used to spend hours and hours trying to edit my own videos until I realized something: it was eating up a LOT of my time, and the ROI wasn’t making it worthwhile. So I hired someone to edit them for me.

Now, I can dedicate the 8+ hours I was spending on videos to things that I’m actually good at/enjoy. The same goes for negotiating contracts and business development. I LOATHED having to sell myself and to go back and forth with potential clients about money. So I hired an agent. Doing so was the best business decision I’ve made thus far. Now I can focus on the creative parts of my business that excite me the most.

12. Keep at it. Ups and downs are part of this whole journey. You know when you’re on a roller coaster and there are moments you think you might puke? But then when the ride ends, you’re overcome with a sense of euphoria because you successfully survived? That’s what being an entrepreneur is like. Chase the euphoric feeling of success—but know that projectile vomiting along the way is, like, totally normal.

Trust the process. It’ll be worth it in the end. Take it from me. I’m writing this in sweatpants while sitting on the couch at 12pm on a Wednesday. And I get to call it work 🙂

I’d love to hear from you in the comments below—have you ever thought about starting your business? Or if you have, do you relate to the things I mentioned above? Share your own lessons about life as an entrepreneur below <3 


  • Meredith
    October 2, 2019 at 5:28 pm

    Congrats on everything! I work from home and relate to a lot of this—PJs and teeth hygiene, especially. And I have a blog on the side, so I’m curious which FB groups you’re part of for blogging, SEO, etc? Thanks, and congrats again!

    • Lindsay Silberman
      October 3, 2019 at 9:15 pm

      you’re right I should have mentioned them in the post! Adding links now 🙂

  • Emily
    October 2, 2019 at 5:32 pm

    Loved this post. Congratulations to you on building a great blog/IG and community on FB. You are a trusted source!

  • Victoria
    October 2, 2019 at 9:38 pm

    Hi! I just recently started following you in on Instagram and I think this blog post specifically SO helpful! I started a, one might say, nontraditional food blog in May and in the couple of months I’ve been teaching myself all the ins and outs of building a website, creating email newsletters, promoting and marketing my brand and so forth! I couldn’t agree more with the risk-taking jitters as I call them. Will people think my content is good? How can I promote it? Can I afford to do this? The results (even though not an over night sensation) have shocked me. I’m definitely going to look into someone to help me part time when I can reach out! Thanks for getting me so inspired to take more leaps of faith!

    • Lindsay Silberman
      October 3, 2019 at 9:15 pm

      Sounds like you’re doing AMAZING. Isn’t it incredible how much women can accomplish if we put our minds to it?!

  • Laura
    October 3, 2019 at 9:04 am

    Yesssss to all of this! Thank you! You are amazing and I appreciate your authenticity and real ness. The road isn’t easy but totally worth it!

  • Bree
    October 3, 2019 at 2:22 pm

    Congrats girl!! I’m definitely grinding it out and blogging in ANY down time I have while working full time. It’s so true though, everything can be figured out!!! And I’ve learned so much about myself through the process.

  • Taylor Cordeiro
    October 4, 2019 at 3:42 pm

    This is great! Going to bookmark this to return to when I need inspiration!

  • Kristi
    December 3, 2019 at 3:27 am

    Yessss! I’ve learned these lessons myself as an entrepreneur. I think the only thing I’d add is that you don’t eat proper meals–taking a “lunch break” is a thing of the past and grocery shopping is best left to your SO or roommate because when you get involved in work, it’s very hard to muster up the will to cook 😉


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