Some of you may recognize Dana of Aspyre Solutions from her guest post here on Create Hype.  She happily agreed to share even more of her wisdom and inspiration with us in an interview.  Today she lays down how she’s reached her 4th career change (and why she loves it) and some great tips on how to make a switch from a 9-5 job to an entrepreneurial one of your own!  I know you’re going to love it.

In case people don’t know about you and your amazing business, would you mind sharing what you do?

Surely. I’m a small business consultant, and my alter ego is a freelance illustrator.  In the former, I work with people who are trying to get out of the “9 to 5” environment, who want to make a total career shift, and set out as independent freelancers and entrepreneurs and start their own businesses.  My background has always been steeped in the creative industry, working with professionals in advertising, marketing design & multimedia, and helping them navigate different areas of career transition, find jobs, understand the mechanics of running and being a small business, and really pursuing the type of work that they identify with creatively.  I call myself an “entrepreneurial wingwoman.” I think it gives a good visual of what I do.

You’re on your 4th career!  What do you love most about your newest job? 

I love that I’m always developing something new, while also fine-tuning the parts of my job that I do best.  As I mentioned, I’ve always been involved in the creative industry, so being a freelance illustrator alongside working with folks to help them launch their own businesses is the perfect compliment, and you can diversify your career like that when you work for yourself.  One of the things I’m big on is the idea that your career isn’t defined by one singular skill or concentration, i.e. “I’m a sales person”.  We all bring multiple passions and talents to the table, and I try to help people create a career situation that takes all of those critical pieces into account and finds some kind of weird harmony.  I love business, and I also love art – the one thing I’ve learned is that neither of those things can exist separately from one another if I’m going to be truly fulfilled in this lifetime.  There’s no reason you can’t have multiple pieces to your “brand” that do completely different things.

So many entrepreneurs are making the switch (like you did) from working for others to working for themselves.  What advantages does this past experience off new entrepreneurs?

Again, it’s about defining a career environment that works for you, really taking all of your core strengths and talents and capitalizing off of them in a way that works for you, and not for someone else.  Working for yourself is a constant exercise in creativity and branding – what do you bring to the table, how do you want to package that and offer it, and how can you keep evolving it into something better and better that you love doing?

It’s a very scary transition at first, especially if you’re coming from the 9 to 5 world where many of us are trained to fit into a certain mold, whether that’s defined by our company culture or our job description.  It’s almost like going through a breakup, but without all the hard emotional feelings, in terms of what do you suddenly do with all this new freedom, all this space to reinvent yourself?  It can be overwhelming.  But once you clarify your ideas, and your vision for your business and really have a sense of what your goals are and where you want to go, it becomes a really exciting and rewarding process.  No other career really welcomes the process of trial and error like being an entrepreneur does – I love that.

We all want to make a career transition as quickly as possible but sometimes that’s not the best option.  Do you have a short list of things business owners should consider when planning a career change?

You never want to make that kind of transition or decision out of desperation.  There’s a big difference between wanting to change jobs, and wanting to change careers.  Unemployment issues, or job dissatisfaction are indicators that maybe it’s just a different job that you’re seeking.  Don’t start a business because you feel like you have no other options, or are tired of job searching, or are simply tired of doing what you’re doing.  People do it, I’m sure, but I don’t recommend it.  You need to have clarity, motivation, passion for your ideas and goals.

You also need to figure out what your personal brand image is all about.  If you’re trying to reinvent yourself, either as an entrepreneur or in a new career field, you need to create a new brand identity around that skill set.  I was a recruiter in another lifetime, and while I still have some great skills that I carry over from that career, my small business clients don’t really care about that.  My brand isn’t about what I did previously, no matter how long it was for; it’s about what I can do for this new audience that I’m trying to reach and the value I have to offer them.  They don’t care that I spent X years in recruiting.  Chances are you’re making a career change because you know you have certain skills that are transferable, or some kind of connection to that new industry that you can play off of and start marketing.  You need to create a clear brand around this “new you” that clearly communications to your target audience, whether it’s HR or potential customers, the value that you bring to the table in terms of your skills, talent and expertise.

And finally it’s important to surround yourself with positive people who support your ideas and your desire to make such a transition.  Especially starting a business and working for yourself, you’re going to encounter plenty of nay-sayers among friends and family who think you’re crazy, risking too much, or are simply jealous of your balls to strike out on your own, and will put you down for it.  But surrounding yourself with other people who are doing similar things, fellow freelancers or entrepreneurs, people who you can talk to about your ideas with complete enthusiasm and joy, those are the people you want in your circle.  Starting a business can be a very difficult thing at times, and when you get pissed off, beat down or start to lose motivation, you need people there to sometimes remind you of all the positive things you done, and essentially be your cheerleader.

You and your business have evolved so much over the past few years.  Was there ever a time where you worried about failing or met a hard obstacle?  How did you overcome it and push forward?

In all honesty, even when you’re doing well, I don’t think you necessarily stop worrying about hitting obstacles or potentially failing.  In the first year or so, your business is constantly evolving, and sometimes that can be scary.  I started this business doing just career consulting, and when I started to pivot away from that and more towards working with aspiring entrepreneurs and business development, I definitely saw a dip in business.  My audience was so accustomed to seeing me write articles and advice focused around job searching, and suddenly I’m talking about incorporation and start-ups.  And I worried, like “what if this new focus doesn’t catch on quick enough, and the revenue I was making on the career end starts to dwindle faster than the small business end picks up?”  But that’s a natural part of allowing your business to evolve.  I really wanted to focus more on small business, so I had to just ride that wave out.

When times got tough I reminded myself why I’m committed to doing the work that I do in the first place, and it helps me reconnect with my motivation.  I’m not just someone who started a business and now qualifies herself to tell someone else how to start a business based on my model, so I can make a few bucks off of my knowledge.  I actually love talking about business in general – running one, starting one, creating brands.  I’m actually really boring and can sit there for 2 hours talking about small business taxation and other laborious things most people have zero interest in, but that’s because it’s my passion.  I find it exciting.  Same thing with art.  I’m not just jumping on a bandwagon and going after freelancers as a target market.  I AM a freelancer myself, I’ve been an artist for almost 30 years, I’m an illustrator, and I love working with other people who appreciate creativity, and want to build a career around it.  In short, I’m a big nerd… and I wouldn’t change it!

If you’d like more information on making a career-change or want your own Entrepreneurial Wing-Woman, check out Dana’s site, Aspyre Solutions.