How to overcome fear of starting my own business
March 2, 2010 8:02 PM   Subscribe

How did you feel about starting your own business? Specifically looking for stories from people who left a fairly good corporate job, and how you found the courage to do it to help inform my own decision to stay or leave. (lots more inside)

My personality: Being an entrepreneur has been my long term goal for years. I have always wanted to start a business, and was the very stereotypical kid who was always doing various entrepreneurial things, and even started several businesses and intiatives in college though decided to work "in the real world" post college.

I took this test last week and answered "yes" to 19 of the 20 questions. I consistiently have the nagging thought that I really need to quit my job and start my own company, etc.

I don't know exactly what my company would do, however, and if I wasn't currently miserable at work I think I would stay 1-2 years to figure that out and save more money.

Current job:
I'm an executive at a brand name entertainment conglomerate and my job pays well. I enjoy most of the actual tasks in my work, and the people. It has a lot of perks that make nearly everyone I know jealous. However, I have become extremely bored with the job because I learn incredibly quickly, like to be constantly learning, and my boss is an extreme micromanager who won't let me stretch at all (you can imagine how someone very entrepreneurial would feel about that).

I have over ten years of work experience across the entertainment industry and a top 5 MBA, I'm well respected at work and do a good job. There is definitely potential for me to advance in my current division or elsewhere in the company.

My specific worries/constant thoughts/fears are:

- will it be more difficult to leave as I accumulate more money and power in my corporate job?
- will I make as much money in my own business?
- will I ever be able to buy a house/pay off student loans, etc if I leave cushy job? (I have a side job that will bring in enough money for my living expenses, but saving/progressing financially will be difficult if the business isn't successful)
- will I be lonely/bored/feel like a loser?
- is it crazy to just quit without a solid plan?

If you did something similar - how did you overcome your fear? Did you quit and figure out what you were going to do? or have a solid business plan in place before taking the leap? Most importantly, are you happy you did it?
posted by rainydayfilms to Work & Money (13 answers total) 17 users marked this as a favorite
Many of these answers are dependent on your business. Being entrepreneurial is not enough to guarantee success or failure; you have to know the ins and outs of the industry you're thinking of moving in to, and what the typical margin is like. Real estate investment is very different from owning a store, etc. etc.

Will it be more difficult to leave as I accumulate more money and power in my corporate job?
Do not create a false dichotomy where working for the man exists on one hand and freedom on the other. You can do both, depending on the jobs. Why not start a business part-time, as founder hiring more people if you need it. If you make money, quit, become full time director, if not, you still have your job. More importantly you will have a steady source of cash flow at a time when a business typically needs it and is often posting a loss (start up time). Don't be fooled into thinking "this business would make money/I could make business work if only I quit, did X, bought Y, etc..." Fantasies are fun, but business decisions need clear-eyed assessment.

will I make as much money in my own business?
For someone at your level of salary, almost certainly not. And definitely not for several years. The only exceptions to this would be in highly speculative, highly risky businesses, usually involving finance or real estate of some description.

will I ever be able to buy a house/pay off student loans, etc if I leave cushy job? (I have a side job that will bring in enough money for my living expenses, but saving/progressing financially will be difficult if the business isn't successful)
Well, it really depends on what your mortgage, school fees etc are like. And how you are accustomed to living. It's certainly possible. It's possible to live very well. Anything is possible. It will be incredibly hard in the first few years, and you will fight temptation to pour every spare dime either straight back into the business depriving you of holidays etc, or straight out of the business into your holiday, when the business really needs it. Do you have a partner? This is a big conversation for you and your partner.

will I be lonely/bored/feel like a loser?
Do you feel that way now? If so, then yes, probably. If not, then probably not. A business is unlikely to change your fundamental temperament. You will be bored, lonely, scared, frustrated at times, and happy, joyous, energised etc at others.

Remember, you can always get another 'real' job if your business fails, it's not an irreversible decision.

is it crazy to just quit without a solid plan?
YES. Totally fucking insane, in this economy, I would argue. Being "entrepreneurial" (whatever that means), and building a lemonade stand in college or whatever is _not_ qualification for opening a successful business. Go to community college, do some business courses, develop a business _plan_, make it good enough to get backers (even if you don't want backers), do a feasibility study and a marketplace snapshot. You need to know what to focus on, when, and how. Basic accountancy will go an incredibly long way, too.

Reading between the lines of your post, I can't help but feel you have a pretty idealised notion of what running a business is like, and you're attracted more to the cosigns you have invented for it, and the type of person you think does it, than what it actually is, and who you actually are. Different businesses are different, and run in different ways by different people. What does entrepreneur in this context even mean? It's so vague and ill-defined; job titles you should focus on instead include: accountant, auditor, supply chain and logistics specialist, people manager, marketer, HR, insurer and risk assessor. These are the responsibilities you will have running your own business. Not seat-of-the-pants free spirit wunderkind.

Have you worked for a small business? Do you know - closely - someone who owns one? Have you seen what the day-to-day lived experience is like for these people? Are you prepared to lose a lot of money, for years if not permanently? Are you prepared to give up your holiday and pull longer hours? These things are pretty common for people starting up businesses.

I'm not saying any of this to put you off - you could be really well suited for the job, and power to you, homie. But If you wanna do this, you need to be specific, pick an industry, nail down a business plan, outline how you will make more money than your competitors, and where yours costs will lie. How much money you need to break even, how much to make a profit, etc etc.

I think you should do all this before you quit your job. It can be done before you quit your job.
posted by smoke at 8:49 PM on March 2, 2010 [9 favorites]

I have gone both ways. From a very entrepreneurial situation to a corporate and back. I can tell you that my motivation for leaving the corporate was not money at all. It was all about not working for the man, about making my own decisions and about getting rewarded directly for my own work. You eat what you catch. The decision was not making more money, it is about making money on my own. TO me, being an entrepreneur is not about only coming up with ideas and making them happen, it is about risk and living with it or not. So, will it become more difficult to leave as you accumulate more money and power? Probably, but I posit that the reason is that you will be taking on more outside obligations such as a wife, kids, house, lifestyle etc. Hard to leave when you have a lot riding on your decision and you are already making your nut so to speak. Who knows if you will make enough money in your own business?

Make the move for a lifestyle and happiness not for the money.
posted by JohnnyGunn at 8:54 PM on March 2, 2010

If you want to see something sad, you could watch some actual restaurant entrepreneurs in action in the "Cafe 36" episode of Kitchen Nightmares. They seem competent and well-considered...but, well, you can imagine from the title.
posted by amtho at 9:30 PM on March 2, 2010

Pay off your student loans and save up enough money to last as long as you think you need to see the business through to success or failure. Do not cut into your retirement to do so, but understand that your retirement funds won't grow initially while you're building your business. Don't quit your job and your happy, steady income until you know what it is you want to do and you've built yourself a healthy cushion.

Also, health insurance - make sure you've budgeted that in, COBRA's darned expensive and only lasts 18 months (if you're male & single, you're probably okay on this and can get a cheap individual plan...different story for fertile-aged women or families).

Don't endeavor to start your business just to eschew 'the man' (or because of that silly survey - who *wouldn't* get 15-20/20 on it??) because you'll understand where they're coming from all too soon...lots of administrivia involved in self-employment.

But once you get your ducks aligned, go for it! I'm four months past the point I left my cushy job and I still wake up in a cold sweat some nights; and sometimes, despite the fact that my partner and I are in it together, I feel pretty untethered without the 9-5 - but I'm learning so much, so fast, in so many different directions. It's fantastic - but you have to reconcile yourself with the fact that it's not all lollipops and rainbows and sticking it to the man.

Be realistic, be ready, and you'll be fine.
posted by jenh at 9:43 PM on March 2, 2010

2 years ago I left a mid-level good 6 figure corporate job after 14 years. It was one of the best things I ever did. I was incredibly bored by my old job, I was doing just enough to get by, my heart just wasn't in it anymore. The run up to the stock market peak in Oct. 2007 allowed me to exercise all my accumulated options & most of my stock purchase plan shares (aka golden hand-cuffs), so in early 2008 I had low 7 figures in my bank account and nothing to keep me there. Then an incredible opportunity came my way to go manage a struggling start-up with no safety net and I jumped at it. That start-up closed 4 months later (remember summer 2008 things were starting to get weird and raising money was getting very difficult). Now I'm CEO of my own start-up with seed funding, no safety net, savings greatly depleted, earning a bit less than I did before, but loving every minute, even though we could be shut down in a couple of weeks.

So here's my take on your questions:

- will it be more difficult to leave as I accumulate more money and power in my corporate job?

No, firstly more money means you'll have a financial cushion while you start something. The kids still have to get fed and the mortgage has to get paid. Make sure you can meet your basic obligations for at least a year.

Second, when you start a career you crave success just to prove that you can do it. After you've achieved that you realize its no big thing, so I think its easier to go back to the start line as starving entrepreneur with a desk in the corner of the work shop after you've sat in the top floor corner office for a while.

- will I make as much money in my own business?

Yes & no. You won't pay yourself as much because typically you'll never have as much money as you need to grow your business as fast as you want. Still, unless you reach the very pinnacle of big corporate levels you will never become fabulously wealthy. Whereas life changing money can absolutely happen if your own business is a success. So you trade-in security and good income for no security and mediocre income for unlimited upside potential.

- will I ever be able to buy a house/pay off student loans, etc if I leave cushy job? (I have a side job that will bring in enough money for my living expenses, but saving/progressing financially will be difficult if the business isn't successful)

Many businesses are not successful, failure is part of the journey. Being your own boss means not having a safety net. So yes, if you're a successful entrepreneur then of course you'll have money to do those things. If you're not successful you will have learned many valuable lessons about yourself and the world to take back to a steady corporate job.

- will I be lonely/bored/feel like a loser?

No, you'll be terrified, stressed, over-worked, feel like a loser one minute shortly followed by feeling like you're king of the world. It's a roller coaster! Lots of fun.

- is it crazy to just quit without a solid plan?

No, not crazy, if that's what it takes for you to get started. However, there are many many entrepreneurial things you can be doing while you keep you old job. Firstly, network network network with other entrepreneurs. You need to be looking for ideas, problems that need solving, people with ideas looking for a business guy to make it happen. When you're not doing your day job, you should be talking with anyone who will listen about stuff. Conversations is where most business opportunities arise. Even if you have a great idea, only talking to others will really flesh it out, validate & refine it.
posted by Long Way To Go at 9:49 PM on March 2, 2010 [3 favorites]

As a consultant and business owner, I've been very thankful to have a well-paid spouse willing to put funds into the business from time to time to even out our cash flow in the first few years. I couldn't live on what I pay myself even now after a couple of years, but I believe the sacrifice will pay off in the future as the business grows, and I'm happy with the variety and challenge of my work.

My motivation to leave corporate life and become an entrepreneur was the realization that I could deliver messages as a consultant that would never be accepted from an employee... employees in my field were expected to keep their opinion to themselves if they disagreed with upper management. I'm very happy with the decision to become an entrepreneur, but sometimes miss being able to leave the office and turn my mind and activities to something totally different (read relaxing)... As a business owner, I never really leave work mentally. It's hard work, 24/7 responsibility, and I love it.

I agree with the others that you should keep your day job and work on your enterprise on the side until it grows to the point that you must give up one or the other.
posted by northernlightgardener at 9:53 PM on March 2, 2010

You don't actually have to start a venture to exercise your entrepreneurial mindset, and if you look around, form an advisory team (accountant, lawyer, HR advisor, possibly real estate agent and other specialists, as your interests might dictate), and let it be known that you're looking to take over an existing business, you'll start getting deals sent your way. The good thing will be that you'll have real operations results to evaluate, in established businesses to which you can bring talent, capital or other advantages, to make whatever business you take on more successful. You'll limit the possibility of getting lost in a morass of your own imaginative errors, and you'll build experience in business transitions, on the buyer side, which will be important later in your business career, when whatever business(es) you might own or have holdings in, will need to be sold or liquidated, to fill your needs for retirement, or estate planning.

Being successful in your first independent business venture is a lot more important to your ultimate financial success, and freedom to do additional, perhaps unrelated business ventures in the future, than I can easily describe. Suffice it to say that while some plucky individuals try and fail a number of times before hitting upon their personal formula for success, every business venture you are in that fails, takes up time and capital and yields only "experience," much of which you could get for little or nothing, simply by reading and by heeding the advice of good advisors, before getting into it.

But trying times are golden for those prepared to act. Because of tight credit, many small businesses are stretched in situations that would normally represent positive growth opportunities, or transition steps. There are good, solid businesses going at 40% of their valuations of 3 years ago, not for any other reason than the principals have developed serious health problems, and need to get out, in a time where it is tough for normal business sales to close. The reaction to new, young, dedicated ownership coming into a situation like that is unusually positive in today's market, and you might find that existing customers are very supportive, glad that they can continue with a solid vendor relationship.
posted by paulsc at 11:06 PM on March 2, 2010 [4 favorites]

Have a look at some of the older stuff on Escape from Cubicle Nation.
posted by emilyw at 12:55 AM on March 3, 2010

Your first three questions make me wonder if you really want to leave the cushy-but-certain situation you have now for the uncertainty of having your own business. Having left the corporate world over fifteen years ago to do my own gig, I can honestly say that making the break and expecting to restore your income is a fools errand. You might make more money in your own business than you did in the corporate world, but you might not. And this can vary from year to year. If you don't think gaining the freedom and self-determination available in self-employment are worth sacrificing some of the money you're currently getting, you should not make the jump.

Your last two questions are linked together. If you don't have a clear business plan, some assurance that it can work, and know that you can support yourself reasonably well if it does work, then you are crazy.

What helped me make the jump was looking at a matrix of the pluses and minuses of staying versus leaving. The only thing listed as a plus for staying was the regular salary and benefits. When I saw that, I just knew it was time to strike out on my own.
posted by DrGail at 5:05 AM on March 3, 2010

There's a lot of sensible advice given above. One big issue has not been addressed: Do you have a spouse and kids? The answer to that one question can seriously affect the computations of risk vs. rewards.
posted by megatherium at 5:54 AM on March 3, 2010

Nthing advice above.


Have it critiqued (nay, savaged) by at least 2-3 other people who you trust and who have successfully managed entrepeneurial enterprises well. Don't quit before you know you can do what you want to do with your available resources , on a feasible timescale and under the extant market conditions.
posted by lalochezia at 11:37 AM on March 3, 2010 [1 favorite]

Thank you very much for the useful thoughts - both the constructive and inspiring.

I am single, no kids (also female, incidentally). I also have a side job working for someone who runs her own business and make enough to live on at that job, and it's very minimal hours. I would continue doing that job while I start my venture. However, I do have some financial loose ends I'd like to clean up (student loans mostly) and also know that a business plan in place would be the best course of action before quitting the day job.

Intellectually, I know I should wait to make my move. Emotionally I'm on a bit of a roller-coaster because my boss is very difficult for me to deal with, and I often wonder why I'm bothering with the mental effort required. I think that like anything else, this management/leadership experience will be a great lesson that I can bring to my enterprises in the future. Tough to actually feel it in the present moment.

A few other clarifications: I have a business education (so no need for community college). Several of my family members own their own businesses, and like I said I work for someone who owns her own business as a side thing. so I'm pretty close to it (actually, it looks amazing, I would love her business). I love food, but am not starting a restaurant or any other consumer facing business, it would be a business to business enterprise based on my current skill set (negotiations, strategy), with the form of the business TBD.

I'm very intrigued at the idea of buying an existing business - I will research further.
posted by rainydayfilms at 9:55 PM on March 3, 2010

I too left my high paying corporate job to launch my own start up (this is now four weeks ago) and I can honestly say that so far I have never looked back, however, my emotions at the very beginning ranged from totally elated one moment to scared the next. The fear has started to subside as the business is beginning to grow and I am sure that it will minimise day by day.

Leaving a good job is never an easy decision to make but I was so sick of just going through the motions as oppose to living - never had time to do any of the things I wanted to. When finally making the decision to take the leap I considered the following: What would I regret most when I am an old lady and reflect back on my life - the things I did do or the things I didn't do? I would only regret the things I didn't do because the things I did do would have a tangible outcome (either good or bad) but still an outcome.

I wish you all the best of luck with your future decision - have faith in yourself and remember the saying "Leap and the net will appear"
posted by jomorome at 2:51 AM on March 4, 2010 [1 favorite]

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