Five Lessons I’ve Learned my First Year as an Entrepreneur (Part 1 of 2)

entrepreneurDeciding to quit my day job as a lawyer was a strange decision for me. It was like it dawned on me one day, “Wait, I can actually quit?” It seemed unreal that quitting was an option. I had gotten so used to my  work routine at that point.

Once I realized I could actually quit, I couldn’t get the idea out of my head. Getting called about deposition dates while I was on vacation, constantly going back and forth with opposing counsels about a few thousand dollars, putting on a show in court, managing my own docket….It had gotten stale and stressful after three years and I wanted to do something more meaningful and challenging. At that point, I had been tutoring law students and bar exam students on the side but aimed to make it my full time career.

So in the last year, I developed my website, started a blog, read books about SEO, got a lot more students, made some lovely online courses, gave a bunch of speeches, met a lot of awesome people, made a lot of very costly mistakes and learned a lot!

I always aim to write for people who want to stand out and do something different – whether that is entrepreneurship or something else. So hopefully you can take away something from the lessons I’ve learned.  With that said, enjoy Part One: Five Lessons I’ve Learned my First Year as an Entrepreneur:

1. Starting a business is not always “Diving in head first” – sometimes it’s a wade. And that’s okay.

People sometimes say to me, “Wow, you quit your job to start your own business! AND you’re successful your first year!? How did you do it?”

But in reality, but it wasn’t that courageous. And it’s not my first year. There is this perception that people who start businesses spontaneously decide to leave their jobs one day and hang up a sign the next.  And some people do. But a lot of people – including me – don’t.

I had stumbled into bar exam tutoring in 2011 as soon as I passed the bar exam and had become pretty good at it – getting students each exam 100% through word of mouth.  When I started to tutor, I wasn’t consciously deciding that I was going to work toward building my own tutoring company. Actually, at the time, I thought I’d end up starting my own mediation business. I was just tutoring on the side because I enjoyed it and found it meaningful (and I made some extra money!).

If you are looking to start a business or any kind of new venture, you do not have to drop everything, quit your day job, take out a million dollars in loans, and jump into the deep end (for the vast majority of cases). Sometimes, it’s less of a dive and more of a wade. It’s not one decision. It’s a series of decisions. Dipping your toe in. Getting in the pool. Wading deeper. Putting your name out there. Starting a website.  I am a big fan of starting slow and growing organically. Slow growth lets you know if you are in the right field and if what you think you want to do is all it’s cracked up to be.  It’s less risky. It gives you flexibility to change directions if you need to. And it saves you a lot of stress in the meantime.

2. Get over yourself. Rejection and Failure Are a Necessary Part of the Process.

To be a business owner, to make art, to help people, to spark a connection, to do anything meaningful….it is not enough to create something. You actually have to share it. This means you have to approach people. Send a lot of e-mails that don’t get answered. Make phone calls that don’t get returned. Submit articles that don’t get published. Give speeches that don’t always garner that much enthusiasm.   Write blog posts that no one reads.  You don’t have to hustle anyone, but you do have to put yourself out there. Sometimes with very little response or reaction to what you say.

Business certainly exposes you to this lack of response – this feeling of being ignored. I know I’ve experienced it. Don’t get me wrong; I’ve had several weeks where my business goes great and I’ve felt very successful. But I’ve also had weeks that seemed to drag by and leave me feeling ignored, unimportant, and sometimes even bitter. I remember after having a particularly slow week that dragged on forever, I was asked to give a speech to pre-law students at a local college. I was hoping it would rejuvenate me. Instead, only a few people showed up and half of them were on their cell phones. I went home, drank two glasses of wine and wondered if it was worth it to keep my business going.

Failure and rejection – even though they are necessary to moving forward – aren’t always easy to deal with especially when you are on your own and committing so much time as well as physical, mental, and emotional energy to the very thing you are failing at.

How to cope? I slowly started giving myself (what I called) “courage points” for just doing something that required courage and not paying attention to the result. I’d make myself do one “courageous” thing every day – small or large. I’d give a speech and be happy to gain a “courage point” (…even agreeing to give a speech earned me one!). I’d approach a client and give myself another courage point. This made the outcome less important than the fact that I was actually DOING something and growing. I didn’t keep track of courage points or anything like that, but some weeks I’d make it a goal to do one courageous thing and earn one point every day. This helped me to refocus on what I could control (the effort) and not depend so much on what I couldn’t control (the outcome).

Recently, I heard of this project called “Rejection therapy” –  where the goal is to do something every day where you are guaranteed (or almost guaranteed) to get rejected. The idea is to be aware of how fear controls our lives, not get so attached to outcomes, and permit ourselves to fail. The end goal (from my perspective) is to look at rejection (or failure) as a step in the learning process or even a game rather than a statement about who you are. The guy who invented it did some pretty funny things (all videotaped!) – he asked to borrow $100 from a stranger. He asked for a “burger refill” from a fast food place. He went to Petsmart and asked for a haircut. He asked a dry cleaning company if they would dry clean a tire. Everyone said no. And that was the point. But he learned a tremendous amount in the process.

I was very impressed by the idea. It seems like such a unique idea in this day and age to turn “failing” into succeeding. It puts a different perspective on business and life. It shows we tend to take ourselves too seriously and hearing “no” is not going to devastate us. … It makes it worth it to try.

3. Simplify Your Business Life by Getting Rid of Anything that doesn’t Fit with your Vision. 

Simplifying is underrated. It is very difficult at first but it becomes extremely rewarding if you stick with it!

I recently did a “30-day challenge” with one of my BFF’s. The 30-day challenge consisted of wearing only the same ten items for thirty days (not counting socks/underwear/etc – but including shoes!).  I wasn’t sure what my goal was going into the challenge, but I hoped it would teach me something about myself and my relationship with my material possessions. So I wore a black t-shirt dress, a red dress, high heels, tennis shoes, leggings, a yellow t-shirt, a long-sleeved jogging shirt, a pair of pajama bottoms, a coat, and a black sweater– for 30 days. In the beginning, it was really hard and annoying and truthfully, I would have given up if I didn’t have a friend doing it with me.  I missed wearing my other fall clothes. I was always too hot or too cold or too annoyed by the prospect of having to handwash my dress in the sink after spilling something on it (again).

By day 20, I loved it. I never thought about what I was going to wear (and saved a lot of time that I’d normally spend picking out an outfit).  I only had a couple of clothing options (and usually it came down to “the clean one” so I REALLY didn’t have to think about it). I found myself start to take care of what I was wearing. I started calling the two outfits that I actually wore out my “uniform” (the other outfit was for exercising in and the other for sleeping). I did this challenge primarily to convince myself to detox my apartment and closet of all of the nonessentials. But, I realized that limiting choices and simplifying work life can be just as important.

So it led me to simplify my work too. I sat down and really thought about what my vision for the future of my business was. I decided what kind clients I want and what kind of clients I need to say no to. I limited the kind of work I do. I started to say no to people and opportunities that really do not fit into my vision.  I’ve started to work on one or two projects at a time rather than working on ten projects.

It was hard at first. But just like with my clothing project, I have begun to really relish the fruits of the effort. I find myself carefully spending my time on the people and projects that matter most and I find I am able to happily delegate or simply turn down the rest.  This results in better products and a more focused business. Ask yourself the question “What is my vision?” and “What am I doing now that doesn’t directly advance my vision?” Then whatever it is, stop doing it. It is painful at first but worth it in the end.

Even if you do not own your own business, asking yourself the question, “What can I simplify in my life?” is extremely freeing if you take some time to really think about and implement the answer.

4. Being an Entrepreneur is Limiting as much as it is Freeing

Many people think, “Wow it must be great to work for yourself. You get to make your own hours. You work when you want. You work from home in your pajamas….”

And it is great.
I work when I want, how I want, where I want.
I take time off when I want and travel a lot.
I do work in my pajamas sometimes.
More than that though, I LOVE the process of creation, sharing, art (yes, bar exam outlines are art J), meeting fabulous people, rearranging everything the way I want to.
I am 100% in control and I like to think that I don’t answer to anyone.

But there are a lot of things that are limiting too –and I think the limitations just depend who you are, how big your company is and a variety of other circumstances. Mine are as follows:

  • Being the owner of the company, bar exam tutor, speaker, website designer, blogger, secretary, and accountant all at once is exhausting and it requires a lot more time than if I was just one of those roles.
  • I don’t make money when I don’t work. Now hopefully that will change in the future (I’m all about “passive income”) but for now if I go on a two week trip to Hawaii that is two weeks without an income. I don’t have a salary. I don’t have vacation pay or personal days or paid leave.
  • It is true that I don’t answer to anyone but sometimes I feel as though I answer to everyone. It’s MUCH harder to turn down a client when I need to make an income. I do when I need to but it is not the instantaneous thing it was before when I had a paycheck to back me up.

I’d never trade entrepreneurship for anything in the world. But just because you are on your own does not mean you are free to do whatever the hell you want. It comes with its own set of limits which are worth considering prior to starting a business.

5. Constructing Boundaries between Work and Life is Hard but Necessary.

As an entrepreneur, when you come home from work, it is very hard to “turn it off”.  Mostly because you don’t come home. You are already at home, working from home. Home becomes work.   It seems like you never stop. Your work is sitting on your living room table, your desk in your room, your nightstand, taped to your wall. It’s in your personal e-mail inbox, your personal voicemail box, your personal space. Work is so mingled in with life that it is very hard to NOT think about work 24/7 since all of the traditional boundaries between work and the rest of your life have become blurred or erased.

I listened to two fabulous fizzle podcasts on work-life balance which inspired me to do the following things to help myself turn work off. If you find work-life balance tricky (which you will if you are an entrepreneur, or someone who frequently works from home, or someone who is slightly neurotic like myself…), it is worth it to listen to the podcasts or, at the very least, read some tips below:

  • Remind yourself why you are doing what you are doing. I am not an entrepreneur so I can work 100 hours a week – the point is to be able to create my own schedule (which includes some time off!) This alone helps to remember the bigger picture and take breaks and not feel guilty about that afternoon glass of wine…
  • Go on a walk around the block after work is over. Walking around the block after my work day is over is kind of like driving or walking home from work. It creates space between work and the rest of life so that it is easier to transition into relaxation.
  • Schedule set times off then follow through with them. Making it a point to make plans with friends or family at night and saying “At 7:00 PM I am done” – then actually being done- is crucial. I’ve found that doing this makes me more productive during the day because I know I will take some time off at night.
  • Schedule one day (or half day or whatever) off per week – It’s easier than you think and very good for you. Taking every Sunday off (a tradition I have kept for a long time now) is a real and necessary break from work.
  • Make it a point – and a goal, even – to travel. This not only lets you get a mental break from work, but paradoxically you might have your best ideas when you are vacationing! When you change your location, change your routine, and change the scenery of your life and mind, you actually create enough space between work and life that it is almost as though you subconsciously begin to view your work from a birds-eye view (even if – especially if – you are trying not to work or think about work at all!). I have found myself on vacation, swimming in the ocean, and BAM, I think of a project that I should start. Or I slowly realize the obvious solution to a big decision I have been trying to make. I even decided to quit my job (and realized it was possible) walking down a beach in Florida. None of the biggest, brightest, most important decisions I have made happened while I was working, or thinking about work, or even at my desk. They have all happened while I was away. And it made me a firm believer that long term breaks are ironically, one of the most productive ways to spend your time.

Thanks so much for reading this post. I hope you’ve enjoyed “Five Lessons I’ve Learned my First Year as an Entrepreneur – Part One”. Part Two is coming up.

I’d love to hear your thoughts in the comment section below.

Ms. Ashley Heidemann graduated as the number 1 law student out of over 200 students in her class of 2011 at Wayne State University. She now works as a tutor for law students and the bar exam. She also offers a Law School Preparatory Course for students interested in learning the skills necessary to achieve a high GPA in law school.  

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