Making the jump from the career world to the world of earning your own way in the world is a traumatic choice for many.

Far too many (and I count myself amongst this group) first ended up there not by choice, but by circumstance. A “mid-life course correction”, so to speak, brought about by the decisions of others.

But suppose, for a moment, you’ve decided this will be a part of your future. Are there reasons to delay jumping in with both feet?

If you’re just starting out

Coming out of school and going straight into entrepreneurial life can be very rewarding. (Indeed, an increasing number of people I meet at technology industry conferences that are doing startups are still in school even while they’re building out their companies.)

The big thing I see, from years of mentoring and advising entrepreneurs, is that the fewer obligations you have personally the better off starting out will be.

Doing a start up while trying to repay six figures’ worth of student debt, for instance, might be the breaking factor for the success of the venture. Doing it without any, on the other hand, would make it possible for you to reduce your draw on the venture, ploughing time and earnings back into it.

There are transitions in new ventures — that moment when you absolutely have to bring another person in to cope with the work, for instance — where being able to do so without letting your own pocketbook needs get in the way really helps.

If you’re in school, and thinking about an independent life after it, come out with as few outstanding “ties to your past” as you can.

At the same time, you’ve just removed the biggest worry about school from your back: the “will this course selection, will this degree, get me a job?!?” So take what helps you, broadens you, makes you better suited to turn ideas into reality.

If you do need to seek employment a few years from now, you’ll have that venture on your résumé — and that will come ahead of your degrees.

End of working life

For those of us past fifty years old and perhaps facing (or recently put through) one of those lovely “let’s shed cost early retirement programs”, it can be difficult to find a new position. The idea of self-directed working starts to take hold as a good idea — you’re not ready to retire, after all.

Oddly enough, for many of us, this is almost as good a time to chart a new course as coming out of school is. But there are a few things to think about.

First, if you do, you’re probably on that road until you decide to hang it up altogether. It’s a nasty (but true) fact of life that “trying your hand at being an entrepreneur” is less damaging to your résumé at 25 than it is at 55. At 55, what it says is “couldn’t find work” — whether that’s the case, or not.

And, alas, whereas a young person at 29-30 looking for a job can be slotting into an entry-level position without too much worry, an ex-senior manager coming back to corporate life at 59-60 is seen as having lost their “corporate edge” — not because of age, but because the challenge of running your own show has probably raised your independence levels to heights that would challenge too many around you.

So, if you’re taking this path at this age, it’s important to clear the decks, since although you may have more than one venture before you hang it up for good, you will be in venture mode from here on in. If you’re fortunate enough that your children are grown and actually moved out, now’s the time to downsize, free up cash (save it, you don’t have years left to put money away for retirement) and, in essence, make it possible to live on far less cash flow so that your business can grow.

If you are the sole earner in your family — or your spouse is already on the self-employed track — this is even more important. The reason? Lack of corporate benefits, chief amongst them extended health coverage. So the other part of self-employment at the end of a career is that you must take your health into your own hands, and work hard to minimize your costs in this area.

Mid-career entrepreneurial zone

For those somewhere in between these two poles (let’s say 35-45 as a talking point) the mid-career change is the toughest problem of all to crack.

You’re at the height of your financial responsibilities, your family’s still growing, and yet you’re now old enough that, just like your 55-year-old cousin, going off now can easily become a one-way trip to “permanent unemployability”, where working for yourself is your main future to the end of your working days.

Here is the zone, in other words, where managing your personal security so that you don’t find yourself having to make a forced decision is really your first priority. (Obviously, if you’re making a conscious choice and doing so with your eyes open, that’s a different situation.)

What all of these examples show is that thinking of your life as a portfolio of things done rather than a career ladder, or trying to seek security via being the boss rather than working for something large enough to be “safe”, comes at a price.

While there may be “no free lunch”, there are ways to manage risk and move with surety no matter where you are. That’s where PDD can help. Give us a call or write an email and we’ll discuss what a personalized advisory program would look like for you.