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What no one told me about starting a business

By |Last Updated: September 5, 2014|8 min read|


Editors note: This personal account was actually first written a year ago, but many of the learnings still hold true. I hope the tips here help you if you’re thinking about starting your own business or have just gotten started.


There are so many things you should have in place before starting a business of your own. Practical and logistical considerations most often get all the attention, but there’s also many psychological and social facets surrounding your career shift. Nothing can prepare you for the spectrum of emotions experiences of running a business other than just doing it; in a sense, all you can do is prepare to be unprepared. With that unsettling notion in mind, hopefully my experiences will give you some insight on how to be a little more prepared than I was at first.

Your friends probably won’t understand

Many of your friends will not understand why you no longer “hang out” with them, or why you don’t come around as often. When you’re collecting a steady paycheck it’s easy to be lulled into a false sense of security that a check will be coming your way every two weeks, so you probably don’t feel the urgent need to hustle every damn day to earn your keep. That’s not to say that a steady 9 to 5 does not require “hustle”—any job worth doing deserves 110%—but working on your dream requires 210%. If your crowd isn’t part of the startup culture, you’re likely going to get quizzical looks and confused puppy dog head turns whenever you mention frequent all-nighters, working until 11 p.m. on a Friday or Saturday night in lieu of a round of drinks with your buddies.

Find people in a similar situation as yourself

Make new friends. That’s not to say that you have to completely write off your current friends, but your own needs will likely change. I still look forward to seeing the friends who I can just “shoot the shit” with but I also need a group a people I can “talk shop” with. People I can bounce business ideas off of without getting glazed-over looks after only five minutes. These supportive folks might be people in your industry or simply other startup owners. It’s healthy to exchange business ideas, and the support you get from a new group of business-minded people is not only encouraging for your state of mind, it also feeds your soul. We are, by nature, social creatures. Be sure to get out now and again with your best buds, but make time to co-work with like-minded individuals who are as brave (or as “stupid”) as you are. I’ve found great support through two great groups: Ms.Tech and CRAVEchicago. Both are organizations for women business owners. We have a vast range of business types, but at some level we’re all looking for a way to both network and find women who are similarly passionate about what they’re building. Sometimes we collaborate; sometimes we just talk about what’s going on in our worlds that day.

You haven’t saved enough before taking the leap

Everyone under the sun tells you that you should not quit your day job until you have saved enough money to live on for three–six months because ramping up a business takes time and we can’t pay the bills with smiles and our good looks. While this is true, three–six months goes by incredibly fast, even when you have a phenomenal idea and solid executional/growth plan.

If you can stand it and haven’t been “let go,” stay where you are long enough to pay off your debt before leaving your 9 to 5. The mental anxiety of paying off debt while running a profitable business will wear on you faster than a 500 lb. gorilla running in ballet flats.

You will learn very quickly who your closest supporters are

If you think you have a strong support base, you will quickly learn how true this belief really is. Make sure you have at least one person outside of your business with whom you can confide, commiserate, and talk to openly and without judgment on just about anything. I feel I am fortunate, in that I have a strong partner who recognizes and endures my stress-induced mini-tantrums, shores me up when my insecurities get the best of me, and will simply listen when all I need is an ear. For you this could be a former boss or mentor, a life-long friend, or perhaps a parent. For me, it’s my boyfriend, who should honestly be a candidate for sainthood. My hope for you is that you have many people like this in your inner-circle who will love you and guide you unconditionally through all of the rough patches you will surely encounter.

Your level of self-confidence will either skyrocket or plummet. Sometimes both.

Make sure you are prepared for either circumstance. In my case, I cannot tell you how much starting my own company has boosted my self-confidence.

At the same time, you are riddled with self-doubt. Am I making the right decision? What are my employees going to think about X? How is the client going to react when we tell them X? Why did I ever think I could actually pull this off? Who am I to do/say X?

When you start to feel this stream of self-doubt creep in, just remember why you started in the first place. This is your DREAM… your passion… it’s worth fighting for. Maybe you have to pivot. It’s not the dirty word some people make it out to be.

Your network is your lifeblood

It’s been said that by the time you need a network, it’s too late to start building one. This is completely true. Relationships take an extreme amount of genuine effort. You really cannot fake it and there aren’t shortcuts. While you aren’t going to like everyone and everyone isn’t going to like you, do not burn bridges. I live in the second largest city in the States, and it’s been amazing how many times people I didn’t think I was that close with came through for me when I needed help and vice versa. So don’t burn bridges. There is always a way to take the high road even in the most heated disputes, so I encourage you to seek that path as often as you can.

Know your limitations

You can’t do everything. No one can. Know your strengths and learn to delegate. The latter is something I still struggle with. What helps is creating a process that you can teach to someone, guide them, and in time they can take over. It’s twice as much work up front, but pays ten-fold in the long run.

Make time for you and establish healthy habits from the start

You may believe you’re destined to be the next Steve Jobs, but be sure you give your body the attention it needs everyday. Many of us sit at a computer in exchange for money. Just make sure you don’t do that for 8+ hours straight. Design a schedule that allows you ample time to make a healthy breakfast, do a light workout (or an intense one if it suits you better) and make sure you get up and move about regularly throughout the day. I can tell you that in the first year of starting my business I gained at least 20 lb. just because I no longer had a commute to work, no longer walked to get lunch from Whole Foods several times a week, no longer ran after work, etc. Instead I worked from home, ordered out because I didn’t think I had time to cook, and just sat at my computer for stretches far too long. It amazes me that I still don’t need glasses with all of that screen time. Make sure you’re eating whole foods as often as possible, moving throughout the day as much as you can, and consciously setting a schedule that provides you with a healthy work/life balance, whatever that balance may mean for you.

The freedom is unparalleled

Just knowing that you can sleep an extra hour, go for a run in the middle of the day, or take a half-day off when you have no meetings is priceless beyond belief. I have yet to fulfill my dream of being at the beach by 2 p.m. for sand volleyball on the weekdays in the Chicago summers but by golly, just knowing that if I really wanted to, I could make that happen, is a feeling of freedom I wouldn’t change for the world. Above all that, I know at some point that all of my sleepless, anxiety-ridden nights, my dogged preparation and my tenacity will pay off in the long run, but hopefully sooner.

Have you started your own business?

Share your experiences with us in the comments below.

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