Your Money Will Be Funny, and Other Hard Truths for Entrepreneurs

Tips for freelancers

August has been an interesting month for me. In just the span of a few weeks, I’ve had my most profitable month yet as a freelancer. While the assignments rolled in this month and I scrambled to deal with them all, I thanked God for continuing to open doors for me and send opportunities my way. While I diligently scribbled in my gratitude journal, there was one thing I tried to put out of my mind:

My money is funnier than Chris Rock at the Apollo.

Despite racking up healthy invoices for the month (and it ain’t over!), none of them have paid out just yet. And while I wait for the checks to start rolling in, Sallie Mae, Ally bank, and Capital One have been blowing up my phone like it’s the party line.

Being your own boss is about more than just networking, finding clients, and doing great work. More often than not it’s also about knowing how to survive through the lean times when clients haven’t paid you yet and every single bill you’ve ever had comes due.

While I’ve been doing pretty well to keep up with the demands of my life so far, this month found me shelling out more money than I expected early on and waiting (and obsessively checking my mailbox) until I can make that much-needed trip to the bank.

While there’s tons of advice out there for entrepreneurs and freelancers, here’s what they don’t tell you: Unless you’re Mitt Romney your FICO score may take a hit, your finances may cause you to lose several nights of sleep, and if you don’t find ways to cope with the stress, you’ll be running back to the job you hate before things can turn themselves around.

As I mentioned in last week’s #GOALdigger newsletter, I’ve decided to just not worry about it. I ignore the calls, don’t spend time worrying about how many points I’ll lose on my credit score, and I am confident that I’ll square up with all of my creditors once the paid invoices start rolling in.

But after learning several lessons the hard way over the course of the past two years, my goal is to save you some time and unnecessary migraines by putting you up on game about what to expect if you aim to make entrepreneurship or freelancing your career.

Shall we?

You will get frustrated

Frustration and being your own boss go together like greens and cornbread. Just expect it. In the beginning you might be frustrated by the slow (or seemingly non-existent) return on your efforts, but fret not. If you stay the course, continue to work hard, and constantly adapt to the needs of your clients (or editors or readers), you’ll be just fine.

You’ll question your decision to go solo

Frustration often breeds doubt, and when you start doubting yourself and your abilities you’ll wonder what the heck prompted you to try to be your own boss in the first place. This is normal. If you aren’t scared then you’re either amazingly lucky, Iron Man or not really giving 100% to pursuing your dreams.

Failure is an option

Listen, I’d be lying to you if I said you’d never fail. Failure is a very real and present side-effect of being your own boss. And while it may happen to you that doesn’t mean you’re doomed to live a life working for someone else. What we see as “failures” are often moments of great learning and opportunity. Learn as much as you can from your missteps and commit to never making the same rookie mistakes twice.

Vacations will be rare

Since going solo I’ve traveled to London, Paris, the Bahamas, Milwaukee, and I’m prepping for another mini-vacay next month. But you know what happened on each of those trips? I’ve worked. Being self-employed means that often times if you don’t work, you don’t get paid. So while I had an amazing time on each vacay, it was tempered by the fact that I had to cut my nights short (or extend them) just to finish up some work.  When you’re first starting out, vacations may not only be rare, but totally impossible. Just know that this, too, shall pass.

It will all be worth it

Despite all of the struggles, the questions, and the doubts I’ve had over the last year, I wouldn’t trade it world the world. Now that I’ve been on my own, creating my own schedule and being able to be flexible to my needs, I can’t imaging going back to the 9-to-5 grind of a “regular” job. Have things been easy? Hell no! But they’ve totally been worth it and have shown me that anything is possible if I put my mind to it and focus on my goals.

Are you self-employed? What other hard truths would you share with wannabe entrepreneurs and freelancers? Please leave a comment to share your experience.


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  • Jessica S

    When I was self-employed as a publicist, I had a hard time with my clients paying on time. A hard truth I had to learn is that people don’t always care that them paying on time may make the difference in you paying a bill or buying a meal that day, week, etc.

    I’ve since gotten a job because I just could not rely on other people for my income…I needed something sure. I no longer practice PR anymore (I give advice/pointers when asked) but that was something that really frustrated me.

    • Britni Danielle

      Yeah, it can be tough. But i’m sticking with it for now & adjusting. It’s definitely opened my eyes and taught me I want to make my income from my own projects. The rest will be icing.

    • AJ

      I would suggest finding work with established agencies. Its great actually. They ask you for your rates and 90% of the time accept it. From my experience, I have never had to haggle with agencies. But with individual people.. Ugh, forget about it

      • Britni Danielle

        Good advice, AJ!

  • African Mami

    1.) Time
    You have none for yourself, all is dedicated to the success of your venture.

    2.) Believers
    There will be a lot of doubters/naysayers. You must firmly believe in yourself and your ability in entrepreneurship, otherwise they might get to you.

    3.)Not confident
    There are times you will find yourself questioning your ability especially, when you look at other very successful ventures. Encourage yourself by knowing that a journey of a thousand miles begins with a single step.

    • Britni Danielle

      Thanks for sharing, sis! You are sooooo right about these, especially the believers!

  • Darren

    great write up, I enjoyed hearing your thoughts on timely payment, me being an indie media maker I find not having a steady paycheck to be a problem. I often find myself throwing more coals to the fire though, I constantly remind myself that I am still young and still need to establish myself in the industry so that I can make these demands for more prompt payment with out it ruining or tarnishing my face.

    When your working alone I feel the hardest part of dealing with money is that your actually putting on a different hat becoming that other role that is usually handled by an accountant or accounts person at a larger company. Being self employed is a process that takes time to be able to wear these different hats and I remind myself daily that I may suck at this aspect of my company now but I will soon master them all.

    thanks for the good thoughts on a ever pending topic.

    • Britni Danielle

      Darren…you are SPOT ON! We often over do it just to make sure we have money coming in, but staying on top of invoicing, payments, and the like is also a full time job.

      Good luck in your efforts! I hope you stop by and read/comment again :)