Lessons In Entrepreneurship: 7 Points To Consider Before Launching


At some point in your career you may be there, a forked path in front of you. You’ll ponder your options. You’ll reflect on your career up until that point. Past decisions, advice from mentors, missteps, wins. You’ll gaze ahead, unsure of where to turn.

Choose left, and find a comfortable path. This path leads you down a familiar road. It’s known, it’s safe, and it’s a path with little risk.

Choose right, and find uncertainty. This path is full of unknowns. There is no guarantee and no assurance about what lies ahead. It’s scary. It’s murky. It could be a huge mistake.

This is the crossroads of an entrepreneur. At some point, the draw to make that right turn grabs you and you can’t shake it free.

I found myself facing this choice towards the end of 2013, after staring at this fork for a year. I pondered, I sought advice, and I analyzed and modeled. I wrote a business plan full of buzzwords in a five-hour caffeine fueled cross-country flight “Jerry Maguire moment” that’s never been shared. It was terrible.

Choose right was where I eventually landed. In the end, it wasn’t that difficult of a choice. I was ready for a change. I spent a year contemplating this move. I was fortunate to have two great clients lined up. I had a supportive wife who encouraged me and supported this transition. The risk was there, but I believed deeply I could build something.

I’m now six months in and have no regrets, but its not all frequent flyer miles and travel meals. There are times working for yourself is hard. Really hard. There’s also a tremendous sense of satisfaction when you deliver great results to your clients, sign that deal, and realize you might be on your way to building something special.

Here are a few things I’ve learned along the way.

Be ready to hustle.

There’s a romantic notion around self-employment that your hours are yours, and you have complete flexibility when you work. It’s a myth.

When I pondered my path to entrepreneurship I often wondered if I had it in me. I’ve held a job since I was 14 years old. I used to knock on doors throughout my neighborhood when I was ten, offering to do odd jobs for money. In middle school I rode my bike twelve miles to a convenient store to buy candy, which I re-sold at school to fund my G.I. Joe habit.

That experience taught me lessons that carried over to my current endeavor. Most importantly work ethic (my dad gets a lot of credit there) and a drive to do great work that leads to loyalty and repeat business. In short, when you’re bootstrapping your own company, you better be prepared to work your ass off.

Be prepared to work even harder at home.

If you have a spouse or family, you may struggle to find your balance. Because you have the work hustle above, you’re going to want to pour all your energy into building this new business of yours. Be careful. While the business requires your attention, your family does too. You need a supportive family to make it as an entrepreneur, but more importantly, you have to learn where to set boundaries so that you’re present for them.

If you’re married, keep in mind your spouse is making a huge sacrifice for you to pursue this dream. Your new job might require you to travel more. That puts a huge burden on your family. Don’t underestimate that. You may be pursuing this path to provide more long-term financial security for your family, but be sure you don’t lose sight of short-term needs. I have to admit I really struggled with this in the first few months.

Find mentors and listen to them.

My friend Laurie Ruettimann regularly offered me great advice as I stared at that fork in the road. Yes, working for yourself is liberating. Things that aren’t liberating? Chasing clients for payments, spending a day Googling why your email client isn’t working, bookkeeping, etc.

Mentors keep you grounded, and help you realize the good and bad. Particularly, not to get so caught up in the romantic notion of being an entrepreneur that you're blinded to the less exciting aspects of building a business.

Be flexible.

No matter how well thought out your business model is, be prepared for it to evolve in the first year. Even the best laid business plans might need to pivot as opportunities present themselves.

Entrepreneurship is about creating opportunity at the intersection of demand & skill (among other things). These are both fluid lines intersecting at random times. Be nimble, and be ready to change your focus and shift your plans to seize those opportunities.

I realize this lesson isn’t universal. There are much more accomplished entrepreneurs who champion laser-like focus. However, this is what I’ve experienced firsthand in my journey.

Help others, but be mindful of your time.

This one is a bit tricky. When you’re building a business, time is precious. Most entrepreneurs pursue that path because they have identified professional skills where they excel. Clients pay a premium for this expertise. Any time you spend away from focusing on your clients has a real opportunity cost, and ultimately monetary impact.

This has been a bit of a struggle for me. While I want to share insights and help others in my field, I have to ‘vet the ask’ a bit to make sure the time commitment is manageable.

Want a 15 minutes Skype chat, or input on a quick email? Done. Meeting for coffee an hour away from my house? That’s a three-hour investment that really impacts my day. Entrepreneurs need to manage their time closely.

Find time for wellness.

When you’re not traveling and meeting clients, you’re typically in a home office for hours at a time. That’s a rather sedentary life. I find I have to remind myself to get up and get active. I think it’s helpful to have a rhythm or routine around your activity. Whether it’s exercise, practicing mindfulness, or just getting out for a walk. It's important to schedule and make time for yourself.

I recently bought a standing desk. We'll see how that works out.

You don’t have to start a business to be an entrepreneur.

This is something I explored for years before actually leaving a full-time job to launch . I’m a huge supporter of intrapreneurship. While only a small handful of companies have established programs, you can usually find entrepreneurial outlets even within traditional corporate organizations.

Find a project within your company. Join a non-profit board or volunteer. There are ways to begin gaining exposure to the different aspects of building a business without leaving the stability of your full-time paycheck. The more of this experience you gain, the more you’ll be prepared to choose which path if and when you reach that fork in the road.

These are some of my personal learnings six months into building a new business. Have you followed an entrepreneurial path? If so, please share your learnings in the comments below.